EP0751925A1 - Substitution electrophile de cristaux liquides discotiques a base de triphenylene - Google Patents

Substitution electrophile de cristaux liquides discotiques a base de triphenylene

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Publication number
EP0751925A1
EP0751925A1 EP95912341A EP95912341A EP0751925A1 EP 0751925 A1 EP0751925 A1 EP 0751925A1 EP 95912341 A EP95912341 A EP 95912341A EP 95912341 A EP95912341 A EP 95912341A EP 0751925 A1 EP0751925 A1 EP 0751925A1
Authority
EP
European Patent Office
Prior art keywords
triphenylene
dichloromethane
mixture
mmol
hexahexyloxytriphenylene
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Withdrawn
Application number
EP95912341A
Other languages
German (de)
English (en)
Inventor
Andrew Neil Cammidge
Richard James Bushby
Neville Boden
Gareth Headdock
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of Leeds
Original Assignee
University of Leeds
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Filing date
Publication date
Application filed by University of Leeds filed Critical University of Leeds
Publication of EP0751925A1 publication Critical patent/EP0751925A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
    • C07B37/04—Substitution
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/94—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C247/00—Compounds containing azido groups
    • C07C247/16—Compounds containing azido groups with azido groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring 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
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • 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
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
    • C09K2019/328—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems containing a triphenylene ring system

Definitions

  • This invention relates to discotic liquid crystals and their synthesis by functionalising and structurally modifying triphenylenes through electrophilic substitution.
  • the invention further relates to these substituted triphenylenes as intermediates or as products in their own right, and to devices incorporating these materials.
  • triphenylene discotic mesogens studied to date are predominantly featureless, and in their pure state are colourless, insulating materials. If discotic liquid crystals are to form the basis of molecular electronic or opto-electronic devices, materials must be prepared which combine suitable mesophase behaviour with the required molecular functionality, i.e. the molecular characteristics required to perform a specific function.
  • Electrophilic substitution of triphenylene cores at ⁇ positions is a way, according to the invention, which allows new properties to be built into a discotic mesogen, e.g. a wider mesophase range, colouring of hitherto uncoloured compounds and insertion of a permanent dipole, the last-named opening up the possibilities of electro-optic switching with a low energy input.
  • a discotic liquid crystal with molecular functionality is synthesised by reacting a low molar mass or polymeric triphenylene derivative with an electrophile, with attack occurring at a positions.
  • the invention provides a triphenylene which is substituted by replacement of a hydrogen atom in an a position and a method of electrophilically substituting a triphenylene in an a position, comprising dissolving the triphenylene in a mixture of semipolar and polar solvents and adding an electrophile or a precursor that in said solvent yields an electrophile, either of which can replace a hydrogen atom at the ⁇ position.
  • the invention extends to the substituted triphenylenes synthesised as set forth above, to those compounds per se, whether or not they are discotic liquid crystals in their own right, to their use as intermediates and to devices incorporating them and discotic liquid crystals derived from them by further reaction of the ⁇ substituent.
  • the product may be a low molar mass or polymeric triphenylene based discotic liquid crystal bearing up to 12 substituents all of which may be the same or some of which may be different and which may be on the ⁇ and/or ⁇ positions of the aromatic nucleus
  • the method according to the invention includes general reactions of the type:
  • E + is an electrophile such as N0 2 + (HNO 3 ), Br + (Br 2 ), R + (RC1), RCO + (RCOC1) or AiCO (ArCOCl) where R is alkyl and Ar is aiyl
  • triphenylene derivatives (which may be highly coloured) can be inco ⁇ orated as solutes into other discotic mesogens (low molar mass or polymeric).
  • the invention includes both physical and chemical inco ⁇ oration of a chromophore into the system, whether as part of a polymer main chain, a side chain off a polymer main backbone, or a side chain off the core (or as the main core itself, as is the case with the monomer form of these materials substituted as set forth above).
  • any other functionality could also have one of these three locations: the main chain, a side chain or the polycyclic core.
  • Such functionality could be, for example, susceptibility to externally applied electric or magnetic fields and inherent redox characteristics such as electron donor/acceptor characteristics which could permit construction of stacked column assemblies.
  • substitution allows new properties to be introduced into the system such as colour (for use in electrooptic displays), conductivity (the redox potentials can be modified to facilitate doping with oxidants and reductants), photoconductivity, a local molecular dipole pe ⁇ endicular to the column axis (dipolar derivatives), non-linear optic properties, and chirality.
  • Some of these induced properties are essential to certain applications of these materials.
  • a "handle" can be substituted into the mesogen for an electric field to switch the whole bulk medium from, for example, a coloured to an opaque state, and for more general bistable systems which consume current only while switching between states.
  • the triphenylene which is used in the method according to the invention may be a hexaether or hexaester of 2,3,6,7,10,11-hexa-hydroxytriphenylene such as hexa-alkoxy or -acyloxy, e.g. hexahexyl (or pentyl or heptyl) oxytriphenylene, (HAT6), a known discotic mesogen whose structural formula is 1 in the reaction scheme below.
  • the 2, 3, 6, 7, 10 and 11 positions are collectively the ⁇ positions, which are all occupied in HAT6, and the (unsubstituted) 1, 4, 5, 8, 9 and 12 positions are collectively the ⁇ positions.
  • the mesophase range of 1 is from 70°C (crystal-mesophase transition) to 100°C ( esophase-isotropic liquid transition).
  • Nitration of HAT6 (1) under mild conditions thus preferably conducted in ether and optionally a carboxylic acid, as will be described more fully, proceeds smoothly to form the mono- ⁇ -nitrated product (2).
  • a further example of ⁇ -nitration is provided by
  • the monochloro compound has an extended mesophase range of (37-98 °C) whereas the mixture of di chloro compounds is a room temperature discotic clearing at 36°C. Both give a single mesophase texture typical of a discotic hexagonal mesophase.
  • the monochloro product can also be obtained using PIFA (phenyliodonium bistrifluoroacetate) followed by tetrabutylammonium chloride..
  • the chloro substituent can be elaborated into an alkyl group as shown.
  • 2,3,6,7,10,11-Hexahexyloxytriphenylene (9.4 g, 11.3 mmol) was dissolved in ether (150 ml) and glacial acetic acid (30 ml). Concentrated nitric acid (3 ml) was added dropwise and the mixture stirred at room temperature for 15 minutes. This use of ether is meritorious and unusual. Normally, a nitration would employ concentrated aqueous H2SO4 to assist the HNO3, and HNO3 would be expected to decompose ether. Ether gives a milder reaction. The solution was washed with water and potassium carbonate solution and the solvent removed m vacuo.
  • the mesophase range of 2 was from below room temperature to 136°C.
  • the inventively synthesised product (2) can be further manipulated, for example as follows: l-Amino-2.3.6.7.10.1 1-hexahexyIoxytriphenylene (3)
  • the product (3) can be manipulated in a variety of ways, of which two are as follows: Azo Derivative of HAT6 (4)
  • the mesophase range of 4 was from about 150°C to 227°C.
  • 1,4,6,7,10,11-Hexahexyloxytriphenylene (0.2 g, 0.24 mmol) was dissolved in ether (15 ml) and acetic acid (6 ml). Concentrated nitric acid (-0.25 ml) was added dropwise and the mixture stirred at room temperature for 20 minutes. The solution was washed with water and potassium carbonate solution and the solvent removed in vacuo. The crude product was purified by column chromatography (silica, dichloromethane/petroleum ether 2:3) and reprecipitated from ethanol to give 1,4,6,7,10,1 l-hexahexyloxy-2-nitrotriphenyIene (11) (0.13 g, 62%) as a yellow solid. Anal. C, 74.0%; H, 9.6%; N, 1.45%; C 5 H 8 3NO 8 requires C, 74.2%, H, 9.6%; N, 1.6%.
  • 2,3,6,7,10,11-Hexahexyloxytriphenylene (1.0 g, 1.2 mmol) was dissolved in dry dichloromethane (45 ml) and cooled to 0°C.
  • PIFA 0.6 g, 1.4 mmol was added and the solution stirred for 5 minutes.
  • Tetra-n-butylammonium chloride (0.67 g, 2.4 mmol) was then added and stirred at 0°C for 10 minutes before being allowed to warm to room temperature. The solution was poured onto methanol and left to stand overnight.
  • the resulting crude solid product was purified by column chromatography (silica, dichloromethane/petroleum ether 1:1) and reprecipitated from ethanol to give 1 -chloro-2,3,6,7, 10, 11 -hexahexyloxytriphenylene (20) (0.45 g, 43%) as a white solid.
  • 2,3,6,7,10,11-hexahexyloxytriphenylene (0.5 g, 0.6 mmol) was stirred in dry THF (20 ml) at -78°C under argon.
  • Butyllithium (1 ml, 1.6 M in hexanes, 1.6 mmol) was added and the solution stirred for 1 hour before adding methyl iodide (0.5 ml). The solution was stirred for a further 2 hours at -78 °C and overnight at room temperature.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Un triphénylène tel que hexyloxytriphénylène hexa-β-substitué est α-substitué par un électrophile dans des cosolvants polaires mélangés, en fonction du processus de réaction illustré par le diagramme (a).
EP95912341A 1994-03-23 1995-03-23 Substitution electrophile de cristaux liquides discotiques a base de triphenylene Withdrawn EP0751925A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB9405793A GB9405793D0 (en) 1994-03-23 1994-03-23 Functionalised discotic liquid crystals mesogens through structural modification of triphenylenes
GB9405793 1994-03-23
PCT/GB1995/000654 WO1995025710A1 (fr) 1994-03-23 1995-03-23 Substitution electrophile de cristaux liquides discotiques a base de triphenylene

Publications (1)

Publication Number Publication Date
EP0751925A1 true EP0751925A1 (fr) 1997-01-08

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EP95912341A Withdrawn EP0751925A1 (fr) 1994-03-23 1995-03-23 Substitution electrophile de cristaux liquides discotiques a base de triphenylene

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EP (1) EP0751925A1 (fr)
GB (2) GB9405793D0 (fr)
WO (1) WO1995025710A1 (fr)

Families Citing this family (5)

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Publication number Priority date Publication date Assignee Title
GB201804511D0 (en) 2018-03-21 2018-05-02 Univ Birmingham Luminescent compounds
GB201804512D0 (en) 2018-03-21 2018-05-02 Univ Birmingham Luminescent compounds
CN111662196A (zh) * 2019-03-09 2020-09-15 四川师范大学 苯并菲盘状液晶化合物及其制备方法
GB201913767D0 (en) 2019-09-24 2019-11-06 Chromatwist Ltd Luminescent compounds
CN112409374B (zh) * 2020-11-20 2022-10-14 四川师范大学 一种刚性核直连的类石墨烯苯并菲盘状液晶的制备方法及介晶性

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3068730D1 (en) * 1979-12-07 1984-08-30 Thomson Csf Mixture of disc-like liquid crystals, electrooptical device using such a mixture and method for the orientation of the molecules in the mixture
GB8823721D0 (en) * 1988-10-10 1988-11-16 Boden N Electronically conducting liquid crystals
EP0703885A1 (fr) * 1993-06-11 1996-04-03 British Technology Group Ltd Synthese de triphenilenes substitues utiles pour les cristaux liquides en forme de disque

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9525710A1 *

Also Published As

Publication number Publication date
WO1995025710A1 (fr) 1995-09-28
GB9405793D0 (en) 1994-05-11
GB2287708A (en) 1995-09-27
GB9505940D0 (en) 1995-05-10

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