GB2579298A - Conductive polymers - Google Patents

Conductive polymers Download PDF

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GB2579298A
GB2579298A GB2001560.8A GB202001560A GB2579298A GB 2579298 A GB2579298 A GB 2579298A GB 202001560 A GB202001560 A GB 202001560A GB 2579298 A GB2579298 A GB 2579298A
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polymer according
moieties
optionally
polymer
independently
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GB202001560D0 (en
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George Wildgoose Gregory
Edward Ashley Andrew
M Courtney James
J Lawrence Elliot
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UEA Enterprises Ltd
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UEA Enterprises Ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/124—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
    • C08G79/08—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing boron
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
    • H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES OR LIGHT-SENSITIVE DEVICES, OF THE ELECTROLYTIC TYPE
    • H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
    • H01G11/04—Hybrid capacitors
    • H01G11/06—Hybrid capacitors with one of the electrodes allowing ions to be reversibly doped thereinto, e.g. lithium ion capacitors [LIC]
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES OR LIGHT-SENSITIVE DEVICES, OF THE ELECTROLYTIC TYPE
    • H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
    • H01G11/22—Electrodes
    • H01G11/30—Electrodes characterised by their material
    • H01G11/48—Conductive polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/147—Side-chains with other heteroatoms in the side-chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/148—Side-chains having aromatic units
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3221—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more nitrogen atoms as the only heteroatom, e.g. pyrrole, pyridine or triazole
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/40—Polymerisation processes
    • C08G2261/44—Electrochemical polymerisation, i.e. oxidative or reductive coupling

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Power Engineering (AREA)
  • Medicinal Chemistry (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

Abstract

Disclosed herein is a polymer comprising a conductive backbone having a plurality of Lewis pair side chain moieties thereon. Said Lewis pair side chain moieties each comprise a Lewis acid moiety (LA) comprising an electron pair acceptor, and a Lewis base moiety (LB) comprising an electron pair donor. The Lewis acid moieties of said Lewis pair side chain moieties are each electrically connected to the conductive backbone.

Claims (52)

Claims
1. A polymer comprising a conductive backbone having a plurality of Lewis pair side chain moieties thereon, said Lewis pair side chain moieties each comprising: a Lewis acid moiety (LA) comprising an electron pair acceptor, and a Lewis base moiety (LB) comprising an electron pair donor, wherein the Lewis acid moieties of said Lewis pair side chain moieties are each electrically connected to the conductive backbone.
2. The polymer according to claim 1 , wherein said electron pair acceptor comprises a Group 13 element, such as boron or aluminium.
3. The polymer according to any claim 2, wherein said Group 13 element is boron.
4. The polymer according to any preceding claim, wherein the electron pair acceptor is bonded to one or more (e.g. two) RA moieties, the or each RA being independently selected from optionally substituted alkyl, alkenyl, alkynyl, aryl, heteroaryl, carbocyclic and heterocyclic; and/or wherein the electron pair acceptor is bonded to two or more moieties which, taken together with the electron pair acceptor to which they are bonded, form an optionally substituted 5- to 6-membered aromatic or 4- to 8-membered non-aromatic ring; and/or wherein the electron pair acceptor is bonded to two or more moieties which, taken together with the electron pair acceptor to which they are bonded, form an optionally substituted bicyclic ring moiety, each ring in the bicyclic ring independently being a 5- to 6- membered aromatic or 4- to 8-membered non-aromatic ring.
5. The polymer according to any preceding claim, wherein the electron pair acceptor is bonded to two RA moieties, optionally wherein said RA moieties are the same.
6. The polymer according to claim 4 or 5, wherein the one or more RA moieties are substituted by one or more of moieties independently selected from an optionally substituted aliphatic, heteroaliphatic, aromatic or heteroaromatic moiety, halogen, -NO2, -CN, -C(R)=C(R)2, -Câ ¡C-R , -OR , -SR', -S(0)R", -S02R', -SO3R , -S02N(R )2, -N(R)2, -[N(R)3]+, -NRC(0)R , -NRC(0)N(R)2, -NR CO2R, -NRSO2R', -NRS02N(R)2, -0-C(0)R , -0-C02R, -OC(0)N(R), -C(0)R, -CO2R, -C(0)N(R)2, -Si(R)3, -P(R)2, -[P(R')3]+, -P(0)(R)2, -P(0)(OR)2, -0-P(0)-OR, wherein R, independently, is hydrogen, halogen or aliphatic, heteroaliphatic, aromatic or heteroaromatic moiety, or two occurrences of R are taken together with their intervening atom(s) to form a 5-7-membered aromatic, heteroaromatic, cycloaliphatic, or heterocyclic ring, optionally wherein each R is, independently, substituted.
7. The polymer according to any one of claims 4 to 6, wherein the or each RA is independently selected from: wherein each R1 a is independently selected from an optionally substituted aliphatic, heteroaliphatic, aromatic or heteroaromatic moiety, halogen, -NO2, -CN, -C(R )=C(R )2, -OC-R , -OR , -SR', -S(0)R', -SO2R', -SO3R', -S02N(R)2, -N(R)2, -[N(R)3]+, -NRC(0)R , -NR C(0)N(R)2, -NRCO2R , -NR'S02R\ -NRS02N(R )2, -0-C(0)R , -O-CO2R , -OC(0)N(R ), -C(0)R', -CO2R', -C(0)N(R')2, -Si(R )3, -P(R)2, -[P(R')3]+, -P(0)(R")2, -P(0)(OR')2, -0-P(0)-OR, wherein R , independently, is hydrogen, halogen or aliphatic, heteroaliphatic, aromatic or heteroaromatic moiety, or two occurrences of R' are taken together with their intervening atom(s) to form a 5-7-membered aromatic, heteroaromatic, cycloaliphatic, or heterocyclic ring, optionally wherein each R is, independently, substituted; wherein n is selected from 0, 1 , 2, 3, 4 or 5; and optionally wherein each R' is, independently, substituted.
8. The polymer according to claim 7, wherein n is 1 , 2, 3 or 5, optionally wherein n is 5.
9. The polymer according to any one of claims 4 to 8, wherein the or each RA is independently selected from: wherein the or each R , independently, is as defined in claim 7.
10. The polymer according to any one of claims 7 to 9, wherein the or each R a is an electron withdrawing group.
1 1 . The polymer according to any one of claims 7 to 10, wherein the or each R1 a is independently selected from halogen, -C(0)R', -C02R , -C(0)N(R')2, halogen substituted aliphatic, -CN, -SO3R', -[N(R')3]+, or -N02.
12. The polymer according to any one of claims 7 to 1 1 , wherein the or each R a is a halogen, such as F, CI, Br; optionally wherein the or each R1a is F or CI, optionally wherein the or each R1a is F.
13. The polymer according to any one of claims 7 to 12, wherein the or each RA is independently selected from halophenyl, such as pentahalophenyl (e.g. pentafluorophenyl or pentachlorophenyl); 3,5 bis(trifluoromethyl)phenyl; 1 ,3,5 trimethyl phenyl; or wherein two said RA moieties form a bridged carbocycle bridged by the electron pair acceptor to which they are attached, optionally wherein the bridged carbocycle is a bridged cyclooctane.
14. The polymer according to claim 13, wherein the or each RA is pentafluorophenyl.
15. The polymer according to any one of claims 7 to 1 1 , wherein the or each R1a is halogen substituted aliphatic; optionally wherein the or each R a is trihalomethyl; optionally wherein the or each R1a is trifluoromethyl or trichloromethyl; optionally wherein the or each R1a is trifluoromethyl.
16. The polymer according to any preceding claim, wherein the electron pair donor is a Group 15 element, such as nitrogen or phosphorus.
17. The polymer according to claim 16, wherein the Group 15 element is nitrogen.
18. The polymer according to any preceding claim, wherein said backbone comprises a conjugated system.
19. The polymer according to any preceding claim, having the formula (I): wherein each RB is independently selected from hydrogen, optionally substituted alkyl, alkenyl, aryl, heteroaryl, carbocyclic and heterocyclic, and/or wherein two RB moieties, taken together with the intervening atoms to which they are bonded, form an optionally substituted fused 4- to 8-membered non-aromatic ring having 0-3 ring heteroatoms selected from the group consisting of N, O and S; and/or wherein two RB moieties, taken together with the intervening atoms to which they are bonded, form an optionally substituted bicyclic ring moiety, each ring in the bicyclic ring independently being a 5- to 6-membered aromatic or 4- to 8-membered non-aromatic ring; wherein XLB is the electron pair donor as defined in any preceding claim; wherein LA is the Lewis acid moiety as defined in any preceding claim; and wherein m is an integer of at least about 3; optionally greater than about 10.
20. The polymer according to claim 19, wherein the one or more RB moieties are substituted by one or more of moieties independently selected from an optionally substituted aliphatic, heteroaliphatic, aromatic or heteroaromatic moiety, halogen, -NO2, -CN, -C(R")=C(R")2, -Câ ¡C-R", -OR", -SR", -S(0)R'\ -SO2R", -S03R", -S02N(R")2, -N(R")2, -[N(R")3]+, -NR"C(0)R", -NR"C(0)N(R")2, -NR"C02R", -NR"S02R", -NR"S02N(R")2, -0-C(0)R", -0-C02R", -OC(0)N(R"), -C(0)R", -C02R", -C(0)N(R")2, -Si(R")3, -P(R")2, -[P(R")3]+, -P(0)(R")2, -P(0)(OR")2, -0-P(0)-OR", wherein R", independently, is hydrogen, halogen or aliphatic, heteroaliphatic, aromatic or heteroaromatic moiety, or two occurrences of R" are taken together with their intervening atom(s) to form a 5-7-membered aromatic, heteroaromatic, cycloaliphatic, or heterocyclic ring, optionally wherein each R" is, independently, substituted.
21. The polymer according to claim 19, wherein the one or more RB moieties are hydrogen, optionally wherein both RB moieties are hydrogen.
22. The polymer according to any preceding claim, wherein said backbone comprises pyrrole and/or thiophene moieties.
23. The polymer according to any preceding claim, wherein said backbone comprises pyrrole moieties.
24. A compound having the formula (II): wherein XLA is the electron pair acceptor according to any preceding claim; wherein XLB is the electron pair donor according to any preceding claim; wherein each RA is, independently, as defined in any one of claims 4 to 15; wherein each RB is, independently, as defined in any one of claims 19 to 21 ; and with the proviso that the compound is not:
25. The compound according to claim 24, with the proviso that the compound is not:
26. The compound according to claim 24 or 25, selected from:
27. The compound according to claim 24 or 25, wherein the compound is:
28. The compound according to claim 24 or 25, wherein the compound is:
29. Use of a compound having the formula (II): wherein XLA is the electron pair acceptor according to any one of claims 1 to 23; wherein XLB is the electron pair donor according to any one of claims 1 to 23; wherein each RA is, independently, as defined in any one of claims 4 to 15; wherein each RB is, independently, as defined in any one of claims 19 to 21 ; in the formation of a conductive polymer.
30. Use of a compound according to claim 29, wherein the compound is as defined in any one of claims 24 to 28.
31. A polymer comprising a conductive backbone having a plurality of Lewis pair side chain moieties thereon, said polymer being formed from polymerisation of one or more monomers, the one or more monomers comprising one or more compounds having the formula (III): wherein XLA is the electron pair acceptor according to any preceding claim; wherein XLB is the electron pair donor according to any preceding claim; wherein each RA is, independently, as defined in any one of claims 4 to 15; and wherein each RB is, independently, as defined in any one of claims 19 to 21.
32. The polymer according to claim 31 , wherein the one or more compounds are selected from:
33. The polymer according to claim 31 or 32, wherein the one or more compounds are selected from:
34. The polymer according to claim 31 or 32, wherein the one or more compounds are selected from:
35. The polymer according to claim 31 or 32, wherein the one or more compounds are selected from:
36. The polymer according to claim 31 or 32, wherein the one or more compounds are selected from:
37. The polymer according to claim 31 or 32, wherein the one or more compounds are selected from:
38. The polymer according to claim 31 or 32, wherein the one or more compounds are selected from:
39. The polymer according to any one of claims 31 to 38, wherein the one or more monomers further comprise pyrrole and/or thiophene, optionally pyrrole.
40. The polymer according to any one of claims 31 to 38, wherein the one or more monomers consist essentially of the compound(s).
41. The polymer according to any one of claims 31 to 40, wherein the polymer is a homopolymer or a co-polymer; optionally wherein the polymer is a homopolymer.
42. A polymer substantially as hereinbefore described with reference to the accompanying description and/or figures.
43. An electrode comprising a polymer according to any one of claims 1 to 23 or 31 to 42 present as one or more layers on the surface of said electrode.
44. The electrode according to claim 43, wherein said electrode comprises a carbon electrode, such as glassy carbon, graphite plate, or carbon fibre cloth.
45. An electrode substantially as hereinbefore described with reference to the accompanying description and/or figures.
46. A battery or capacitor comprising one or more polymers according any one of claims 1 to 23 or 31 to 42.
47. A battery or capacitor comprising one or more electrodes according to any one of claims 43 to 45.
48. A battery or capacitor substantially as hereinbefore described with reference to the accompanying description and/or figures.
49. A method of producing a polymer, comprising: polymerising one or more compounds as defined in claim 24 to 31 , optionally further comprising pyrrole and/or thiophene moieties, optionally pyrrole moieties.
50. The method of producing a polymer according to claim 49, wherein said polymerising is conducted by electropolymerisation.
51. The method of producing a polymer according to claim 49 or 50, wherein said polymerising is conducted under non-aqueous conditions (e.g. an organic, optionally halogenated solvent, such as dichloromethane).
52. A method of producing a polymer substantially as hereinbefore described with reference to the accompanying description and/or figures.
GB2001560.8A 2017-07-10 2018-07-10 Conductive polymers Withdrawn GB2579298A (en)

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WO2010075514A1 (en) * 2008-12-23 2010-07-01 Michigan Technological University Fluorescent conjugated polymers with a bodipy-based backbone and uses thereof
WO2010075512A1 (en) * 2008-12-23 2010-07-01 Michigan Technological University Polymers with bodipy-based backbone for solar cells
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WO2010075514A1 (en) * 2008-12-23 2010-07-01 Michigan Technological University Fluorescent conjugated polymers with a bodipy-based backbone and uses thereof
WO2010075512A1 (en) * 2008-12-23 2010-07-01 Michigan Technological University Polymers with bodipy-based backbone for solar cells
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