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Materials 2010, 3(10), 4773-4783; doi:10.3390/ma3104773

Postfunctionalization of Alkyne-Linked Conjugated Carbazole Polymer by Thermal Addition Reaction of Tetracyanoethylene

1
Global Edge Institute, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8550, Japan
2
PRESTO, Japan Science and Technology Agency (JST), 4-1-8 Honcho, Kawaguchi, Saitama, Japan
3
Department of Organic and Polymeric Materials, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8552, Japan
*
Author to whom correspondence should be addressed.
Received: 23 August 2010 / Revised: 26 September 2010 / Accepted: 14 October 2010 / Published: 15 October 2010
(This article belongs to the Special Issue Solar Energy Materials)
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Abstract

The postfunctionalization of the main chain alkyne moieties of carbazole containing poly(arylenebutadiynylene)s was attempted by using a high yielding addition reaction between electron rich alkynes and a strong acceptor molecule, tetracyanoethylene (TCNE). After successful postfunctionalization, the polymer band gap decreased due to the intramolecular donor-acceptor interactions. The resulting donor-acceptor alternating polymer showed a very broad charge-transfer band in the visible region as well as redox activities in both anodic and cathodic directions. The optical band gap showed good agreement with the electrochemical band gap. Furthermore, the thermal stability was enhanced after postfunctionalization. These features of the donor-acceptor alternating polymer are expected to be useful for high performance activities in organic solar cell applications.
Keywords: addition reaction; charge-transfer band; conjugated polymer; electrochemistry; postfunctionalization addition reaction; charge-transfer band; conjugated polymer; electrochemistry; postfunctionalization
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MDPI and ACS Style

Michinobu, T.; Fujita, H. Postfunctionalization of Alkyne-Linked Conjugated Carbazole Polymer by Thermal Addition Reaction of Tetracyanoethylene. Materials 2010, 3, 4773-4783.

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