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A concise synthesis and electrochemical behavior of functionalized poly(thieno[3,4-b]thiophenes): New conjugated polymers with low bandgap
Authors:Jin Hong Park  Dae Hyun Yoon  Soo-Hyoung Lee  Kyukwan Zong
Institution:a Institute of Fusion Science, Division of Science Education, Chonbuk National University, Jeonju 561-756, South Korea
b Department of Chemical Engineering, Nanomaterials Processing Research Center, Chonbuk National University, Jeonju 561-756, South Korea
c Department of Printed Electronics Engineering, Sunchon National University, Sunchon 540-742, South Korea
Abstract:New thieno3,4-b]thiophene derivatives were prepared via a short and versatile synthetic route. Electrochemical studies of 2-heptenylthieno3,4-b]thiophene, 2-styrylthieno3,4-b]thiophene, and 2-phenyl-3-(thieno3,4-b]thiophene-2-yl)acrylonitrile and the corresponding polymers revealed that raising the HOMO and lowering the LUMO can be attained by functionalizing thieno3,4-b]thiophene with aromatic resonance-enhancing and electron-withdrawing groups. The bandgap of resulting polymers varied from 0.78 to 1.0 eV, indicating that poly(2-phenyl-3-(thieno3,4-b]thiophene-2-yl)acrylonitrile) is one of the lowest bandgap polymers ever reported.
Keywords:Conjugated polymer  Low-bandgap polymer  Thienothiophene  n-Doping
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