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DOI: 10.1055/s-0036-1588592
Facile Synthesis of Thiacalix[n]thiophene Derivatives
Publikationsverlauf
Received: 26. Juli 2016
Accepted after revision: 22. August 2016
Publikationsdatum:
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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