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Design of Narrow-Bandgap Polymers. Syntheses and Properties of Monomers and Polymers Containing Aromatic-Donor and o-Quinoid-Acceptor Units
Abstract
A series of novel monomers and polymers containing aromatic-donor and o -quinoid-acceptor units was prepared, and the relationship between their spectral and electrochemical properties and their structures was investigated. X-ray structure analyses of the monomers possessing thiophene units revealed coplanar conformations, whereas calculations of the monomers containing N -methylpyrrole showed torsional conformations. Cyclic voltammetry showed amphoteric properties for all the monomers and p- and n-doping processes for most of the polymers. The reduction potentials were primarily dependent on the electron-accepting character of the o -quinoid-acceptor units. The electrochemical behavior of the polymers was characterized by cyclic voltammetry and suggested narrow-bandgap systems. The bandgaps determined from optical absorption spectra range from 0.5 to 1.4 eV. The polymer composed of thiophenes and benzo[1,2- c;3,4- c ‘]bis[1,2,5]thiadiazole exhibited the narrowest bandgap.
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Cited by
Electrochemistry of Conducting Polymers—Persistent Models and New Concepts
Heinze, J., Frontana-Uribe, B. A., & Ludwigs, S. (2010) · Chemical Reviews · doi:10.1021/cr900226k · Cited by 1,258
Organic and Polymeric Semiconductors Enhanced by Noncovalent Conformational Locks
Huang, H., Yang, L., Facchetti, A., & Marks, T. J. (2017) · Chemical Reviews · doi:10.1021/acs.chemrev.7b00084 · Cited by 804
Low bandgap semiconducting polymers for polymeric photovoltaics
Liu, C., Wang, K., Gong, X., & Heeger, A. J. (2016) · Chemical Society Reviews · doi:10.1039/c5cs00650c · Cited by 555
Neto, B. A. D., Lapis, A. A. M., da Silva Júnior, E. N., & Dupont, J. (2013) · European Journal of Organic Chemistry · doi:10.1002/ejoc.201201161 · Cited by 328
Chen, C.-H., Hsieh, C.-H., Dubosc, M., Cheng, Y.-J., & Hsu, C.-S. (2010) · Macromolecules · doi:10.1021/ma902206u · Cited by 195
Metadata
- Authors
- Kitamura, C., Tanaka, S., & Yamashita, Y.
- Venue
- Chemistry of Materials
- Publisher
- American Chemical Society (ACS)
- Published
- 1996-01-01
- Volume
- 8
- Issue
- 2
- Pages
- 570-578
- ISSN
- 0897-4756 (ISSN-L)
- 1520-5002
- OpenAlex
- W2005753285
- Cited by
- 509
- References
- 0
- FWCI
- 9.22
- Type
- journal article
- Language
- en
- Open access
- closed
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- Kitamura, C., Tanaka, S., & Yamashita, Y. (1996). Design of Narrow-Bandgap Polymers. Syntheses and Properties of Monomers and Polymers Containing Aromatic-Donor and o-Quinoid-Acceptor Units. Chemistry of Materials. https://doi.org/10.1021/cm950467m
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