Carbon-Bridged Oligo(phenylene vinylene)s: A de Novo Designed, Flat, Rigid, and Stable π-Conjugated System
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- Hayato Tsuji
- Department of Chemistry, Faculty of Science, Kanagawa University, 2946 Tsuchiya, Hiratsuka 259-1293, Japan
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- Eiichi Nakamura
- Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
書誌事項
- 公開日
- 2019-09-16
- 資源種別
- journal article
- 権利情報
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- https://doi.org/10.15223/policy-029
- https://doi.org/10.15223/policy-037
- https://doi.org/10.15223/policy-045
- DOI
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- 10.1021/acs.accounts.9b00369
- 公開者
- American Chemical Society (ACS)
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説明
The modern history of conducting organic systems started with a fortuitous error in 1967 on acetylene polymerization, followed by a rational discovery in 1976 on the effects of doping that generates a polaron and, hence, dramatically increases conductivity. Not unexpectedly, however, the prototypical polyacetylene suffers many problems, including C-C single bond rotation, short effective conjugation length, radiationless deactivation, and instability of the polarons. Several strategies have been put in place to solve these problems. An early approach relied on partial rigidification of the polyene structure by conversion into polymers with thiophene, pyrrole, and benzene linkages. An oligo(phenylene vinylene) (OPV) is an all-carbon analogue of polyacetylene, where every other diene unit in the polyene chain is converted to a benzene unit, still leaving many C-C single bonds freely rotating in the molecule. We considered adding additional carbon bridges to rigidify the OPV skeleton entirely to create a carbon-bridged OPV (COPV). Making such a compound was an obvious challenge. This Account describes the authors' efforts to design and synthesize a series of COPV molecules, where the benzene rings in OPV are bridged by sp
収録刊行物
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- Accounts of Chemical Research
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Accounts of Chemical Research 52 (10), 2939-2949, 2019-09-16
American Chemical Society (ACS)