NDLI: Synthesis, Properties, and π-Dimer Formation of Oligothiophenes Partially Bearing Orthogonally Fused Fluorene Units

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Synthesis, Properties, and π-Dimer Formation of Oligothiophenes Partially Bearing Orthogonally Fused Fluorene Units

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Ie, Yutaka Aso, Yoshio Okamoto, Yuji Tone, Saori
Description	Author Affiliation: Ie Y ( The Institute of Scientific and Industrial Research (ISIR), Osaka University, 8-1 Mihogaoka, Ibaraki, Osaka 567-0047 (Japan). yutakaie@sanken.osaka-u.ac.jp.); Okamoto Y ( The Institute of Scientific and Industrial Research (ISIR), Osaka University, 8-1 Mihogaoka, Ibaraki, Osaka 567-0047 (Japan).); Tone S ( The Institute of Scientific and Industrial Research (ISIR), Osaka University, 8-1 Mihogaoka, Ibaraki, Osaka 567-0047 (Japan).); Aso Y ( The Institute of Scientific and Industrial Research (ISIR), Osaka University, 8-1 Mihogaoka, Ibaraki, Osaka 567-0047 (Japan). aso@sanken.osaka-u.ac.jp.)
Abstract	A series of oligothiophenes that incorporate cyclopenta[c]thiophene-based units bearing spiro-substituted dialkylfluorene was synthesized. Photophysical measurements indicated that there was no interruption in the conjugation along the oligothiophene backbones, irrespective of the number or position of this unit. Electrochemical measurements showed that the thiophene 7-mers and 11-mer exhibit reversible multi-oxidation waves. The formation of cationic species was clearly observed from UV/Vis/NIR measurements. Furthermore, the UV/Vis/NIR spectra at 223 K under one-electron oxidation conditions revealed that the unsubstituted thiophene or bithiophene units remained in the absence of intermolecular π–π interactions, whereas the formation of π-dimeric species was observed for the thiophene 7-mer containing an unsubstituted terthiophene $(U_{3})$ unit. Theoretical calculations indicated that the combination of the $U_{3}$ unit and the all-trans conformation decreased the intermolecular steric repulsion between the fused cyclopentene ring and its facing thiophene, which may contribute to the formation of the dimeric structure.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	46
Volume Number	21
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2015-11-09
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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