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Synthesis of Self‐Threading Bithiophenes and their Structure–Property Relationships Regarding Cyclic Side‐Chains with Atomic Precision
Author(s) -
Ouchi Yuki,
Sugiyasu Kazunori,
Ogi Soichiro,
Sato Akira,
Takeuchi Masayuki
Publication year - 2012
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201100524
Subject(s) - dihedral angle , side chain , monomer , polythiophene , materials science , threading (protein sequence) , spectroscopy , molecular wire , crystallography , chemistry , polymer , molecule , organic chemistry , conductive polymer , hydrogen bond , composite material , biochemistry , physics , quantum mechanics , protein structure
We have recently reported a self‐threading polythiophene as a new family of insulated molecular wires. Herein, we focused on the structure–property relationships of the unique three‐dimensional architecture of the monomer. We have synthesized nine self‐threading bithiophene monomers that have cyclic side‐chains of different size and flexibility: i.e., 21‐, 22‐, 23‐, 24‐, 26‐, and 30‐membered rings composed of paraffinic, olefinic, or alkynic chains. To investigate their structure–property relationships, 1 H NMR spectroscopy, UV absorption, and fluorescence spectroscopy measurements were conducted. We found that cyclic side‐chains define the movable range of the dihedral angle of the bithiophene backbone, thereby affecting its photophysical properties. Therefore, the ability to design a structure with atomic precision as described herein would lead to the fine‐tuning of the electronic properties of insulated molecular wires.