Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 3, Pages 1487-1498Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b02685
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Funding
- National Science Centre Poland [UMO-2015/19/B/ST5/02917]
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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.
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