WO2008010532A1 - Composé ou sel de celui-ci, procédés destinés à les produire, composés azo aromatiques, et matériau fluorescent - Google Patents

Composé ou sel de celui-ci, procédés destinés à les produire, composés azo aromatiques, et matériau fluorescent Download PDF

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Publication number
WO2008010532A1
WO2008010532A1 PCT/JP2007/064213 JP2007064213W WO2008010532A1 WO 2008010532 A1 WO2008010532 A1 WO 2008010532A1 JP 2007064213 W JP2007064213 W JP 2007064213W WO 2008010532 A1 WO2008010532 A1 WO 2008010532A1
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group
compound
salt
substituent
ring
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PCT/JP2007/064213
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English (en)
Japanese (ja)
Inventor
Naokazu Kano
Junro Yoshino
Akiko Furuta
Takayuki Kawashima
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The University Of Tokyo
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Publication of WO2008010532A1 publication Critical patent/WO2008010532A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1408—Carbocyclic compounds
    • C09K2211/1416—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1408—Carbocyclic compounds
    • C09K2211/1433—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B

Definitions

  • the present invention relates to a compound or a salt thereof and a production method thereof, particularly an aromatic azo compound and a fluorescent material.
  • Fluorescent materials are important as luminescent materials, fluorescent probes, and molecular recognition materials.
  • organic fluorescent substances are disliked because they easily change their properties.
  • tris (8-hydroxyquinoline) aluminum and many other organic molecular force displays are used as light-emitting elements in organic light-emitting diodes (OLEDs) that generate electroluminescence (EL). Yes.
  • OLEDs organic light-emitting diodes
  • EL electroluminescence
  • it is used for biolabeling for detection of dye molecular force proteins such as rhodamine and fluorescein, which are known to have high luminous efficiency.
  • azobenzene which is an aromatic azo compound (azo arene derivative), is one of the most common dye materials.
  • the azo dyes such as Orange II and Congo Red are also azobenzene.
  • azo dyes account for about half of the world's dye production.
  • azabenzene emits little light and does not emit fluorescence.
  • radiative deactivation is sufficiently slow and non-radiative deactivation or photoisomerization proceeds.
  • azobenzene is sometimes used as a photoresponsive molecular switch by taking advantage of the latter property of photoisomerism.
  • catecholborane having an azo group as an intramolecular ligand was synthesized by the present inventors, and the characteristics of a photoresponsive molecular switch by photoisomerism have been reported.
  • Non-Patent Document 1 Photoswitching of the Lewis Acidity of a atecholborane Bearing an Azo Group Based on the Change in Coordination Number of Boron "N. Kano, J. Yoshino, and T. Kawashima, Org. Lett., 7, 3909--3911 (200 5). Disclosure of the invention
  • the present invention has been made in view of the above-described background art, and an object thereof is to provide a fluorescent substance having excellent characteristics.
  • a first aspect of the present invention provides:
  • X and ⁇ may have a substituent, may be condensed, or may be an aromatic ring,
  • the second aspect of the present invention provides
  • X and Y may have a substituent, may be condensed, or may be an aromatic ring, and Ar and Ar are the same F. ]
  • Examples of the aromatic ring include a benzene ring, a condensed benzene ring, thiophene, and a pyridine ring.
  • Examples of the substituent include (0 alkyl group, GO alkoxy group, (m) alkylthio group.
  • dialkylamino group (V) pyrrolidino group, (vi) piperidino group, (vii) morpholino group, (viii) aryl group, (ix) aryloxy group, (X) hydroxy group, (xi) Amino group, (xii) monoalkylamino group, (xiii) acylamino group, (xiv) acyloxy group, (XV) alkylsulfo-lumino group, (xvi) halogen group, (xvii) perfluoroalkyl group, ( xviii) a diarylamino group or hydrogen.
  • (X) hydroxy group, (xi) amino group, (xii) monoalkylamino group, (xiii) acylamino group, (Xiv) acyloxy group, (XV) alkylsulfo-lumino group are protected after deprotection or synthesis. It may be introduced into an aromatic ring by functional group conversion or the like.
  • the substituent has 1 to 22 carbon atoms, or 1 to 6 carbon atoms, an alkyl group having 1, 2, 3, 4, 5 or 6 carbon atoms, carbon atoms 1, 2, 3, 4, 5 or ⁇ .
  • it is an ananoloxy group having 6 or a dialkylamino group having 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon substituents.
  • the third aspect of the present invention provides
  • FIG. 1 is an ORTEP diagram of compound (E) -3a.
  • FIG. 2 (A) Compound (E) -3a absorption spectrum and fluorescence spectrum (excitation at 386 nm) in hexane at room temperature, (B) Compound in an environment irradiated with 360 nm light from the left side ( E) Photo of -3a hexane solution (approx. 5 ⁇ ), (C) Compound in hexane at room temperature ( ⁇ ) -3 c absorption and fluorescence spectra (excitation at 439 nm), (D) It is a photograph of a hexane solution (about 5 ⁇ ) of compound (E) -3c in an environment irradiated with light of 360 nm from the left side.
  • a boron-substituted azobenzene derivative was synthesized by a nucleophilic substitution reaction on a boron reagent with 2-lithioazobenzene. As is apparent from the scheme, this synthesis method is superior to conventional synthesis methods in that it is a one-pot, one-step process.
  • fluorobis (pentafluorophenyl) borane (2a) was prepared.
  • n-butyllithium (1.10 equivalent) and fluorobis (pentafluorophenol) in ether at -112 ° C Borane (2a) (l.10 equivalents) was reacted sequentially to produce bis (pentafluorophenyl) [2- (phenylazo) phenyl] borane ((E) -3a) in air at a yield of 28%. Synthesized as a stable brown solid.
  • [2- (4-methoxyphenol) phenol] bis (pentafluorophenol) borane ((E) -3c) is also (E) -2-iodo-4'- Synthesized from methoxyazobenzene ((E) -4) and compound (E) -2a in 27% yield.
  • compound (E) -3a-c is a 4-coordinate boron compound. Each region showed a broad peak, indicating that compound (E) -3a_c is a tetracoordinate boron compound in solution.
  • FIG. 1 is an ORTEP diagram of compound (E) -3a.
  • the crystal structure of Compound (E) -3a was determined by X-ray crystal structure analysis.
  • the bond length of the N2-B1 coordination bond is a BN bond length that forms a five-membered ring. So far, the range of data stored in the Cambridge Strucctural Database is 1.625-1.842 A. It is one of the shortest categories.
  • N1-N2 bond length [1.2704 (18) A] is almost the same as the average value (1.25A) of (E) -azobenzene derivatives reported in the past. Talking.
  • the bond length (A) and bond angle (deg) were also as follows. Nl— N2, 1.2704 (18); B1-N2, 1.625 (2); Bl— C 1, 1.599 (2); Bl— C 13, 1.62 9 (2); B1-C 19, 1.627 (2); C I- Bl- C 13, 117.74 (13); C I- Bl- C 19, 106.04 (13); C 13-B1-C 19, 117.93 (13); CI— Bl— N2, 95.53 (12); C 13— Bl— N2, 105.07 (12); C 19 -B1-N2, 112.35 (13).
  • Figure 2 shows (A) the absorption spectrum and fluorescence spectrum of compound (E) -3a in hexane at room temperature (excitation at 386), (B) environment irradiated with light of 360 nm from the left side. Photo of compound)-3a in hexane (approximately 5 ⁇ ), (C) absorption spectrum and fluorescence spectrum of compound ( ⁇ ) -3 c in hexane at room temperature (excitation at 439 nm), (D) It is a photograph of a hexane solution (about 5 ⁇ ) of compound (E) -3c in an environment irradiated with light of 360 nm from the left side.
  • the fluorescence quantum yield refers to the number of photons emitted Z, the number of photons absorbed, and is a value representing how much light is emitted as fluorescence when 1 light is applied. The larger this value is, the stronger and more fluorescent.
  • the azobenzene compound (E) -3c also showed strong green fluorescence as with (E) -3a when irradiated with light. In the fluorescence spectrum in hexane, Compound (E) -3c showed an emission maximum at 524 ⁇ m when excited at 439 nm. The fluorescence quantum yield ⁇ of (E) -3c at room temperature in hexane was determined to be 0.76. This value is the highest ever for an azobenzene derivative.
  • the fluorescence quantum yield ⁇ of compound (E) -3b excited at 370 nm was 0.01 or less. Considering that there is a main peak at the short wavelength corresponding to the transition of the aryl group, which has almost no peak at the wavelength based on the ⁇ - ⁇ * transition in the excitation spectrum, the emission of compound (E) -3b It is considered that the light emission from the aryl group bonded to the boron is not the light emission of.
  • the (E) -3a 1 ( ⁇ , ⁇ *) excited state is at a lower level than the ⁇ *) excited state. 11, ⁇ *) and ⁇ , ⁇ *) level energy level inversion increases the probability of transition from the excited state to the ground state based on the orbital symmetry. This reversal phenomenon is considered to be one of the reasons that protonated azobenzen 4- (dialkylamino) azobenzene emits fluorescence.
  • the energy level of the occupied orbitals of the aryl groups bonded to boron in (E) -3b is relatively high, and the ⁇ orbitals of the azo groups cannot occupy HOMO, so the fluorescence quantum yield is extremely low. It will be suppressed. Therefore, the characteristic emission characteristics of (E) -3a and (E) -3c are: 1 ( ⁇ , ⁇ *) and 1 ( ⁇ , ⁇ *) level inversion and strong !, electron withdrawing The lowest singlet excited state due to the low energy level of the occupied CF orbital group
  • the absolute value of the fluorescence quantum yield can be obtained by assuming that the quantum yield of fluorescein (0.1M NaOH aqueous solution) is 0.85 9,10-diphenylanthracene (cyclohexane solution) and that the quantum yield is 1.00.
  • the quantum yield of anthracene (cyclohexane solution) was determined as 1.00 and excited at 440 nm and excited at 439 nm.
  • Substituents are not limited to n-Bu (0 alkyl group, GO alkoxy group, (iii) alkylthio group, (iv) dialkylamino group, (V) pyrrolidino group, (vi) piperidino group, (vii) Morpholino group, (viii) aryl group, (ix) aryloxy group, (X) hydroxy group, (xi) amino group, (xii) monoalkylamino group, (xiii) acylamino group, (xiv) acyloxy group, (XV) It may be an alkylsulfo-lumino group, (xvi) a halogen group, (xvii) a perfluoroalkyl group, (xviii) a diarylamino group or hydrogen, etc.
  • the substituent group has 122, more preferably 16 carbon atoms.
  • An alkyl group having 1 2 3 4 5 or 6 carbon atoms, an alkoxy group having 1 2 3 4 5 or 6 carbon atoms, or a carbon atom Preferably, it is a dialkylamino group having 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon substituents.
  • Azobenzene is one of the most common pigment materials, and accounts for about half of the world's total dye production when viewed as an application as an azo dye. In general, azobenzene does not emit light. However, in the case of compounds having the above-mentioned luminescent properties, the usefulness of fluorescent light can be reduced due to the diversity of the synthesis method and the ease of adjustment of the fluorescence wavelength. The above embodiment is epoch-making in that it is expected to become a material.
  • the compound of this embodiment can also be used as a fluorescent paint or fluorescent dye. Since the compound of this embodiment has high brightness even in a small amount, it is excellent as a material for fluorescent paints and fluorescent dyes. It can also be used as a fluorescent ink. If used as a translucent fluorescent ink, it can also be applied to fluorescent pens. Because it is translucent, it can be widely used as a writing instrument for checking because it is easy to read overprinted characters and immediately become noticeable with a fluorescent color. In addition, fluorescent dyes can be added to white clothing and laundry detergents for the purpose of whitening by fluorescence, and dyes that emit colorless and blue fluorescence in visible light have the effect of hiding the yellowing of paper and cloth. Therefore, it can also be used as a fluorescent brightening agent.
  • Fluorescent labeling agents for biological materials fluorescent probes (cell detection, DNA detection, protein detection), and clinical diagnosis, which are often required to have high sensitivity, may be considered.
  • the compound of this embodiment is suitable for a technique of coloring a specific biological tissue, cell, organelle, etc. with a special dye, and for staining.
  • a staining agent or staining agent the property that a specific dye binds strongly to characteristic biomolecules (proteins, nucleic acids, lipids, hydrocarbons, etc.) contained in the specimen to be observed Even if it uses Even a substrate that reacts with the element to develop color may be used.
  • the target is used as a derivative of the present embodiment that emits fluorescence when performing microanalysis using HPLC or the like. Conversion and analysis can be ignored.
  • a device used for flow cytometry which is a technique for dispersing fine particles in a fluid, flowing the fluid finely, and optically analyzing individual particles. It is also possible to employ the compound of the present embodiment in certain flow cytometers. Similarly, fine particles can be selectively recovered.
  • An example of this principle is as follows. Apply light of a certain wavelength (eg laser light) to the fluid.
  • Forward Scatter forward scattering in the direction along the ray
  • Side Scatter side scattering in the direction perpendicular to the ray
  • fluorescence detectors are provided for detecting the fluorescence generated by the laser light by labeling the fine particles with a fluorescent substance. These detectors detect the light and fluorescence affected by the particles in the fluid.
  • the compound of this embodiment is also conceivable to apply the compound of this embodiment as a light-emitting element of organic electroluminescence (organic EL, organic light emitting diode, OLED).
  • organic EL organic light emitting diode
  • OLED organic light emitting diode
  • the fluorescent material is applied to organic electoluminescence, it is desirable that the fluorescent material has a high quantum yield in order to obtain high luminance with low energy (low power). This is advantageous.
  • the compound of this embodiment to a cathode ray tube.
  • electrons are focused on a single electron beam, deflected by a magnetic field, scanned on a display surface (anode, anode) coated with a fluorescent material, and light is emitted when the electrons collide with the fluorescent material. Is done.
  • FED field emission display
  • the emitted electrons are pulled to the anode side on the anode side, and light is emitted by colliding the electrons with the phosphor on the anode side.
  • the compound of the present embodiment it is also conceivable to apply the compound of the present embodiment to a fluorescent lamp.
  • a material that absorbs ultraviolet rays emitted from mercury and emits visible light as fluorescence is applied to the surface of the low-pressure mercury lamp.
  • the compound of the present embodiment to a cold cathode tube and a light source for a liquid crystal backlight.
  • the types of fluorescent lamps include, for example, general fluorescent lamps, straight tubes, rod-shaped fluorescent lamps, ring-shaped fluorescent lamps, donut-shaped fluorescent lamps, slim type, twin type, ring-shaped fluorescent lamps, bulb-type fluorescent lamps, compact fluorescent lamps , High-frequency lighting-only fluorescent lamps, cold cathode fluorescent lamps (cold cathode fluorescent lamps), long-time afterglow fluorescent lamps, fluorescent lamps with photocatalyst film, synthetic resin-coated fluorescent lamps, electrodeless fluorescent lamps, and fluorescent lamps for insects , Fluorescent lamps for insect repellent, and those with small metal balls.
  • azobenzene derivatives as photochromic dyes.
  • Applications such as the control of host-guest chemistry with azobenzene derivatives, the control of polymer and film properties with azobenzene, the control of liquid crystal properties with azobenzene, and the combination of photochromism and electrochemistry of azobenzene.
  • the bond between boron and nitrogen is cleaved, so that it has properties as a general azobenzene derivative, and light is emitted from the phosphor. It can be disregarded to change to a responsive molecular switch.
  • azobenzenes are not used as light-emitting moieties, but there are some known azobenzene derivatives that are exceptionally fluorescent. Protonated azobenzene, hydroxyazobenzene, aminoazobenzene, etc. are examples of azobenzene derivatives that exhibit fluorescence. Can be mentioned. Many of the azobenzene derivatives exhibiting fluorescence exhibit fluorescence only in a low temperature matrix, and the fluorescence quantum yield is extremely low.
  • an azobenzene derivative having high emission characteristics and high fluorescence quantum yield can be synthesized, so that the possibility of application as a fluorescent probe of a chemical sensor or a light-emitting element is expected to greatly expand. Is done.
  • fluorescence can be observed at a high temperature including room temperature and in a wide temperature range.
  • factors that determine the intensity of fluorescence include the intensity of light hitting a substance, the thickness of the substance, the molar concentration of the substance, and the fluorescence quantum yield of the substance.
  • the fluorescence quantum yield of a substance is a property unique to the substance, and in reality, a substance with a high fluorescence quantum yield has a lot of power.
  • a substance having a high fluorescence quantum yield (Ich compound) is applied to the material, it must be easy to synthesize, have multiple synthesis methods, and have a simple structure. It is desirable to satisfy the requirements such as the ability to synthesize various derivatives and the existence of many studies on the relationship between structure and properties. Also in this point, the aromatic azo compound of the above-described embodiment is excellent.
  • the azabenzene derivative of the above-described embodiment emits fluorescence not only when it is made into a solution but also when it is applied in a thin film form. As a result, a film-like phosphor can be easily obtained, so that the use of the azobenzene derivative of the above-described embodiment is great. Ki

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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Abstract

L'invention concerne une série de composés azo aromatiques (dérivé d'azoarène) possédant un rendement quantique de fluorescence élevée. Plus particulièrement, elle concerne du [2-(4-méthoxyphénylazo)phényl]bis(pentafluorophényl)borane, qui consiste en un dérivé d'azobenzène, à rendement quantique de fluorescence dans une solution à température de laboratoire de 0,76, qui fut le plus élevé historiquement. Diverses investigations sur les dérivés d'azobenzène ont été réalisées et de nombreuses techniques de synthèse mises au point. L'invention concerne également un matériau fluorescent utile parce qu'il conserve intactes la variété et la simplicité des procédés de synthèse du dérivé d'azobenzène et qu'il facilite la régulation des longueurs d'onde de fluorescence, etc. Les composés de l'invention possèdent d'excellentes propriétés et peuvent, par ailleurs, être utilisés dans diverses applications.
PCT/JP2007/064213 2006-07-19 2007-07-18 Composé ou sel de celui-ci, procédés destinés à les produire, composés azo aromatiques, et matériau fluorescent WO2008010532A1 (fr)

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JP2006197511A JP2009234915A (ja) 2006-07-19 2006-07-19 化合物又はその塩、それらの製造方法、芳香族アゾ化合物及び蛍光材料

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JP2014202957A (ja) * 2013-04-05 2014-10-27 浜松ホトニクス株式会社 光学モジュールおよび観察装置
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US10175552B2 (en) 2013-04-05 2019-01-08 Hamamatsu Photonics K.K. Optical module, optical observation device, and light exposure device
CN111398468A (zh) * 2020-04-08 2020-07-10 广州市食品检验所（广州市酒类检测中心） 食品中偶氮工业染料的高分辨质谱非定向筛查检测方法
CN112796007A (zh) * 2021-01-23 2021-05-14 北京印刷学院 氢键/溴键协同组装溴键偶氮吡啶/量子点发光纤维及其制备方法

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JP2017138340A (ja) * 2017-05-22 2017-08-10 セイコーエプソン株式会社 検出装置

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014202957A (ja) * 2013-04-05 2014-10-27 浜松ホトニクス株式会社 光学モジュールおよび観察装置
US9784980B2 (en) 2013-04-05 2017-10-10 Hamamatsu Photonics K.K. Optical module and light exposure device
US10175552B2 (en) 2013-04-05 2019-01-08 Hamamatsu Photonics K.K. Optical module, optical observation device, and light exposure device
US10495896B2 (en) 2013-04-05 2019-12-03 Hamamatsu Photonics K.K. Optical module and observation device
CN111398468A (zh) * 2020-04-08 2020-07-10 广州市食品检验所（广州市酒类检测中心） 食品中偶氮工业染料的高分辨质谱非定向筛查检测方法
CN111398468B (zh) * 2020-04-08 2022-09-20 广州市食品检验所（广州市酒类检测中心） 食品中偶氮工业染料的高分辨质谱非定向筛查检测方法
CN112796007A (zh) * 2021-01-23 2021-05-14 北京印刷学院 氢键/溴键协同组装溴键偶氮吡啶/量子点发光纤维及其制备方法

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