Concise synthesis of oligo(thienylene-vinylene) with a head-to-tail type structure is achieved by regioselective deprotonative coupling of 3-hexylthiophene. The palladium catalyzed reaction of 3-hexylthiophene with (E)-2-(2-bromoethenyl)-3-hexylthiophene takes place to afford head-to-tail type trans-1,2-dithienylethene. Further extension of a vinylthiophene unit is similarly performed in an iterative manner.
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[All]-S,S-dioxide Oligo-Thienylenevinylenes: Synthesis and Structural/Electronic Shapes from Their Molecular Force Fields.
Chemistry
January 2019
School of Chemistry, Tel Aviv University, 69978, Tel Aviv, Israel.
Oligo-S,S-dioxothienylenevinylenes have been prepared by transferring oxygen atoms to the sulfur atoms using the HOF⋅CH CN complex. Their photophysical properties are presented in comparison with their thiophenevinylene congeners. Together with their vibrational properties and molecular force fields, this study allows for the interpretation of the alteration of aromaticity and inter-ring exocyclic π-conjugation in this series.
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