GB2304722A - Intrinsically conductive organic polymers - Google Patents
Intrinsically conductive organic polymers Download PDFInfo
- Publication number
- GB2304722A GB2304722A GB9517413A GB9517413A GB2304722A GB 2304722 A GB2304722 A GB 2304722A GB 9517413 A GB9517413 A GB 9517413A GB 9517413 A GB9517413 A GB 9517413A GB 2304722 A GB2304722 A GB 2304722A
- Authority
- GB
- United Kingdom
- Prior art keywords
- poly
- electron
- functionalities
- component
- backbone
- 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.)
- Granted
Links
- 229920000620 organic polymer Polymers 0.000 title description 6
- 229920001940 conductive polymer Polymers 0.000 claims abstract description 8
- 229920000547 conjugated polymer Polymers 0.000 claims abstract description 4
- 230000000295 complement effect Effects 0.000 claims abstract description 3
- 230000007704 transition Effects 0.000 claims abstract 2
- -1 poly(2,5 thiophenediyl) Polymers 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229920003026 Acene Polymers 0.000 claims description 2
- 239000002019 doping agent Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- XWUCFAJNVTZRLE-UHFFFAOYSA-N 7-thiabicyclo[2.2.1]hepta-1,3,5-triene Chemical compound C1=C(S2)C=CC2=C1 XWUCFAJNVTZRLE-UHFFFAOYSA-N 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000002861 polymer material Substances 0.000 claims 1
- 239000002322 conducting polymer Substances 0.000 abstract description 5
- 229920000642 polymer Polymers 0.000 description 25
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000000370 acceptor Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920001197 polyacetylene Polymers 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000037230 mobility Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- H01B1/124—Intrinsically conductive polymers
- H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
-
- 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
- H01B1/124—Intrinsically conductive polymers
- H01B1/128—Intrinsically conductive polymers comprising six-membered aromatic rings in the main chain, e.g. polyanilines, polyphenylenes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10N—ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10N60/00—Superconducting devices
- H10N60/80—Constructional details
- H10N60/85—Superconducting active materials
- H10N60/851—Organic superconductors
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Organic conducting polymers with high conductivity, which (in some cases) show a transition to a superconducting state at low temperatures consist of complementary pairs of conjugated polymers, functionalised with donor and acceptor substituents respectively.
Description
- INTRINSICALLY CONDUCTIVE ORGANIC POLYMERS
DESCRIPTION
BRIEF BACKGROUND DETAILS
Conventional conducting polymers such as polyacetylene possess conjugated carbon, carbocyclic or heterocyclic backbones. When pure, they are in general weakly semiconducting, and are rendered conductive via charge-transfer or by the induction of mobile charges on the polymer chains, balanced by suitable counter-ions.
The counter-ions can impose severe limitations on the attainment of high conductivity or superconductivity for a variety of reasons. At low concentration, small ions located between the chains tend to immobilise the charge carriers in the polymer by virtue of their strong mutual Coulombic attraction; this effect is less important (but still significant) at higher concentrations, when the charges are more effectively screened from each other. On the other hand, bulky counter-ions have a weaker Coulombic effect but a greater tendency to disrupt the structural perfection of the polymer chains; this can greatly reduce the effective delocalisation of the electron states, and again immobilise the charge carriers.
PRINCIPLE OF mE INVENTION
It is reasonable to suggest that an 51 ideal " counter-ion would have a well-distributed compensating charge to minimise the
Coulomb effect on the charge in the polymer, while being highly compatible with the crystal structure of the polymer to avoid structural disorder or torsion of the polymer backbones. The present invention relies upon the use of two complementary conducting polymer backbones, chosen to be structurally compatible with each other, both being chemically substituted in order to favour charge-transfer doping between the two polymers.
This is clearly to be distinguished from simple organic chargetransfer salts, in which the conducting "pathway" comprises a Co- - INTRINSICALLY CONDUCTIVE ORGANIC POLYMERS facial assembly of planar or discotic molecules in segregated stacks [e.g. tetrafulvalenium tetracyanoquinodimethanide, TTF
TCNQ]. The salts are essentially brittle ionic solids, whereas the polymers are mechanically superior and [in certain cases] thermoplastic and processible.Another important distinction is that the nature of the long-range electron delocalisation is different in the two types of material: in the present invention it occurs primarily via covalent conjugative overlap of the orbitals [e.g. carbon(2p)l within each long polymer molecule, whereas in the salts it arises primarily through intermolecular orbital overlap between small conjugated units. Furthermore the molecular arrangement of the polymer chains for materials as described herein will generally have alternating electron-rich and electron-deficient chains packed together, whereas traditional charge-transfer salts are only highly conductive when they consist of segregated donor and acceptor stacks [as in TTF TCNQJ.
EMBODIHENTS OF THE INVENTION
In general, to put the invention into practice it is not desirable to use polymers based on the simplest conjugated polymer, polyacetylene. This is because an orderly crystalline packing of polyacetylene chains doped alternately with strong electron donors and acceptors will be prone to undergo Diels
Alder cyclisation reactions (leading to heavy cross-linking and loss of conjugation). Therefore the backbones will preferably be based on aromatic or hetero-aromatic units, as in the most stable conventional conducting polymers such as polythiophene [poly(2,5thiophenediyl]).
The invention requires the bringing together of equivalent numbers of conjugated polymer chains (respectively carrying donor and acceptor substituents), preferably to form an ordered crystalline arrangement. It is not essential, but will often be convenient, to use the following sequence of steps to achieve this:
- INTRINSICALLY CONDUCTIVE ORGANIC POLYMERS (i) syntheses of the donor- and acceptor-substituted
monomers; (ii) separate polymerisation of these by conventional
methods to form the component polymers; (iii) purification of the polymers (if soluble) via re
precipitation, using an alternating combination of
good and poor solvents: this is not an unconventional
process, but will usually be a very important step, in
order to remove harmful electrically-active impurities
such as inorganic anions; (iv) preparation of (normally dilute) solutions of the two
polymers in suitable miscible solvents; (v) mixing the polymer solutions in electrically
equivalent proportions and, after permitting the
charge-transfer to occur, isolation of the required
final product by filtration (if insoluble) or by
vacuum-evaporation of the solvent mixture; finally
washing, and drying under vacuum.
To enable workers competent in the relevant science to understand the preparation more fully, the following more specific information is provided:
The "electron-deficient" component in the final material may be derived from an aromatic or heteroaromatic polymer such as poly(l,4-phenylenediyl), poly(2,5-thiophenediyl), poly(2,5- pyrrolediyl), poly(1,4-phenylene vinylene), poly(3,6- pyridazinediyl), "polyaniline" [also known as poly(l,4phenyleneamineimine) or polybenzeneamine], poly(1,4-phenylene sulphide), polyphenothiazine or polyquinoxaline.The "electronrich' component can be derived from any of the above except polyaniline, poly(pyrrolediyl) or polyquinoxaline, which are not amphoteric and can only be doped p-type; additionally poly(2,5pyridinediyl) could be used as the basis of this component.
The requisite charge-transfer is provided by suitable substituents placed at regular intervals along each of the polymer backbones (but not necessarily on every monomer unit).
- INTRINSICALLY CONDUCTIVE ORGANIC POLYMERS
Thus for example either poly(3-cyano-2,5-thiophenediyl) or an alternating copolymer of this with poly(2,5-thiophenediyl) could act as an electron-accepting polymer. [Other well-known electronacceptor substituents could be used instead of cyanide (nitrile), notably nitro, halo (especially fluoro) or carboxyl moieties).]
More complex examples having this type of substituent include poly(3-picryl-2,5-thiophenediyl), poly[3-(4trifluoromethylphenyl)thiophene-2,5-diyl] and poly[3thiophene(2,5-diyl)malonic acid].
The electron-donating polymer is similarly substituted at regular intervals along its backbone (but not necessarily on every monomer unit) by donor moieties such as alkyl, alkyloxy or alkylthio groups). Examples of such polymers include poly(3,4dimethoxy-2,5-thiophenediyl) or poly(3,4-dimercapto-2,5- thiophenediyl), or regular copolymers of these with poly(2,5thiophenediyl). More complex examples which may be cited as having this type of substituent include poly[3-(4-methylthio)phenyl-2,5-thiophenediyl] and poly(3,4-ethanedioxa-2,5thiophenediyl).
An example based on another backbone is poly(2,5-dimethoxy-l,4phenylenevinylene).
Materials of the type defined in this Description are essentially polymer blends, of a distinctive and novel kind. It should be understood that not all possible combinations of donor and acceptor polymers within the scope of the invention are miscible; there are strict thermodynamic limitations on the miscibility of most polymers in solution, and especially in the solid state.
However, the presence of polar interactions between the polymer pairs in these systems confers the additional benefit of improved miscibility in general.
In a limited number of cases, the polymers are expected to show superconduction at low temperatures (especially for ladderstructured polymers based on polyquinoxaline or polyacenes), but
- INTRINSICALLY CONDUCTIVE ORGANIC POLYMERS the primary advantage of this class of material compared with conventional electronically conductive polymers is that of superior carrier mobilities and hence higher conductivities in the vicinity of ambient temperature. This is achieved without the need of foreign redox or protonating dopant additives, and consequently without the poor intrinsic or environmental stability that usually results from the necessity for such additives in conventional conducting polymers.
Claims (11)
1. A method of preparing an electrically conductive polymer material
by bringing together electrically equivalent quantities of two
complementary conjugated polymers, one being chosen to be
relatively electron-rich and the other electron-poor, such that
each component acts both as a polymeric dopant and a conductive
polymer.
2. A method according to claim 1, wherein the component which is
initially electron-rich is based on a backbone of poly(2,5
thiophenediyl), poly(2,5-pyrrolediyl), poly(1,4-phenylene vinylene), poly(1,4-phenylenediyl), poly(3,6-pyridazinediyl),
poly(l,4-phenylene sulphide), npolyaniline" [poly(l,4- phenyleneamineimine)], polyphenothiazine, polyquinoxaline or
polyacene.
3. A method according to claim 2, wherein the component which is
initially electron-rich is made so by substitution of the
repeating units in the backbone at regular intervals by electron
donating functionalities.
4. A method according to claim 3, wherein the electron-donating
functionalities are alkyl, alkyloxy, ethanedioxy or alkylthio
groups.
5. A method according to claim 3, wherein the electron-donating
functionalities are simple or condensed aryl ring systems
substituted by one or more alkyl, alkyloxy, ethanedioxy,
alkylthio or alkyldithio groups.
6. A method according to claim 1, wherein the component which is
initially electron-poor is based on a backbone of poly(2,5
thiophenediyl), poly(l,4-phenylene vinylene), poly(l , 4- phenylenediyl), poly( 1, 4-phenylene sulphide), polyphenothiazine
or poly(2,5-pyridinediyl).
7. A method according to claim 6, wherein the component which is
initially electron-poor is made so by substitution of the
repeating units in the backbone at regular intervals by electron
withdrawing functionalities.
8. A method according to claim 7, wherein the electron-withdrawing
functionalities are cyano, nitro, halogen, carboxyl or
trifluoromethyl groups.
9. A method according to claim 7, wherein the electron-withdrawing
functionalities are aryl ring systems substituted by one or more
cyano, nitro, halogen, carboxyl or trifluoromethyl groups.
10. A polymeric material, prepared substantially in accordance with
any previous claim, and characterised by electrically conductive
or semiconductive properties.
11. A polymeric material as in claim 10, which undergoes a transition
to a superconducting state on cooling.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9517413A GB2304722B (en) | 1995-08-25 | 1995-08-25 | Intrinsically conductive organic polymers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9517413A GB2304722B (en) | 1995-08-25 | 1995-08-25 | Intrinsically conductive organic polymers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB9517413D0 GB9517413D0 (en) | 1995-10-25 |
| GB2304722A true GB2304722A (en) | 1997-03-26 |
| GB2304722B GB2304722B (en) | 1999-12-01 |
Family
ID=10779739
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9517413A Expired - Fee Related GB2304722B (en) | 1995-08-25 | 1995-08-25 | Intrinsically conductive organic polymers |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2304722B (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2124635A (en) * | 1982-08-02 | 1984-02-22 | Raychem Ltd | Polymer composition |
| EP0160207A1 (en) * | 1984-04-02 | 1985-11-06 | Polaroid Corporation | Processable conductive polymers |
-
1995
- 1995-08-25 GB GB9517413A patent/GB2304722B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2124635A (en) * | 1982-08-02 | 1984-02-22 | Raychem Ltd | Polymer composition |
| EP0160207A1 (en) * | 1984-04-02 | 1985-11-06 | Polaroid Corporation | Processable conductive polymers |
Also Published As
| Publication number | Publication date |
|---|---|
| GB9517413D0 (en) | 1995-10-25 |
| GB2304722B (en) | 1999-12-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Blanchard et al. | Triphenylamine and some of its derivatives as versatile building blocks for organic electronic applications | |
| Baeuerle et al. | Electronic structure of mono-and dimeric cation radicals in end-capped oligothiophenes | |
| Shi et al. | Distannylated Bithiophene Imide: Enabling High‐Performance n‐Type Polymer Semiconductors with an Acceptor–Acceptor Backbone | |
| Hotta et al. | Conducting polymer composites of soluble polythiophenes in polystyrene | |
| Yue et al. | Effect of sulfonic acid group on polyaniline backbone | |
| Ding et al. | Influence of backbone curvature on the organic electrochemical transistor performance of glycolated donor–acceptor conjugated polymers | |
| Blouin et al. | Optical, electrochemical, magnetic, and conductive properties of new polyindolocarbazoles and polydiindolocarbazoles | |
| AU2010254138A1 (en) | Green soluble conjugated polymers with high charge carrier mobilities | |
| Dhawan et al. | Influence of polymerization conditions on the properties of poly (2-methylaniline) and its copolymer with aniline | |
| Durand et al. | Single Ether‐Based Side Chains in Conjugated Polymers: Toward Power Factors of 2.9 mW m− 1 K− 2 | |
| Tan et al. | Design and synthesis of ferrocene-terminated hyperbranched polyimide for memory devices | |
| Ertan et al. | A platform to synthesize a soluble poly (3, 4‐ethylenedioxythiophene) analogue | |
| Mueller et al. | EDOT‐diketopyrrolopyrrole copolymers for high bulk hole mobility and near infrared absorption | |
| Blouin et al. | Optical, electrochemical, magnetic, and conductive properties of new poly (indolocarbazole‐alt‐bithiophene) s | |
| Bouguerra et al. | Synthesis and Photophysical and Electroluminescent Properties of Poly (1, 4-phenylene–ethynylene)-alt-poly (1, 4-phenylene–vinylene) s with Various Dissymmetric Substitution of Alkoxy Side Chains | |
| Ranger et al. | Novel base-dopable poly (2, 7-fluorenylene) derivatives | |
| Sommer | Development of conjugated polymers for organic flexible electronics | |
| Zhang et al. | Rational design of diarylethylene‐based polymeric semiconductors for high‐performance organic field‐effect transistors | |
| Schmatz et al. | Multifunctional triphenylamine polymers synthesized via direct (hetero) arylation polymerization | |
| Song et al. | Synthesis and memory characteristics of highly organo‐soluble hyperbranched polyimides with various electron acceptors | |
| Ayuk Mbi Egbe et al. | Combined effects of conjugation pattern and alkoxy side chains on the photovoltaic properties of thiophene‐containing PPE‐PPVs | |
| Farcas et al. | Synthesis and electro‐optical properties of polyfluorene modified with randomly distributed electron‐donor and rotaxane electron‐acceptor structural units in the main chain | |
| Yasa et al. | Thieno [3, 4‐c] pyrrole‐4, 6‐dione‐Based Conjugated Polymers for Nonfullerene Organic Solar Cells | |
| Li et al. | Novel narrow‐band‐gap conjugated copolymers containing phenothiazine‐arylcyanovinyl units for organic photovoltaic cell applications | |
| Ye et al. | Polymer memory devices with widely tunable memory characteristics based on functional copolynaphthalimides bearing varied fluorene and triphenylamine moieties |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 20110825 |