TY - JOUR
T1 - Synthesis of self-threading bithiophenes and their structure-property relationships regarding cyclic side-chains with atomic precision
AU - Ouchi, Yuki
AU - Sugiyasu, Kazunori
AU - Ogi, Soichiro
AU - Sato, Akira
AU - Takeuchi, Masayuki
PY - 2012/1/2
Y1 - 2012/1/2
N2 - 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, 1H 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.
AB - 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, 1H 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.
KW - molecular wires
KW - oligomers
KW - side-chains
KW - structure-property relationships
KW - thiophenes
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U2 - 10.1002/asia.201100524
DO - 10.1002/asia.201100524
M3 - Article
C2 - 22095959
AN - SCOPUS:84255169500
VL - 7
SP - 75
EP - 84
JO - Chemistry - An Asian Journal
JF - Chemistry - An Asian Journal
SN - 1861-4728
IS - 1
ER -