title: Use of Stable Amine-Capped Polyynes in the Regioselective Synthesis of Push-Pull Thiophenes.
abstract: The reactions of a series of 1-halopolyynes with secondary amines led to novel amine end-capped polyynes exhibiting surprisingly high stability toward moisture. The new compounds were characterized by NMR spectroscopy, ESI-MS spectrometry, and X-ray single-crystal diffractometry. The use of amine end-capped polyynes as precursors to substituted push-pull thiophenes was next presented. The results show the first-to the best of our knowledge-transformation of ynamine to thiophene and the first regioselective transformation of a longer polyynes to butadiyne-substituted thiophene. Photophysical studies of the resulting compounds show that some of the substituted thiophenes have high quantum yield photoluminescence upon UV light irradiation.
authors.affiliation: Department of Chemistry, University of Wrocław , 14 F. Joliot-Curie, 50-383 Wrocław, Poland.
authors.forename: Bartłomiej
authors.initials: B
authors.lastname: Pigulski
authors.affiliation: Department of Chemistry, University of Wrocław , 14 F. Joliot-Curie, 50-383 Wrocław, Poland.
authors.forename: Patrycja
authors.initials: P
authors.lastname: Męcik
authors.affiliation: Department of Chemistry, University of Wrocław , 14 F. Joliot-Curie, 50-383 Wrocław, Poland.
authors.forename: Jakub
authors.initials: J
authors.lastname: Cichos
authors.affiliation: Department of Chemistry, University of Wrocław , 14 F. Joliot-Curie, 50-383 Wrocław, Poland.
authors.forename: Sławomir
authors.identifier: 0000-0002-0570-8847
authors.initials: S
authors.lastname: Szafert