The electronic and electrochemical properties of poly(isothianaphthene)

Kobayashi, Masao; Colaneri, N.; Boysel, M.; Wudl, Fred; Heeger, Alan J.

doi:10.1063/1.448559

Cited by 384 publications

(154 citation statements)

References 20 publications

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“…This approach was first demonstrated by Wudl and coworkers in 1984 [5,6] with the polymerization of benzo[c]thiophene (1, R = H, Fig. 1).…”

Section: Introductionmentioning

confidence: 92%

“…1). The motivation behind this approach was the idea that the fusion of a second aromatic ring to the c-face of the thiophene would enhance the quinoidal nature of the polymer backbone, thus resulting in significant reductions of the band gap [1][2][3][4][5][6]. Following the initial success of benzo[c]thiophenes, other fused-ring variants soon followed including thieno [3,4-b]pyrazines (TPs, 2), and thieno [3,4-b]thiophenes (3) [1][2][3][4].…”

Section: Introductionmentioning

confidence: 99%

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Structure–function relationships in conjugated materials containing tunable thieno[3,4-b]pyrazine units

2012

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A series of 2,3-difunctionalized 5,7-bis(2-thienyl)thieno[3,4-b]pyrazines containing electron-donating and electron-withdrawing side chains are reported to evaluate the potential tuning effect of the side chains on the electronic properties of these common terthienyl building blocks. In order to further study the resulting effects of such side chains in polymeric materials, the dihexyloxy-functionalized terthienyl was copolymerized with fluorene and its electronic properties compared with a number of analogous materials.

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“…This approach was first demonstrated by Wudl and coworkers in 1984 [5,6] with the polymerization of benzo[c]thiophene (1, R = H, Fig. 1).…”

Section: Introductionmentioning

confidence: 92%

Section: Introductionmentioning

confidence: 99%

Structure–function relationships in conjugated materials containing tunable thieno[3,4-b]pyrazine units

2012

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“…PITN, due to its low band gap arising from the ringfusing effect of benzene on the polythiophene backbone, shows high intrinsic conductivity without the doping process, thus leading to good environmental stability. 11 High conductivity and thermal stability are, no doubt, essential if one considers using PITN as a filling component.…”

Section: Introductionmentioning

confidence: 99%

All polymer PTC devices: Temperature‐conductivity characteristics of polyisothianaphthene and poly(3‐hexylthiophene) blends

Liu

Oshima

Shimomura

et al. 2005

J of Applied Polymer Sci

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ABSTRACT:The present article is concerned with the temperature-conductivity characteristics of blends consisting of polyisothianaphthene (PITN) particles and a soluble poly(3-hexylthiophene) (P3HT). PITN was synthesized by direct conversion of 1,3-dihydroisothianaphthene (DHITN) monomer using N-chlorosuccinimide (NCS) as an oxidation/dehydrogenation reagent. The high conductivity and thermal stability of the doped and dedoped PITN were confirmed. Microscopic investigation by scanning electron microscopy (SEM) showed that the as-prepared PITN exhibited diversified shapes and sizes, with large rectangular particles having an average size of 2 ϳ 5m and fine round particles ranging from 0.1 to 0.3 m. The PITN particles were blended with the chemically synthesized P3HT as a high conductivity component to improve the conductivity and simultaneously maintain the positive temperature coefficient (PTC) effect of the original P3HT near its melting point. The temperature-conductivity characteristics for PITN-P3HT blends with various PITN contents showed that a blend having both a high conductivity (nearly 3 ϳ 4 orders higher than that of the original P3HT) and a good PTC intensity could be obtained with a PITN content of 20 ϳ 25%. The different temperature-conductivity behavior of P3HT blends filled with PITN as compared to other conducting particles, for example, carbon black, was explained by its unique dispersion structure due to a relatively higher adhesive interaction of PITN particles with the P3HT matrix during the precipitation process. The results from heating recycles revealed that the PTC effect of PITN-P3HT blends was not just related to the conductivity decrease of the P3HT matrix, arising from the conformational change of the conjugated backbone during the melting, but also to the dilution effect of the conducting percolation network due to the mobility of PITN particles induced by the viscosity decrease of the P3HT matrix.

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“…DHITN was synthesized according to Cava's method 23 and purification was confirmed by 1 H NMR, 13 C NMR, and UV-VIS absorption spectra.…”

Section: Synthesesmentioning

confidence: 99%

Synthesis of Poly(isothianaphthene) by Photopolymerization of 1,3-Dihydroisothianaphthene

Kitano

Iyoda

Shimidzu

1995

Polym J

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ABSTRACT:A conducting polymer, poly(isothianaphthene) (PITN) was prepared by direct photopolymerization in solution of 1,3-dihydroisothianaphthene (DHITN) which was more stable in air than isothianaphthene (ITN). This photopolymerization was initiated with electron transfer from DHITN to an acceptor such as carbon tetrachloride or oxygen. It proceeded by both UV irradiation and cationic polymerization under light exclusion. The polymerization rate was accelerated by the addition of salts. The rate of the PITN fraction of the product composition was governed by the nucleophilicity of the anion species of added salts. The features of this polymerization were seen in electrochemical polymerization and photopolymerization of ITN.KEY WORDS Poly(isothianaphthene) / Photopolymerization / Dihydroisothianaphthene / Recently, special interest has been drawn to a small band-gap polymer in experiential and theoretical approaches. Poly(naphthothiophene), 1 poly(dithieno-thiophene), 2 -4 poly-(thienobenzene), 5 and poly(dioxymethyleneisothianaphthene)6 were recently synthesized. The band gaps of some polymers were calculated. 7 -12 In the conducting polymers, poly-(isothianaphthene) (PITN) has a smallest band gap (1.1 eV) and the conducting doped state gives transparency in visible region. 13 -14 Both conspicuous properties are explained by the large quinoidic character of the polymer backbone geometry or electronic structure. 15 -1 7 PITN has so far been prepared by electrochemical or chemical polymerization 18 of its monomer, isothianaphthene (ITN).Recently, we reported a new preparative method of PITN by the direct photopolymerization of ITN to provide photochemical micro-fabrication of PITN-based electrically conducting polymer thin film. 19 Here, we report the details of this oxygeninduced polymerization ofDHITN, that is, the photopolymerization of DHITN. EXPERIMENT AL AnalysisThe UV-VIS absorption spectra were recorded on a Shimadzu MPS-2000 or Shimadzu UV-2200 spectrophotometer and fluorescence spectra were recorded on a Shimadzu RF-503A spectrofluorometer. 1 H NMR and 13 C NMR spectra were recorded on a JEOL EX-90 spectrometer. Infrared absorption spectra were recorded on a Nicolet 20 DXB spectro-875

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The electronic and electrochemical properties of poly(isothianaphthene)

Cited by 384 publications

References 20 publications

Structure–function relationships in conjugated materials containing tunable thieno[3,4-b]pyrazine units

Structure–function relationships in conjugated materials containing tunable thieno[3,4-b]pyrazine units

All polymer PTC devices: Temperature‐conductivity characteristics of polyisothianaphthene and poly(3‐hexylthiophene) blends

Synthesis of Poly(isothianaphthene) by Photopolymerization of 1,3-Dihydroisothianaphthene

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