EP2334630A2 - Carbonyl derivatives having a c3 symmetry, their preparation and uses thereof - Google Patents
Carbonyl derivatives having a c3 symmetry, their preparation and uses thereofInfo
- Publication number
- EP2334630A2 EP2334630A2 EP09760016A EP09760016A EP2334630A2 EP 2334630 A2 EP2334630 A2 EP 2334630A2 EP 09760016 A EP09760016 A EP 09760016A EP 09760016 A EP09760016 A EP 09760016A EP 2334630 A2 EP2334630 A2 EP 2334630A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- radical
- substituted
- anions
- organic
- possibly
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
- C07C49/675—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having three rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/788—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic with keto groups bound to a condensed ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
- C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
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- 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
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Definitions
- the present invention relates to carbonyl derivatives of benzene having a C3 symmetry and of the general formula (I).
- the invention also relates to the method for synthesizing said compounds and to their use in particular as components of matrices in the molecular electronics, spintronics and telecom fields.
- the components for molecular electronics are very complex and their functioning is based on the combined action of a plurality of components and materials.
- the layers which can be interposed in between the cathode and the anode in a OLED device are as follows: a layer containing a material suitable for generating positive charges or holes (Hole Injection Material, HIM), a layer containing a material for transporting holes or positive charges (Hole Transport Material, HTM), a layer for emitting fluorescent or phosphorescent light.
- HIM Hole Injection Material
- HTM Hole Transport Material
- Such a layer may in turn be made of a plurality of layers containing a material which blocks the electrons (Electron Blocking Material, EBM), a material which emits light (Light Emitting Material, LEM), a material which blocks the holes (Hole Blocking Material, HBM), a layer which contains a material which transports the electrons (Electron Transport Material, ETM).
- EBM Electrode Blocking Material
- LEM Light Emitting Material
- HBM Hole Blocking Material
- ETM Electrode Blocking Material
- the electron flow goes from cathode to anode.
- the materials layered onto the layers may in turn comprise single organic compounds or mixtures of different compounds similar in their nature to each other and which may have the same functions within the layer. From what has been described above, it can be gathered how complex the electronic devices available on the market can be, and how much it is felt the need for having a large range of organic compounds available.
- C3 symmetry it is meant a molecular structure which shows a ternary symmetry axis, i.e., that a 120 degrees rotation around the axis which is perpendicular to the plane, in this case benzene, and which passes through its center, can reproduce the molecule itself.
- 1,3,5-substituted benzene is known for some of the applications herein claimed (Yamaguchi, Yoshihiro; Ochi, Takanori; Miyamura, Satoshi; Tanaka, Takahiro; Kobayashi, Shigeya; Wakamiya, Tateaki; Matsubara, Yoshio; Yoshida, Zen-ichi. Journal of the American Chemical Society (2006), 128(14), 4504-4505), but none of the compounds described in what follows can be found in the Prior Art.
- the patent application WO2007/137725 describes compounds characterized by the presence of substituents in the position Y on the Ar.
- the compounds herein claimed do not show such a well characterized substitution.
- they are particularly suitable, differing in that from the compounds described in WO2007/137725, to yield radical-anions (and radical cations) with a reversible electrochemical behaviour.
- Carbonyl derivatives of different types are described in Pigge F. C. et al., Tetrahedron Letters, 42, no. 47, (2001), 8259-8261; Pigge F.C. et al., Tetrahedron Letters, 41, no. 34, (2000), 6545-6549; Pigge F.C. et al., J. Org. Chem., 73, no. 7, (2008), 2760-2767. These compounds are not suitable for the applications mentioned above because of their unsuitable reduction and/or oxidation potentials (E°ox, E°red).
- Carbonyl derivatives of benzene with C3 symmetry have now been found which show interesting chemical-physical features in particular for use in the molecular electronics, spintronics and telecom fields, in particular E°red, such to make easier for the molecule to form the radical-anion.
- Such derivatives are characterized by having all the substituents which are identical to each other.
- A is a group chosen from among the radicals of: biphenylene, carbazole, fluoranthene, fluorene, dibenzothiofene, dibenzofurane, fluorenone, bifluorenylidene, triphenylene, cyclooctatetraene (COT), dibenzocyclooctatetraene (DBCOT), coronene, acenaphtylene, triptycene, azulene, benzo(ghi)fluoranthene, 2-phenyl-l,3,4-oxadiazole, anthracene; with the proviso that the A group does not have arylamine-type and Y-type substituents, with Y having the following core, possibly substituted: wherein E is C, a heteroatom chosen from among O, S,
- N, P, possibly substituted, or a single link N, P, possibly substituted, or a single link.
- R and Ar are alkyl and aryl respectively and have the meaning indicated herein below.
- radical-anions and radical- cations in particular mono-, di- and tri-anions and mono-, di- and tri- cations corresponding to the compounds of formula (I).
- radical- anions it is meant the chemical species which is obtained by addition of one electron to the corresponding neutral species and, consequently, by radical-cations the chemical species obtained by subtraction of one electron from the corresponding neutral species.
- a further object of the invention are the method for synthesizing the compounds of formula (I) and the method for synthesizing their corresponding radical-anions and/or radical-cations, alone or in a mixture thereof. Still a further object of the invention are the compositions comprising the compounds of formula (I) and/or their corresponding radical-anions and/or radical-cations, alone or in a mixture thereof to be employed in the manufacture of electronic components.
- Still a further object of the invention are the electronic devices which contain the compounds of formula (I) of the invention and/or the corresponding radical anions and/or radical-cations, alone or in a mixture thereof.
- Still a further object of the invention is the use of the compounds of formula (I) and/or of their corresponding radical anions and/or radical- cations, alone or in a mixture thereof, for the manufacture of molecular electronics components, in particular as electron transport compounds in ETM materials.
- radical-anion a chemical species which has the ability to take an electron while keeping its negative charge and its radical feature is meant.
- a compound which is deprived of one electron, bearing onto it a positive charge is called radical-cation.
- the radical-anion and radical-cation species may be obtained by chemical or electrochemical route ["Organic Electrochemistry", 4a Ed., Henning Lund & Ole Hammerich Eds., Marcel Dekker Inc, New York (2001) and “Electrochemical methods", 2a Ed., A.J. Bard, L.R. Faulkner, Wiley, New York (2001)].
- a radical-anion has a reversible behaviour when, by inverting the potential sign applied to a suitable value, it yields back the starting compounds (see examples reported in the technical literature cited above). The same is true with the radical-cation.
- One of the fundamental layers in an electronic device which uses the compounds according to the invention is the one relating to the electron transport.
- the material to be layered in this layer should thus be able to easily take up electrons yielding the radical-anions of the molecules involved.
- the compound in its neutral form must have the feature to form good amorphous films with elevated Tg to favour a stable operating condition inside the electronic device in the long run, when used.
- the compounds of formula (I) of the present invention are characterized in that the energetic levels which can be obtained are particularly suitable for the claimed applications, especially if referred to taking up of electrons, photoemission, and to solubility in organic solvents in case of amide groups-containing molecules.
- the molecule is characterized by an high degree of symmetry, being all the A substituents identical to each other.
- biphenylene a molecular structure of the formula (II) is meant; by the term carbazole a molecular structure of the formula (III) is meant; by the term fluoranthene a molecular structure of the formula (IV) is meant; by the term fluorene a molecular structure of the formula (V) is meant; by the term dibenzothiophene a molecular structure of the formula (VI) is meant; by the term dibenzofurane a molecular structure of the formula (VII) is meant; by the term fluorenone a molecular structure of the formula (VIII) is meant; by the term bifluorenylidene a molecular structure of the formula (IX) is meant; by the term triphenylene a molecular structure of the formula (X) is meant; by the term cyclooctatetraene a molecular structure of the formula (XI) is meant; by the term dibenzocycloo
- All the structures shown above may have more than one possible binding position to the central benzentricarbonyl core, some more likely than others by the chemical point of view.
- A is: carbazole radical, N-alkyl substituted carbazole (i.e., with an alkyl bound to the N atom), N-phenyl substituted carbazole (i.e., with a phenyl bound to the N atom), N-CN substituted carbazole (i.e., with a cyano group bound to the N atom), C-alkyl substituted carbazole (i.e., with an alkyl bound to the C atom), C-OH substituted carbazole (i.e., with a hydroxyl group bound to the C atom), C-SH substituted carbazole (i.e., with a thiol group bound to the C atom), C-halogen substituted carbazole (i.e., with a halogen bound to the C atom), C-CN substituted carbazole (i.e., with a cyano group bound to the C atom), biphenylene radical, alkyl substituted bi
- the compounds of the invention can be easily synthesized by means of the Friedel Crafts reaction using e.g. AICI3 as the catalyst or equivalent catalysts. Such reactions are known to the expert in the art and can be carried out starting from compounds which are easily available on the market or are easily synthesized.
- a method to synthesize the compounds of the invention comprises the following steps:
- a solvent preferably an organic sulphide, such as carbon sulphide, together with a stychiometric quantity (e.g., in a 3:1 ratio) of a Lewis acid, preferably aluminium trichloride at a temperature not above 15-20 0 C, preferably in a water/ice bath;
- radical-anions of the compounds of the invention can be obtained, preferably by a chemical or an electrochemical route, by adding an electron to the corresponding neutral compound; particularly preferred is the electrochemical route because of its selectivity and ease in carrying it out.
- di-anion and tri-anion radicals which can be paramagnetic species, it is sufficient to operate at more negative potentials with respect to those used to obtain the corresponding mono- or di-anions, indicated in the experimental conditions.
- the molecular structure of the compounds of the invention shows chemical-physical features which are mainly linked to the molecular symmetry class and are particularly interesting for the use in the molecular electronics, spintronics and telecom fields.
- the compounds herein described can be used as monomers for the synthesis of oligomers and polymers useful for the applications described above.
- the compounds of the invention can find application as coatings or thin films on suitable supports (metal or non-metal) by means of known techniques (chemical, chemical-physical, physical) known to the expert in the art.
- the electronic devices which incorporate them and/or onto which they are layered carry at least one active layer which comprises at least one compound of the invention, preferably mixtures, possibly comprising radical-anions and/or radical-cations, layered onto said supports.
- the compounds can be layered onto the supports of electronic devices by means of sublimation or with deposition techniques in vapour phase (e.g., OVPD-organic vapour phase deposition) or by means of spin- coating or with printing techniques such as offset or ink-jet (all of which are techniques known to the expert in the field).
- deposition techniques in vapour phase e.g., OVPD-organic vapour phase deposition
- spin- coating e.g., OVPD-organic vapour phase deposition
- printing techniques such as offset or ink-jet (all of which are techniques known to the expert in the field).
- spintronics With the general term of spintronics the technical field wherein organic molecular species can be used using the spin properties of electrons which are present in the molecule.
- the information is transmitted and stocked by the electricity flow in the form of subatomic particles negatively charged, called electrons, or positively charged, called holes.
- the zero and one of the binary code of a computer are represented by the presence or absence of electrons in a semiconductor or other material.
- the information is stocked and transmitted by using a different property of electrons, i.e., their spin.
- aromatic compounds derivatives are among those classes of molecules which can be used instead of inorganic species, mostly in ways which are related to their organic molecular structure, in the arrangement and manufacture of electronic devices.
- the compounds mentioned above can be used (non comprehensive list) for the components of: OLEDS, organic semiconductors, field-effect transistors (OFETS), molecular rectifiers, organic molecules for laser applications, organic photovoltaic devices, organic spin valves, solar cells, electrochromic and thermochromic materials, in general for electronic components and devices on a molecular scale, components and devices for gaseous H2 sensors, components and devices for the manufacture, transmission and detection of electromagnetic frequencies also in the field of far infra-red, components and devices for spintronics, for chemical sensors, and for the industrial manufacture of metamaterials in general, useful for the above mentioned applications.
- the compounds claimed in the present patent application can be useful as materials which transport negative charges (electrons) or positive charges (holes) or as guest materials in electronic devices. It is therefore claimed the use of the compounds herein described in electronic devices (e.g., OLEDS), i.e., devices for light-emitting diodes based on organic compounds, in particular emitting in the visible, in the blue and green-blue and emitting white light (nowadays used also in television screens), in the OFETS, i.e., field-effect transistors based on organic compounds, integrated circuits based on organic compounds, solar cells based on organic compounds, light-emitting transistors based on organic compounds, light-emitting electrochemical cells, organic photoreceptors and organic laser-diodes, electrochromic materials, organic spin valves, gaseous H2 sensors.
- OLEDS organic light-emitting diodes based on organic compounds, in particular emitting in the visible, in the blue and green-blue and emitting white light (nowa
- the compounds herein claimed can therefore be used as active means in electroluminescent devices (lasers included) or photovoltaic devices and as materials carrying charges in electroluminescent devices, transistors, photovoltaic devices, in telecom devices, i.e., for the manufacture, transmission and detection of electromagnetic frequencies, and in general for the industrial manufacture of metamaterials useful for the above mentioned applications.
- the compounds herein described can be used in combination with others as additional species in the manufacture of the above mentioned applications.
- Example 1 Synthesis of benzene-l,3,5-tri-[3-carbonyl-(N-ethyl-)- carbazolel (BTCEC)
- reaction is left to come down to room temperature. It is then refluxed and is kept under agitation for further 2 hours.
- Example 5 Synthesis of TAMPOE - (Nl,N3,N5-trietyl-Nl,N3,N5- tris(5-(4-methoxyphenyl)-l,3,4-oxadiazol-2-yDbenzene-l,3,5- tricarboxamide) .
- the mixture is stirred at room temperature and is followed by TLC until the starting compound (ca. 2-3 h) is used up, it is mixed with water (10 ml) and extracted with 10 ml of CH2CI2.
- radical anions of the compounds of the invention are preferably obtained by the chemical or the electrochemical route by means of addition of an electron to the corresponding neutral compound; particularly preferred is the electrochemical route due to its selectivity and ease of execution.
- This method is carried out using an electrochemical cell comprising two sections: an anodic and a cathodic one; in the cathodic one a working electrode and a reference calomel electrode are placed.
- An aprotic solvent or mixtures of: typically N,N-dimethylformamide, acetonitrile, tetrahydrofuran, N-methylpyrrolidone, dimethyl sulphoxide, preferably N,N-dimethyl formamide, acetonitrile and, particularly preferred N,N- dimethylformamide, is made anhydrous according to the current procedures, and to it a supporting electrolyte, typically tetraethylammonium perchloride, tetrabutylammonium tetrafluoroborate, lithium perchlorate, particularly preferred is tetraethylammonium perchloride, also made anhydrous, is added so that a concentration comprised in between IM and 0.01 M, preferably 0.2M and 0.05
- the electrolyte solution thus prepared is placed in the cathodic section which is separated from the anodic one by a portion of the same electrolyte solution conveniently gelified and wherein the anode is placed (Pt net).
- the selected compound is added to the electrolyte solution present in the cathodic section of a divided cell, under nitrogen flux, so that a concentration comprised in between 0.01 M and 1 mM, preferably comprised in between 0.01 M and 0.5 mM, and particularly preferred 1 mM is obtained.
- a reticulated vitreous carbon electrode (RVC) as the cathode and a calomel electrode (SCE) as the reference electrode are placed in the cathodic section of the cell.
- an electrode preferably a platinum gauze electrode
- Other electrode materials which can be used to make the working electrodes are: mercury, lead, silver, composite materials based on Ti, conducting carbon materials, carbon-containing conducting materials, chemically modified electrodes, particularly preferred is vitreous carbon due to the following features: wide electrochemical window, low cost, absence of toxicity and ease of use.
- the supporting electrolytes which can be used are those which preferably contain: perchloride anions, tetrafluoroborate anions, hexafluorophosphate anions, lithium cations, sodium cations, tetraalkylammonium cations and mixtures thereof; particularly preferred are the perchloride anions and the tetraethylammonium cations.
- a convenient voltage is applied in between the electrodes so that the desidered radical-anion is obtained, usually a voltage about 0.2 V more negative than the standard potential E° of the compound to be treated (vs SCE).
- the working temperatures can be comprised in between -2O 0 C and +50 0 C; particularly preferred is room temperature.
- An example of radical anions mono-, di-, tri-, anions is shown in the experimental part and their relative E c p /E° are expressed in the following Table 1 and 2. Table 1
- E c p i, E C P 2, E C P 3 represent, respectively, the peak potentials detected in the voltammetries and relative to one electron, two electrons and three electrons reception for the compounds indicated. * Saturated Calomel Electrode.
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Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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ITRM2008A000523A IT1391474B1 (en) | 2008-10-02 | 2008-10-02 | CARBONYL DERIVATIVES AT C3 SYMMETRY, THEIR PREPARATION AND THEIR USE |
PCT/IT2009/000449 WO2010038252A2 (en) | 2008-10-02 | 2009-10-02 | Carbonyl derivatives having a c3 symmetry, their preparation and uses thereof |
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EP2334630A2 true EP2334630A2 (en) | 2011-06-22 |
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EP09760016A Withdrawn EP2334630A2 (en) | 2008-10-02 | 2009-10-02 | Carbonyl derivatives having a c3 symmetry, their preparation and uses thereof |
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IT (1) | IT1391474B1 (en) |
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CN103922915B (en) * | 2014-04-14 | 2016-05-11 | 国家纳米科学中心 | A kind of two pyrene compounds, preparation method and application thereof with piezallochromy character |
US9475777B2 (en) * | 2014-05-16 | 2016-10-25 | University Of Houston System | Thermally robust, highly porous, and partially fluorinated organic framework with affinity for hydrocarbons, fluorocarbons and freons |
EP3275865A1 (en) * | 2016-07-29 | 2018-01-31 | Ludwig-Maximilians-Universität München | Amide-based hole-transporting or hole-injecting materials |
US11158809B2 (en) | 2017-10-31 | 2021-10-26 | Samsung Display Co., Ltd. | Light absorber and organic electroluminescence device including the same |
KR101981294B1 (en) | 2017-10-31 | 2019-05-23 | 삼성디스플레이 주식회사 | Light absorber and organic electroluminescence device including the same |
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AU8889101A (en) * | 2000-09-07 | 2002-03-22 | Telik Inc | Benzene tricarboxylic acid derivatives as insulin receptor activators |
ITRM20040352A1 (en) * | 2004-07-15 | 2004-10-15 | Univ Roma La Sapienza | OLIGOMERIC DERIVATIVES OF SPIROBIFLUORENE, THEIR PREPARATION AND THEIR USE. |
DE102006025777A1 (en) * | 2006-05-31 | 2007-12-06 | Merck Patent Gmbh | New materials for organic electroluminescent devices |
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2008
- 2008-10-02 IT ITRM2008A000523A patent/IT1391474B1/en active
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2009
- 2009-10-02 EP EP09760016A patent/EP2334630A2/en not_active Withdrawn
- 2009-10-02 WO PCT/IT2009/000449 patent/WO2010038252A2/en active Application Filing
Non-Patent Citations (1)
Title |
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Also Published As
Publication number | Publication date |
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ITRM20080523A1 (en) | 2010-04-03 |
WO2010038252A2 (en) | 2010-04-08 |
WO2010038252A3 (en) | 2010-05-27 |
IT1391474B1 (en) | 2011-12-23 |
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