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End‐Capping π‐Conjugated Systems with Medium‐Sized Sulfur‐Containing Rings: A Route Towards Solution‐Processable Air‐Stable Semiconductors
Author(s) -
Fukazawa Aiko,
Toda Yusuke,
Hayakawa Masahiro,
Sekioka Anna,
Ishii Hiroyuki,
Okamoto Toshihiro,
Takeya Jun,
Hijikata Yuh,
Yamaguchi Shigehiro
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201802656
Subject(s) - steric effects , conjugated system , intermolecular force , solubility , materials science , sulfur , crystallography , semiconductor , electrochemistry , chemistry , polymer , stereochemistry , polymer chemistry , nanotechnology , organic chemistry , molecule , optoelectronics , electrode
The sulfur‐containing nine‐membered heterocycle thiacyclononene (TN) was evaluated as a new type of end‐capping group for π‐conjugated systems. A systematic study on TN‐capped α‐oligothiophenes ( TNnTs ; n=4–7) revealed that the capping with TN, which adopts a bent conformation, imparts the resulting oligothiophenes with drastically increased solubility at approximately 140 °C and high electrochemical stability, whereas the electronic structure remains virtually unperturbed. The even‐numbered oligothiophenes TN4T and TN6T form characteristic offset herringbone‐type packing structures on account of the steric repulsion between the TN rings and the presence of intermolecular nonbonding S⋅⋅⋅S interactions. This packing mode in combination with the high solubility enabled the solution‐process fabrication of field‐effect transistors based on TN6T , which exhibited a high performance without degradation even upon exposure to air.