Synthesis of penta- and hexa(3,4-thienylene): size-dependent structural properties of cyclic oligothiophenes

Mai Nagase; Sachiko Nakano; Yasutomo Segawa

doi:10.1039/d3cc03508e

Synthesis of penta- and hexa(3,4-thienylene): size-dependent structural properties of cyclic oligothiophenes

Chem Commun (Camb). 2023 Sep 14;59(74):11129-11132. doi: 10.1039/d3cc03508e.

Authors

Mai Nagase^{1

2}, Sachiko Nakano¹, Yasutomo Segawa^{1

2}

Affiliations

¹ Institute for Molecular Science, Myodaiji, Okazaki, 444-8787, Japan. segawa@ims.ac.jp.
² The Graduate University for Advanced Studies, SOKENDAI, Myodaiji, Okazaki, 444-8787, Japan.

PMID: 37647017
DOI: 10.1039/d3cc03508e

Abstract

Penta- and hexa(3,4-thienylene)s were synthesized as a potential precursor for thiophene-containing polyarenes, and the structures were determined via X-ray crystallography. The interconversion of thiophene rings is fast in penta(3,4-thienylene), and slow in hexa(3,4-thienylene) reflecting the activation energy for enantiomerization. Size-dependent bathochromic shifts were observed in UV-vis absorption spectra.