WO2006037279A1 - Support d'enregistrement pour memoire operationnel tridimensionnel - Google Patents

Support d'enregistrement pour memoire operationnel tridimensionnel Download PDF

Info

Publication number
WO2006037279A1
WO2006037279A1 PCT/CY2005/000003 CY2005000003W WO2006037279A1 WO 2006037279 A1 WO2006037279 A1 WO 2006037279A1 CY 2005000003 W CY2005000003 W CY 2005000003W WO 2006037279 A1 WO2006037279 A1 WO 2006037279A1
Authority
WO
WIPO (PCT)
Prior art keywords
photochromic
bis
optical
fulgimides
light
Prior art date
Application number
PCT/CY2005/000003
Other languages
English (en)
Inventor
Valery Alexandrovich Barachevsky
Vadim Veniaminovich Kiyko
Michail Mikhailovich Krayushkin
Sergei Igorevich Lyiksaar
Evgeniy Nikolaevich Oftiserov
Yurii Alexandrovich Puankov
Felix Markelovich Stoyanovich
Yurii Petrovich Strokach
Tatyana Michailovna Valova
Original Assignee
Akiram Trading Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Akiram Trading Limited filed Critical Akiram Trading Limited
Publication of WO2006037279A1 publication Critical patent/WO2006037279A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
    • G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds
    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
    • G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
    • G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only

Definitions

  • the present invention generally concerns fulgimides and photochromism.
  • the present invention particularly concerns a new thermal stable photochromic bis- fulgimides.
  • the present invention relates to the field of photochromic materials, in particular, to photo- chromic compounds and matrices suitable for use in working optical memory systems, including three dimensional optical memory systems for computers, multimedia applications and the like.
  • the present invention is related to devices of three-dimensional optical memory namely to devices for writing-erasing-reading of information within a 3D optical registering medium.
  • the applied devices may be used in all areas of computation where required is storage of big massive of information with possibility of its multiple re-writing. Also, possible is usage of this device for recording, storage and playing of video- and audio-files.
  • Photochromic fulgimides as related fulgides, a classes of organic compounds which are capable of reversible light-induced coloration, were developed by several research groups (J.D. Margerum, LJ. Miller. In: Technique of Chemistry. Photochromism. V.III. Ed. G.H. Brown. J.Wiley and Sons. N. Y. 1971. P.557; H.G. Heller. In: Fine Chemical for the Electronic Industry. Ed. P. Bamfield. Royal Soc. Chem. London.1986. P.120; J.Whittall. In: Photochromism: Molecules and Systems. Amsterdam. 1990. P.467; J.Whittall. In:
  • Photochromic fulgimides exhibit several important physical properties, such as thermal stability of both colorless and colored forms, high photoreaction efficiency, high fatigue resistance to repeated coloration-bleaching cycles and light power. Photochromic fulgimides are promising candidates for many technological applications including use in recording media, particularly in erasable optical memory devices. See M.Fan et al. In: Organic
  • the colored form of the photochromic material will desirably the photoinduced absorption, fluorescence or refractive index fluoresce when illuminated with light.
  • heterocyclic photochromic fulgimides are thermally stable, fatigue-resistant and undergo near-quantitative conversion to their colored forms upon exposure to UV light.
  • these photochromic fulgimides do not provide high light-sensitivity (M.Fan et al. In: Organic Photochromic and Therrnochromic Compounds. Eds. J.C.
  • This invention relates to making one or two-photon photochromic recording media for 2D or 3D working optical memory possessing bit recording.
  • photochromic recording medium namely amplitude recording medium due to the photoinduced absorption as well as phase and fluorescence recording media which exhibit photoinduced refraction and fluorescence during photochromic transformations, correspondingly.
  • photochromic transformations may be realized under one or two- photon absorption processes.
  • a photochromic material in all these devices changes color when irradiated with UV, visible or infrared irradiation while in the ground state.
  • the light is adsorbed by the ground state molecule, which then undergoes a photochemical reaction to form the photoinduced form.
  • the photoinduced state absorbs light at a different wavelength than the ground state of a molecule.
  • the photoinduced form reverts to the initial form by thermal reversion or by being irradiated with light again, preferably light with a different wavelength than the light used to "read" the photoinduced form.
  • the photochromic compound is incorporated within a 2D or 3D matrix that is transparent to the activating light.
  • the recording medium then is irradiated, preferable by a laser to photochemically change the light absorption of the photochromic recording medium at a site.
  • the 2D or 3D memory device "reads" the information by irradiating the sites with light at a wavelength for which the photoinduced state has a high absorption, index refraction or fluorescence yield.
  • the information associated with a location can be erased by irradiation thereof with light having wavelength causing reverse photochemical change the photoinduced state B back to the ground state A.
  • the recording media should combine a multitude of physical-chemical properties simultaneously. Among these properties we can distinguish the most evident and simple ones
  • -molecules of the active photochromic recording media shall be adequate photochromic i.e. absorption bands of form A and form B shall have bigger extinction coefficients and shall not overlap;
  • -forma B of photochromic substance should the low change of the adsorption band during read-out of optical information; -reversible transformations between forms A and B shall be characterized by high recurrence (more 10 4 cycles without any noticeable changes of optical density at the maximum of the photoinduced absorption bands).
  • optical memory devices including 3D optical memory described by Rentzepis in U.S. Pat. No. 5,268,862, and Rentzepis and Esener in U.S. Pat. No. 5,325,324, herein incorporated by reference, a three dimensional laser disc drive system described by Goldsmith et al. in U.S. Pat. No. 5,113,387, herein incorporated by reference, optical memory system and method described by Lindmayer in U.S. Pat. No. 4,864,536, herein incorporated by reference and optical system.
  • Another three-dimensional optical storage memory system is described by Parthinopoulos et al. (Science, Vol. 245,843,1989), also incorporated herein by reference.
  • diarylethenes The synthesis and properties of diarylethenes was reviewed by M. Me (M.Irie. In: Organic Photochromic and Thermochromic Compounds. Eds. J.C. Crano and RJ. Guglielmetti. N. Y. and L., Plenum Press. 1999. V.I. P. 207; Chem. Rev. Vol. 100, 1685, 2000).
  • the different dihetearliestthenes were used for making optical memory (T.Tsujioka. Mol.Cryst.Liq.Cryst, Vol. 344, 51, 2000; T. Fukaminato et al. Proc. JPN Acad. Ser. B, Vol. 77, N. 2, 30, 2001; Z. Liang et al.
  • Proc.SPIE Vol. 4930, 134, 2002; X.Mai et al., Proc. SPIE, Vol. 5060, 270, 2003; HXi et al., Proc. SPIE 5 VoI. 5060, 279, 2003; Y. Yokotama ET AL., J. Am. Chem. Soc, Vol. 125, N 24, 7194, 2003.
  • the majority of the recording media for 2D or 3D optical memory uses fluorescent readout of optical information. But the written information may be accessed by the detection of the changes in refractive index ( T. Kardinahl et al. Appl. Phys. A. Vol.61, 23, 1995), IR spectra (M. Seibold et al. Chem.Phys.Lett. Vol.225, 135, 1996), photocurrent (T.Tsujioka et. Al. J.Opt. Soc. Amer. Vol. 19, N 2, 297, 2002), molecule design (E.Murguly et al. Angew. Chem. -Intern.Ed. VoI 40, N 9, 1752, 2001; AJ.
  • the one problem associated with the use of the proposed spiropyrans as photochromic substrates in working optical memory devices lies in the fact that their photoinduced form is not thermally stable and is capable to revert to the ground state by itself.
  • the matrix carrying these photochromic materials must be cooled to at least -78 C. and preferably lower temperatures. Necessity in such low temperatures as a precondition for efficient functioning of devices utilizing above materials is associated with difficulties in design and limits the scope of possible applications.
  • spyropyrans usually lose their photochromic properties after a few read — write - erase cycles.
  • the other problem is a low light-sensitivity of the photochromic organic media because of the absence any catalytic process for receiving image and restriction solubility ob the photochromic compounds in the polymer binders. This leads to low concentration of light- sensitive centers and, consequently, to low information capacity of the recording medium and optical memory.
  • the analog of this invitation is a photochromic materials, in particular, based on photochromic compounds from spiropyran class and polyester as matrix suitable for use in optical memory systems, including three-dimensional optical memory systems for computers, multimedia applications and the like.
  • nonfmorescent spiropyrane is transformed into fluorescent merocyanine by electromagnetic radiation.
  • the progenitor of this invitation is a photochromic material, in which N-(4-Phenyl)-3-[l- (2,5-dimethyl-3-thienyl)-ethylidene]-4-isopropylidene]pyrrolidine - 2,5-dione (Ryoka Matsushima, Hiroshi Sakaguchi. J. Photochem. Photobiology. A: Chemistry. Vol. 108, 239, 1997) is used in the polymer binder.
  • the second state of photochromic substance produces fluorescence under action of radiation of wavelength 1064 nm, i.e. irradiating the volume by this radiation makes it possible information readout by scanning of fluorescent locations. Erasing is achievable by heating medium locally or entirely e.g. by radiating thereof by 2.12 ⁇ beam. Disadvantages of this facility are similar to those of previous one. Since the write-process is two-photon type, necessary are radiation sources of high peak power, consequently operating at relatively low frequencies. Necessity of positioning of two mutually perpendicular beams into the three- dimensional volume of medium sets limits of a voxel dimensions by units or tens microns, the possible focusing spot being of sub-micron size. Besides homogeneity and surfaces confining the volume must be of high optical quality, the latter could be relatively easy achieved in the cases of glass or crystal matrices. For polymer, obtaining of similar quality at mass- production is problematic or will result in costs increase.
  • a method to overcome this disadvantage is to apply method of confocal microscopy [A. Toriumi, J.M. Herrmann, S. Kawata, Nondestructive readout of a three-dimensional photochromic optical memory with a near-infrared differential phase-contrast microscope. - Optics letters, v.22(1997), #8, 555- 557].
  • This method enables to detect variations of refraction coefficient in the recorded area.
  • radiation of wavelength at the very wing of absorbance band i.e.
  • the facility comprises optical medium positioning facility, radiation sources generating at two wavelengths ⁇ i, ⁇ 2 , optical beam forming system, facility for positioning optical beam, optical radiation detector.
  • the facility is intended for writing into two-photon medium by means its irradiation by ⁇ i beam, the writable component being mixed with signal component comprising medium fluorescent under single-photon absorption only in "recorded" state absorbing reading light quanta of wavelength ⁇ 2 .
  • Photosensitive medium comprises a multilayer structure of alternating photosensitive and non-photosensitive layers selection thereof may be performed either by spatial positioning of the storage volume or by adjustment of focal length of read- write head.
  • the non- photosensitive layers may comprise optical wave-guides along which propagated is radiation of "read" wavelength. In this case, selection of read layer is fulfilled by directing the radiation only into the being read layer. Disadvantages of this approach is similar to previous: usage of two-photon medium, and, correspondingly, need of high-power radiation sources.
  • Fluorescence used for readout imposes limitations on voxel dimensions to provide acceptable intensities of signal at the "read” process.
  • Use of wave-guide for selection of read layer though solves problem of "read” beam positioning however propagating along the wave-guide light penetrates through separation boundary for 0.5 wavelength hence the required volume of fluorescent material may be obtained only owing to increase of the voxel transverse dimensions and, correspondingly, decrease of recording density.
  • Use of single-photon processes inevitably results in partial erasing in each reading act, to avoid this influence the medium is doped with up-converting the radiation component.
  • the present invention contemplates photochromic bis-fulgimides that are characterized by photoinduced absorption and refractive index under irradiation of an appropriate frequency.
  • the photochromic fulgimides of the present invention are particularly suitable for optical memories.
  • the photochromic bis-fulgimides of the present invention exhibit all the important physical properties of photochromic bis-fulgimides; to wit: thermal stability of both colorless and colored forms, high photoreaction efficiency, high fatigue resistance to their repeated coloration-bleaching cycles and light power. Moreover, they are characterized by high photoinduced absorption and refractive index in one (only) stable form.
  • the present invention is embodied in a photochromic chemical consisting essentially of colored heterocyclic bis- fulgimides.
  • the present invention is embodied in heterocyclic photochromic bis ⁇ fulgimides consisting essentially of colored derivatives 1,4 - phenylene-bis ⁇ 3-[l-(2,5- dimethyl-3-thienyl)ethylidene]-4-isopropylidene ⁇ pyrrolidin- 2,5-dione capable of excitation by at least ultraviolet light to absorption and refractive index.
  • heterocyclic photochromic fulgimides are preferably synthesized by process of (1) condensation of acetone with diethylsuccinate in fert-butanole at the presence potassium tert- butylate, (2) condensation of 3-acetyl-2,5-dimethyl-thiophene with 3-isopropylidene- diethylsuccinate at the presence of potassium f ⁇ rt-butylate in toluene according to Stobbe reactions and following alkaline hydrolysis of obtained diester, (3) cyclization of 2-[ ⁇ -(2,5- dimethyl-3-thienyl)ethylidene]-3-isopropyliden-succinic acid into cyclic anhydride (fulgide) at the presence a new cyclising agent diethyl chlorophosphate in dry dimethylformamide, (4) interaction between fulgide and aromatic diamines, (5) cyclization of diamides of 1,1- carbonyldiimidazole in dry tetrahydro
  • the main object of the present invention is to provide a new and improved photochromic recording media having physical and photo-chemical properties for use of these materials in available 2D or 3D optical memory storage devices based on absorption and refraction reading.
  • Another object of the present invention is to provide a new and improved photochromic recording media defined by high information capacity and which are thermal stable in use and photochemical stable in reuse (read-write-erase cycles) and in which the reading of the information based on absorption or refraction.
  • Another object of the present invention is to provide new and improved recording medium having increased light-sensitivity value at room temperature.
  • Another object of the present invitation is to provide new and improved recording media having increasing of the concentration of the light-sensitive centers in volume of recording media.
  • the medium material having the above improved properties comprises a light sensitive photochromic polymeric compositions based polycarbonate or polystyrene and one of bis-fulgimides.
  • Another object of the present invention is facility for information writing-erasing-reading in a multi-layer registering medium based on the 2 wavelength full solid state diode pumped laser intended to overcome the problem of information erasing in the writing medium at reading.
  • FIG. 1 shows the structure of the synthesized photochromic bis-fulgimides.
  • FIG.2. shows the structure of mono-fulgimide analog , namely N-(4-Phenyl)-3-[l-(2,5- dimethyl-3-thienyl)-ethylidene]-4-isopropylidene]pyrrolidine - 2,5-dione
  • FIG. 3 is a diagrammatic view showing the reversible photoisomerization, ultimately generating the cyclic structure B from open form A shown on FIG. 1, undergone by the synthesized bis-fulgimides of the present invention when illuminated with UV and visible light.
  • FIG.4 us showing the structures of synthesized bis-fulgimides
  • FIG. 5 is a diagram showing the stepwise process of synthesizing the bis-fulgimides on the present invention.
  • FIG. 6 is a Table 1 showing the chemical data characterizing the synthesized bis-fulgimides.
  • FIG. 7 is a Table 2 showing spectral-kinetic characteristics for synthesized bis-fulgimides and mono-fulgimide analog (FIG.2) in toluene.
  • FIG. 8 is showing the absorption spectra before (1), after UV irradiation (2) for mono- fulgimide (FIG.2) analog of bis-fulgimides in toluene.
  • FIG. 9 is showing kinetic curves for photocoloration under UV irradiation (1) and photobleaching under visible irradiation (2) for mono-fulgimide analog (FIG.2) in toluene.
  • FIG. 10 is showing the absorption spectra before (1), after UV irradiation (2) for bis- fulgimide 7c in toluene.
  • FIG. 11 is showing kinetic curves for photocoloration under UV irradiation (1) and photobleaching under visible irradiation (2) for bis-fulgimide 7c in toluene.
  • FIG. 12 is showing the absorption spectra before (1), after UV irradiation (2) for bis- fulgimide 7a in toluene.
  • FIG. 13 is showing kinetic curves for photocoloration under UV irradiation (1) and photobleaching under visible irradiation (2) for bis-fulgimide 7a in toluene
  • FIG. 14 is showing the absorption spectra before (1), after UV irradiation (2) for bis- fulgimide 7b in toluene.
  • FIG. 15 is showing kinetic curves for photocoloration under UV irradiation (1) and photobleaching under visible irradiation (2) for bis-fulgimide 7b in toluene
  • FIG. 16 is showing the absorption spectra before (1), after UV irradiation (2) for bis- fulgimide 7d in toluene.
  • FIG. 17 is showing kinetic curves for photocoloration under UV irradiation (1) and photobleaching under visible irradiation (2) for bis-fulgimide 7d in toluene.
  • FIG. 18 shows structural chemical formulae of bis- fulgimides (F2-F5) found as suitable for use in working optical memory systems in accordance with the present invention and mono- fulgimide analog (Fl)for comparative study.
  • FIG. 19 shows UV- visible spectra of recording media in accordance with the present invention before (1) and after (2) exposure to UV light irradiation for mono-fulgimide analog Fl in polycarbonate.
  • FIG. 20 is showing kinetic curves for photocoloration under UV irradiation (1) and photobleacing under visible irradiation (2) for mono-fulgimid analog F 1 in polycarbonate.
  • FIG. 21 is a Table 1 showing spectral-kinetic characteristics for synthesized mono - and bis- fulgimides in polycarbonate.
  • FIG. 22 shows UV-visible spectra of recording media in accordance with the present invention before (1) and after (2) exposure to UV light irradiation for mono-fulgimide analog Fl in polystyrene.
  • FIG. 23 is showing kinetic curves for photocoloration under UV irradiation (1) and photobleacing under visible irradiation (2) for mono-fulgimid analog Fl in polystyrene.
  • FIG. 24 is showing the absorption spectra before (1), after UV irradiation (2) for bis- fulgimide F2 in polycarbonate.
  • FIG. 25 is showing kinetic curves for photocoloration under UV irradiation (1) and photobleacing under visible irradiation (2) for bis-fulgimide F2 in polycarbonate.
  • FIG. 26 is showing the absorption spectra before (1), after UV irradiation (2) for bis- fulgimide F3 in polycarbonate.
  • FIG. 27 is showing kinetic curves for photocoloration under UV irradiation (1) and photobleacing under visible irradiation (2) for bis-fulgimide F3 in polycarbonate.
  • FIG. 28 is showing the absorption spectra before (1), after UV irradiation (2) for bis- fulgimide F4 in polycarbonate..
  • FIG. 29 is showing kinetic curves for photocoloration under UV irradiation (1) and photobleacing under visible irradiation (2) for bis-fulgimide F4 in polycarbonate.
  • FIG. 30 is showing the absorption spectra before (1), after UV irradiation (2) for bis- fulgimide F5 in polycarbonate.
  • FIG. 31 is showing kinetic curves for photocoloration under UV irradiation (1) and photobleacing under visible irradiation (2) for bis-fulgimide F5 in polycarbonate.
  • FIG. 32 shows an experimental optical setup for testing of the photochromic recording medium sample.
  • FIG. 33 a-c Experimental setup for the diode-pumped Nd:YVO4-laser with forth harmonic generation
  • FIG. 34 The average power, the pulse energy and the duration versus the repetition frequency.
  • FIG. 35 Block diagram of recording-erasing-reading facility.
  • a new class of thermally stable and fatigue resistant photochromic bis-fulgimide derivatives have been synthesized.
  • the absorption spectra, light-sensitivities, kinetic of the photochemical reactions (photocoloration, photobleaching, photodegradation) of these bis-fulgimides as compared with a mono-fulgimide analog were measured.
  • the absorption spectra of initial open A and photoinduced cyclic form are acceptable for one- and two- photon excitation.
  • the both forms are thermal irreversible.
  • the light-sensitivity for the synthesized bis-fulgimides is more that for mono-fulgimide analog.
  • Bis-fulgimides are characterized by more effective stability to irreversible photochemical transformations. They provide the high recurrence of the photochromic transformations, which exceeds 10 cycles.
  • the present specification concerns the synthesis and the photochromic behavior of these 4 bis-fulgimides as compared with the mono-fulgimide analog.
  • the light-sensitivity of synthesized bis-fulgimides exceeds the same value measured for a mono- analog.
  • Some different species of bis-fulgimides described above were synthesized and unambiguously identified by means of NMR 5 MS-spectra and elementary analysis.
  • the photochromic bis-fulgimides of the present invention have high reversible photochemical reaction efficiency, high thermal stability when irradiated with visible light.
  • Bis-fulgimides are derivatives of thienylfulgimides containing two thienylfulgimide fragments linked by the aromatic bridges of different type (FIG.l).
  • FIG.2 The structure of mono-fulgimide analog (FIG.2) is N-(4-phenyl)-2-[l-(2,5-dimethyl-3- thienyl)-ethylidene]-3-isopropyliden - 2,5-dione (Ryoka Matsushima. J. Photochem. Photobiol. A: Chemistry, Vol.108, 239, 1997).
  • Photochromic bis-fulgimides form a 4n+2 system (FIG. 3,A).
  • open-ring form A known as colorless form
  • a conrotatory ring-closure reaction occurred according to the Woodward-Hoffman selection rules (FIG. 3,B). This results in the formation of a cyclized structure (known as colored form or B form) whose absorption spectrum is red shifted to the visible region.
  • Photochromic bis-fulgimides 7a-d are prepared from 3-acetyl-2,5-dimethyl-thiophene by the five-stage synthesis.
  • the subject compounds of the present invention have been synthesized according to the following process (FIG.5).
  • the preferred process of the present invention for obtaining of 1,4 - phenylene-bis ⁇ 3-[l-(2,5- dimethyl-3-thienyl)ethyliden]-4-isopropyliden)pyrrolydine - 2,5-dione and its analogs includes (1) condensation of acetone with diethylsuccinate in f ⁇ rt-butanole at the presence potassium tert-butylate, (2) condensation of 3-acetyl-2,5-dimethyl-thiophene with 3- isopropylidene-diethylsuccinate at the presence of potassium fert-butylate in toluene according to Stobbe reactions and following alkaline hydrolysis of obtained diester, (3) cyclization of 2-[ ⁇ -(2,5-dimethyl-3-thienyl)ethylidene]-3-isopropyliden-succinic acid into cyclic anhydride (fulgide) at the presence a new cyclizing agent diethyl chlor
  • Stage 2 Preparation 2-[ ⁇ -(2,5-dimethyl-3-thienyl)ethylidene]-3-isopropylidensuccinic acid.
  • the residue is extracted by chloroform three times by portions of 70 ml.
  • the organic layer is separated , dried with CaCl 2 .
  • the solvent is evaporated.
  • the residue dissolved in 100 ml of 10% KOH ethanol solution and hydrolyzed during 7 hours, then solvent is evaporated.
  • To the residue 100 ml of water are added and acidified .
  • Diacid is extracted by chloroform.
  • the organic layer is separated , dried under CaCl 2 and is evaporated.
  • the residue is dark-brown ductile oil.
  • 200 ml of petroleum ether and 30 ml diethyl ether are added .
  • the precipitated crystals are filtered off , washed by petroleum ether with the use of the Shott filter an dried in the vacuum. 11,98 g (44%) of the white crystals of diacid 5 (m.p. 203-205 0 C) are obtained.
  • Stage 3 Synthesis of [ ⁇ -(2,5-dimethyl-3-thienyl)ethylidene]-3-isopropylidenesuccinic anhydride.
  • Eluent is the mixture of hexane-ethylacetate (2:1). After evaporation of solvent 0.43 g (38 %) light red crystals of bis-succinimide , m.p. 258-260 0 C (chloroform- petroleum ether). Mass spectrum, m/z (/ rel, %): 624 (87). Found, % : C-68.91 %, H-5.80 %, S-10.17 %. C 36 H 36 N 2 O 4 S 2 . CaIc, % : C-69.20 %, H-5.81 %, S-10.26 %. Data are present in Table on FIG. 6.
  • the stages 1-3 described above is a general method for the obtaining of key compound ⁇ . This compound has been used in the synthesis of bis-fulgimides 7a, 7b, 7d.
  • the synthesized bis-fulgides-7a-7d were, found, when illuminated with UV light, to undergo reversible photoisomerization.
  • a diagrammatic view of this reversible photoisomerization of the present invention is shown in FIG. 3.
  • Photoisomerizable molecular structures "A” and "B” are each shown in FIG. 3.
  • the structure of molecular species B which undergoes cyclically reversible photoisomerization, also called photocylcyclization, is diagrammatically illustrated on FIG. 3.
  • the open colorless forms A of these compounds are characterized by absorption maxima in the region of 310-335 nm (Table 2 on FIG.7, curves 1 on FIG.8, FIG.10, FIG.12, FIG.14, Fig.16).
  • the colored forms B are characterized by absorption maxima in the spectral range of 522-535 nm (Table 2 on FIG.7, curves 2 on FIG.8, FIG.10, FIG.12, FIG.14, Fig.16).
  • the colored forms B can be reversibly bleached by excitation with . ⁇ .>400 nm visible light. During the bleaching process only the formation of the forms A were observed, which is the preferred configuration for the cyclization process.
  • absorption maxima of compounds 7a-7d are the same (530 nm) and are shifted to the long-wave visible region as compared with mono-fulgimide analog.
  • All synthesized bis-fulgimides are characterized by the similar kinetic curves for photocoloration under UV irradiation (curve 1 on FIG. 9, FIG.11, FIG.13, FIG.15, FIG.17) and photobleaching under visible irradiation (curve 2 on FIG. 9, FIG.ll, FIG.13, FIG.15, FIG.17) from the Hg-lamp possessing power of 250 W. But the light-sensitivity value for all bis-fulgimides is more as compared with mono-fulgimide analog (Table 2 on FIG.7).
  • samples of photochromic recording media were prepared according to a following procedure.
  • a light sensitive layer of photochromic medium material of 5-30 mu thickness is prepared from the thus obtained solution by method of irrigation of a Teflon cap of 5 cm diameter with subsequent drying on air.
  • the extracted colorless film in the A form is transformed to the B colored form under UV irradiation.
  • This B form may be transformed to the initial A form under visible irradiation (> 400 run).
  • This photochemical reversible transformations are thermal irreversible ones.
  • a light-sensitive layer of photochromic recording medium of 20 mu. thickness is prepared from the thus obtained solution by method of irrigation of a Teflon cap of a 5 cm diameter with subsequent drying on air. Then the prepared photochromic film is extracted from the Teflon cap. This film was irradiated at the room temperature with a UV light produced by high pressure Hg-lamp (DRS -120) from the distance of 120 cm through a glass filter. The absorption spectra and before and after UV irradiation (FIG.19) were measured.
  • the sample was irradiated by UV and visible light through the silicate glass filters transmitting and cutting UV irradiation.
  • the kinetic curves for photocoloration and photobleaching processes and are recorded (FIG.20).
  • the kinetic of thermal relaxation of UV induced form into an initial form is measured too.
  • the determined maxima absorption band for the B form, the maximum value of the photoinduced optical density characterizing the light-sensitivity of the photochromic recording medium as well recurrency of photochromic transformations are presented in Table 3 (FIG.21) .
  • the colored B form had no any changes of the photoinduced optical density during one month of dark storage. It is seen that the sample are characterized by the acceptable light-sensitivity to UV and visible irradiation well-known laser sources, practically unlimited thermal stability and may be used in 2D or 3D optical memory devices.
  • EXAMPLE 6 According to the procedures described in examples 5, the sample differing a presence of photochromic compound Fl in polystyrene was prepared and measured. The obtained data are presented on the FIG. 22 and 23 as well in Table 3 (FIG.21). It is seen that the sample are characterized by the acceptable light-sensitivity to UV and visible irradiation well-known laser sources, practically unlimited thermal stability and may be used in 2D or 3D optical memory devices.
  • the sample differing a presence of photochromic compound F2 (4,2 weight%) instead of compound Fl was prepared and measured.
  • the obtained data for the photochromic film of 20 mu thickness are presented on the FIG. 24 and 25 as well in Table 3 (FIG.21). It is seen that the sample are characterized by the acceptable light-sensitivity to UV and visible irradiation well-known laser sources, practically unlimited thermal stability and may be used in 2D or 3D optical memory devices. The light-sensitivity of this sample is more as compared with the sample prepared according to the procedures described in examples 1.
  • the sample differing a thickness of 30 mu was prepared and measured.
  • the obtained data for this photochromic film of 30 mu are presented in Table 3 (FIG.21). It is seen that the sample are characterized by the acceptable light-sensitivity to UV and visible irradiation well-known laser sources, practically unlimited thermal stability and may be used in 2D or 3D optical memory devices.
  • the light-sensitivity of this sample is more as compared with the sample prepared according to the procedures described in example 1.
  • the sample differing a presence of photochromic compound F3 (3,3 weight.%) instead of compound Fl was prepared and measured.
  • the obtained data for the photochromic film of 20 mu thickness are presented on the FIG. 26 and 27 as well as in Table 3 (FIG.21). It is seen that the sample are characterized by the acceptable light-sensitivity to UV and visible irradiation well-known laser sources, practically unlimited thermal stability and may be used in 2D or 3D optical memory devices.
  • the light-sensitivity of this sample is more as compared with the sample prepared according to the procedures described in example 1.
  • the sample differing thickness (5 mu) was prepared and measured.
  • the obtained data for this photochromic film are presented in Table 3 (FIG.21). It is seen that the sample are characterized by the acceptable light- sensitivity to UV and visible irradiation well-known laser sources, practically unlimited thermal stability and may be used in 2D or 3D optical memory devices. This sample is compares with the sample prepared according to the procedures described in examples 1 in light-sensitivity.
  • the sample differing a presence of photochromic compound F4 (3,9 weight.%) instead of compound Fl was prepared and measured.
  • the obtained data for the photochromic film of 20 mu thickness are presented on the FIG. 28 and 29 as well as in Table 3 (FIG.21). It is seen that the sample are characterized by the acceptable light-sensitivity to UV and visible irradiation well-known laser sources, practically unlimited thermal stability and may be used in 2D or 3D optical memory devices.
  • the light-sensitivity of this sample is more as compared with the sample prepared according to the procedures described in example 1.
  • the sample differing a thickness of the photochromic film (5 mu) was prepared and measured.
  • the obtained data for this photochromic film are presented in Table 3 (FIG.21). It is seen that the sample are characterized by the acceptable light-sensitivity to UV and visible irradiation well-known laser sources, practically unlimited thermal stability and may be used in 2D or 3D optical memory devices.
  • the light-sensitivity of this sample is more as compared with the samp! prepared according to the procedures described in example 1.
  • the sample differing a presence of photochromic compound F5 (3,6 weight. %) instead of compound Fl was prepared and measured.
  • the obtained data for the photochromic film of 20 mu thickness are presented on the FIG. 30 and 31 as well as in Table 3 (FIG.21). It is seen that the sample are characterized by the acceptable light-sensitivity to UV and visible irradiation well-known laser sources, practically unlimited thermal stability and may be used in 2D or 3D optical memory devices.
  • the light-sensitivity of this sample is more as compared with the sample prepared according to the procedures described in example 1.
  • the sample differing a thickness of the photochromic film (5 mu) was prepared and measured.
  • the obtained data for this photochromic film are presented in Table 3 (FIG.21). It is seen that the sample are characterized by the acceptable light-sensitivity to UV and visible irradiation well-known laser sources, practically unlimited thermal stability and may be used in 2D or 3D optical memory devices. This sample is compared with the sample prepared according to the procedures described in examples 1 in light-sensitivity.
  • the sample differing a presence of photochromic compound F5 (3,5 weight.%) instead of compound Fl was prepared and measured.
  • the obtained data for the photochromic film of 20 mu thickness are presented in Table 3 (FIG.21). It is seen that the sample are characterized by the acceptable light- sensitivity to UV and visible irradiation well-known laser sources, practically unlimited thermal stability and may be used in 2D or 3D optical memory devices. The light-sensitivity of this sample is more as compared with the sample prepared according to the procedures described in examples 1.
  • Efficient conversion of radiation to the fourth harmonics requires high-quality laser beam and high peak output power.
  • Such pulses can be produced by using Q-switch mode of generation. Both passive and active Q-switching can be used. Passive Q-switched lasers need no switching electronics and possesses reduced size of the system. Nevertheless, if the pumping conditions change, then the repetition frequency and the duration of the pulses may vary in such systems. Passive Q-switch at the output power > 1 W operates at a lower initial light transmission and possesses higher passive losses.
  • Acousto-optical shutters possess low passive losses and operate in a wide range of frequencies.
  • the drawbacks caused by a long duration of the switching process can be compensated by a properly chosen geometry of the cavity under longitudinal pumping by laser diodes, high-gain active medium, and a short length of the cavity.
  • Fig. 34a a schematic diagram is shown of Nd:YVO 4 laser with acousto-optical Q- switching for extra-cavity conversion of the radiation to the fourth harmonics. It is known, that the shortest pulse duration and highest peak power are obtained in a quasi-CW laser at the repetition frequency v ⁇ 1/ ⁇ , where ⁇ is the spontaneous lifetime of the gain medium.
  • the duration of the radiation pukes slightly varied from 7 to 8 ns at the half-height.
  • the peak output power is ⁇ 3.6 kW.
  • the average power P, the energy E and the duration r of the radiation pulses are presented versus the repetition frequency for Nd:YV04 laser with the acousto-optical Q-switching.
  • the cavity length is about 25 mm.
  • the optimum transmission of the mirror is 25% at the repetition frequency 12 kHz, which corresponds to maximum output power.
  • Fig. 34b the schematic diagram of Nd: YVO 4 laser is shown where a double-pass scheme is used for nonlinear conversion to both second and fourth harmonics.
  • dichroic (HR at the primary frequency and AR at the frequency of the harmonics) mirrors were used for focusing laser radiation into nonlinear crystals and the plane dichroic (possessing high reflectivity at the both wavelengths) mirrors for the second pass.
  • HR at the primary frequency and AR at the frequency of the harmonics were used for focusing laser radiation into nonlinear crystals and the plane dichroic (possessing high reflectivity at the both wavelengths) mirrors for the second pass.
  • the efficiency of the conversion to the second harmonics increased by 15-20 %, however, with no increase in the power of the radiation at the wavelength 266 nm. It seems to be connected with the quality of the focusing optics and non-optimal parameters of the latter.
  • Fig. 34c An interesting laser scheme is shown in Fig. 34c, where an intracavity frequency conversion in the crystal KTP is used. It is known that additional elements introduced inside the cavity increase passive losses, which, in turn, makes the laser pulse duration longer.
  • nonlinear crystal KTP of the width 1 mm for the intracavity up- conversion.
  • the nonlinear crystal operates simultaneously as a reflecting and an output mirror.
  • the nonlinear element was placed on copper arm that was thermostabilized by means of a controlled Peltier cooler. This stabilization compensates phase shifts and provides phase matching.
  • the output power of the "green" YVO4 laser with the intracavity frequency conversion and the acousto-optical Q-switching at the frequency 12 kHz increases by a factor of 1.5-2 as compared to the extracavity frequency conversion and reaches 150-230 mW.
  • the pulse duration in this case slightly increases to 10-11 ns. Hence, the peak power is also greater in this case.
  • laser operation in this configuration is not stable and requires fine adjustment of the cavity parameters.
  • the acousto-optical Q-switched diode-pumped Nd:YVO4 laser comprises a Fabri-Perot resonator as it is shown in Fig. 34. Short pulses are produced in this laser due to a compact acousto-optical Q-switch inside the laser cavity with low losses.
  • the pumping diode laser of the type ATC2529 "ATC-Semiconductor Devices, Saint-Petersburg" with the emitting area 500 x 1 ⁇ m provides the pumping energy 3 W at the wavelength 808 nm.
  • the pumping beam is first partially collimated by a cylinder lens and then focused into the laser crystal by a three-lens objective.
  • the pumping spot dimensions are 200 X 150 ⁇ m.
  • the pump diode is mounted on a thermoelectric cooler and is kept at the optimum temperature in order to match the absorption band of the laser crystal. Approximately 80% of the diode-laser output energy is collected and hits the
  • the a-cut, 1%-Nd doped 1-mm long Nd:YVO4 crystal was coated for high reflection (HR) at 1064 nm and high transmission (HT) at 808 nm from the input side.
  • the other face has antireflection (AR) coating at the wavelength 1064 nm.
  • the crystal is mounted on a copper holder.
  • the 1-cm long fused silica Q-switcher has AR coatings at the wavelength of the fundamental frequency on both faces and is driven by RF 5-W generator at the central frequency 80 MHz.
  • the mirror of the active element and the flat output coupler form a short cavity of the length 25 mm. The optimum value was determined 75%.
  • the radiation of the Nd: YVO4 laser was first up-converted to 532 nm. Intracavity (Fig.
  • the UV (266 nm) radiation is generated at the second stage.
  • FHG In the stage of intractivity FHG we used a 6-mm long BBO crystal (the type I phase matching) with AR coatings at the wavelengths of the second ant the fourth harmonics.
  • the entire facility features two independent electrically controlled attenuators (3) of beams ⁇ i, ⁇ 2 , beam forming system (6) includes chromatic aberration compensator (7).
  • the facility operates as follows: radiation of laser (1) enters into a dichroic Y-joint (20) embodied on basis of optical fiber Y-joints or of dichroic mirrors.
  • the joint has 2 outputs, at each present is radiation of only ether ⁇ ⁇ or ⁇ 2 .
  • radiation from each of outputs enters two-channel electrically controlled attenuator (3) realized as ether fiber or integrated optics device.
  • the attenuator secures independent modulation of radiation at each of wavelengths.
  • Medium positioning facility (9) secures assignment of writing-erasing-reading layer and coordinates targeting of point of writing-erasing-reading in the layer plane.
  • Operation mode (writing, erasing or reading) is chosen by radiation intensity of corresponding wavelength control by attenuators (3).
  • the attenuators are controlled as follows: at writing mode radiation power at ⁇ ⁇ is maximum, at ⁇ 2 is 0 (zero); at erasing mode radiation power at is 0 and at ⁇ 2 is maximun, for reading mode ratio of radiation power at related to one at ⁇ 2 being within the range 0.2-0.7. Reading of written information takes place by registration of reflected from optical medium signal passing through the dichroic joint (5) to the optical radiation detector (10).
  • the sample from Example 5 was studied with the goal of the development possibilities for 3D multi-layer readable and rewritable systems based on the new generation of the photochromic materials and the UV full solid-state laser with frequency conversion.
  • the experimental setup is presented at the FIG.32. After photopolymer's exposing by 266nm radiation its absorption coefficient for 532nm radiation will have to increase.
  • the ratio of average power values of the reading signal (532nm) related to the recording signal will have to be less than 0,01.
  • the absorption coefficient was recovered to initial value (erasing process). The obtained results shows that this photochromic material enables to develop the new generation of the 3D optical storage disks.
  • Application of a full solid-state laser with radiation frequency conversion to second and fourth harmonics is preferable.
  • a and B forms of bis-fulgimides obtained by scheme shown in FIG. 4 were obtained directly by condensation of the 2-[l-(2,5-dimethyl-3-thienyl)ethylidene]-3-isopropylidenesuccinic anhydride with corresponding diamines followed by column chromatography purification and then recrystallization.
  • the colored forms (B-form) of these bis-fulgimides were prepared by irradiating, with 360 ran light, the A-form bis-fulgimides in toluene or acetonitrile solution.
  • the structure and purity of the compounds obtained were ascertained by NMR, MS and elementary analysis. All the solvents were HPLC grade or spectral grade and were used without further purification.
  • Photoirradiation of the photochromic solutions was carried out using a 250 W Hg arc lamp (DRSH-250, Russia). Light of the appropriate wavelength was selected by either a monochromator or a cut off optical filter. A mini magnetic stirring bar was used to mix the solution.
  • Photoirradiation of photochromic films was carried out using a 250 W Hg arc lamp (DRSH- 250 , Russia).
  • Light of the appropriate wavelength was selected by cut off glass optical filters UFS-2 and ZS- 12 (Russian samples) transmitting UV and visible (>400 urn) light for photocoloration and photobleaching, correspondingly
  • the absorption coefficient was recovered to initial value (erasing process).
  • present invention will be recognized to be embodied in a photochromic chemical consisting essentially of colored heterocyclic bis-fulgimides, and in a method of preparation of such heterocyclic bis-fulgimides.
  • heterocyclic photochromic bis-fulgimides are synthesized by process of (1) condensation of acetone with diethylsuccinate in fert-butanole at the presence potassium tert- butylate; followed by (2) condensation of 3-acetyl-2,5-dimethyl-thiophene with 3- isopropylidene-diethylsuccinate at the presence of potassium tert -butylate in toluene according to Stobbe reactions and following alcaline hydrolysis of obtained diester, (3) cyclization of 2-[ ⁇ -(2,5-dimethyl-3-thienyl)ethylidene]-3-isopropyliden-succinic acid into cyclic anhydride (fulgide) at the presence a new cyclising agent diethyl chlorophosphate in dry dimethylfomamide, (4) interaction between fulgide and aromatic diamines, (5) cyclization of diamides of 1 , 1 -carbonyldiimidazole in dry
  • a new class of thermally stable photochromic recording media based on bis-fulgimide derivatives and polymer binders namely polycarbonate Or polysterene have been synthesized.
  • the absorption for an initian open form A and a photoinduced cyclic form B as well as kinetic curves for photochemical reactions of coloration and bleaching of these recording media were measured.
  • the experiments of the inventors suggest that synthesized photochromic recording media based on new bis-fulgimides demand to requirements for preparation of recording media and surpass the mono-fylgimide analog on the light-sensitivity value to UV irradiation.
  • the layer within the film can be illuminated from all four sides thereof, thus allowing to reach the required pump beam power density.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optical Record Carriers And Manufacture Thereof (AREA)

Abstract

Composés photochromes constitués essentiellement de deux dithiénylfulgimides hétérocycliques se liant avec des fractions aromatiques ou hétérocycliques se prêtant particulièrement à une utilisation avec des mémoires optiques. Les bis-fulgimides photochromes hétérocycliques préférés sont essentiellement constitués de 2-thiénylfulgimides susceptibles d'être excités par une lumière ultraviolette à la couleur et de modifier l'indice de réfraction. Procédé de préparation de ces bis-fulgimides. Matières photochromes, particulièrement composés photochromes et matrices se prêtant à une utilisation dans des systèmes de mémoire de travail optique, y compris des systèmes de mémoire optiques tridimensionnels pour ordinateurs, applications multimédia et analogues. Plus particulièrement, bis-fulgimides intégrés dans un liant de polycarbonate dont la réversibilité est transformée à partir d'une forme ouverte en une forme cyclique par rayonnement électromagnétique. Système de mémoire optique 3D utilisant un laser à solide à deux longueurs d'ondes.
PCT/CY2005/000003 2004-10-05 2005-10-04 Support d'enregistrement pour memoire operationnel tridimensionnel WO2006037279A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CY0400072A CY2527B1 (fr) 2004-10-05 2004-10-05
CYCY04/00072 2004-10-05

Publications (1)

Publication Number Publication Date
WO2006037279A1 true WO2006037279A1 (fr) 2006-04-13

Family

ID=38729086

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CY2005/000003 WO2006037279A1 (fr) 2004-10-05 2005-10-04 Support d'enregistrement pour memoire operationnel tridimensionnel

Country Status (2)

Country Link
CY (1) CY2527B1 (fr)
WO (1) WO2006037279A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006125317A1 (fr) * 2005-05-25 2006-11-30 Switch Materials Inc. Composes electrochromiques et photochromiques et synthese et utilisation de ceux-ci

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD208689A1 (de) * 1982-07-23 1984-04-04 Hans D Ilge Materialien zur holographischen informationsaufzeichnung
JPS6438063A (en) * 1987-04-30 1989-02-08 Tokuyama Soda Kk Flugimide compound and production thereof
EP0420397A1 (fr) * 1989-07-28 1991-04-03 Wako Pure Chemical Industries Ltd Dérivés de fulgimide
JPH03193761A (ja) * 1989-12-22 1991-08-23 Wako Pure Chem Ind Ltd 新規フルギミド誘導体
EP0900798A1 (fr) * 1996-12-27 1999-03-10 Tokuyama Corporation Composes de fulgimide, utilisation de ces composes et compositions les contenant

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD208689A1 (de) * 1982-07-23 1984-04-04 Hans D Ilge Materialien zur holographischen informationsaufzeichnung
JPS6438063A (en) * 1987-04-30 1989-02-08 Tokuyama Soda Kk Flugimide compound and production thereof
EP0420397A1 (fr) * 1989-07-28 1991-04-03 Wako Pure Chemical Industries Ltd Dérivés de fulgimide
JPH03193761A (ja) * 1989-12-22 1991-08-23 Wako Pure Chem Ind Ltd 新規フルギミド誘導体
EP0900798A1 (fr) * 1996-12-27 1999-03-10 Tokuyama Corporation Composes de fulgimide, utilisation de ces composes et compositions les contenant

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006125317A1 (fr) * 2005-05-25 2006-11-30 Switch Materials Inc. Composes electrochromiques et photochromiques et synthese et utilisation de ceux-ci
US8536205B2 (en) 2005-05-25 2013-09-17 Switch Materials Inc. Photochromic and electrochromic compounds and synthesis and use thereof

Also Published As

Publication number Publication date
CY2527B1 (fr) 2006-05-12

Similar Documents

Publication Publication Date Title
Kawata et al. Three-dimensional optical data storage using photochromic materials
Dvornikov et al. Two-photon three-dimensional optical storage memory
Dvornikov et al. Spectroscopy and kinetics of a molecular memory with nondestructive readout for use in 2D and 3D storage systems
Yanez et al. Photosensitive polymeric materials for two-photon 3D WORM optical data storage systems
JP5157284B2 (ja) 光増感型複合材料及び三次元メモリ材料と記録媒体、光制限材料と素子、光硬化材料と光造形システム、多光子蛍光顕微鏡用蛍光材料と装置
Renge et al. Phthalonaphthalocyanines: new far-red dyes for spectral hole burning
Dvornikov et al. Molecular transformation as a means for 3D optical memory devices
WO2006037279A1 (fr) Support d'enregistrement pour memoire operationnel tridimensionnel
Barachevsky et al. Light-sensitive organic recording media for three-dimensional optical memory
JP5229521B2 (ja) π共役系化合物とその用途、およびそれらを用いた素子、装置
JP2005537954A (ja) マルチスタック光学情報担体
JP5105808B2 (ja) ジスチリルベンゼン誘導体及びこれを用いた三次元メモリ材料、光制限材料、光造形用光硬化樹脂の硬化材料、並びに二光子蛍光顕微鏡用蛍光色素材料。
JPS63149685A (ja) 情報の光学的記録および読み出し方法
JP2002328349A (ja) 光誘起電子移動反応を利用した光応答材料及び光応答素子
JP5339242B2 (ja) 二光子吸収材料とその用途
Stefani et al. Thermochromic fluorophores and their NIR laser induced transformation
CN1329391C (zh) 一种有机光致变色二芳基乙烯化合物及其制备方法与应用
JPH03281386A (ja) 光学記録媒体
JP5578455B2 (ja) π共役系化合物とその用途、およびそれらを用いた素子、装置
JP2013241415A (ja) 二光子吸収材料とその用途
JP5505748B2 (ja) π共役系化合物とその用途、およびそれらを用いた素子、装置
Walker et al. Progress in two-photon 3D optical data storage
Nagamura et al. Materials and devices for ultrafast all-optical processing
JP5047651B2 (ja) 二光子吸収材料とその用途
Barachevsky et al. Organic recording media for 3D bitwise optical memory on optical disks

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KM KP KR KZ LC LK LR LS LT LU LV LY MA MD MG MK MN MW MX MZ NA NG NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SM SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LT LU LV MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase