Synlett 2016; 27(17): 2407-2415
DOI: 10.1055/s-0036-1588592
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© Georg Thieme Verlag Stuttgart · New York

Facile Synthesis of Thiacalix[n]thiophene Derivatives

Masashi Hasegawa*
,
Ryota Inoue
,
Yasuhiro Mazaki
Further Information

Publication History

Received: 26 July 2016

Accepted after revision: 22 August 2016

Publication Date:
05 September 2016 (online)

Dedicated to Prof. Dr. Masahiko Iyoda on the occasion of his 70th birthday

Abstract

Recently, we reported a new synthetic approach toward a ­series of thiacalix[n]thiophene and thiacalix[n]dithienothiophene derivatives, cyclic homologues of sulfur-bridged cyclic oligothiophenes. A palladium-catalyzed coupling reaction of stannyl sulfide (Bu3Sn)2S and dibromothiophene/dibromodithienothiophene derivatives gave the corresponding macrocycles in good yield. Substituents at the β-position can play a key role in effective cyclization. This paper also summarizes the molecular and electronic structures of the novel macrocycles. Unlike conventional calixarenes, they exhibit distinct electron-donating properties. Furthermore, self-assembly and host–guest properties, leading to supramolecular structures, are also briefly discussed.

 
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