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Use of stable amine-capped polyynes in the regioselective synthesis of push-pull thiophenes.
Autorzy
Rok wydania
2017
Czasopismo
Numer woluminu
82
Strony
1487-1498
DOI
10.1021/acs.joc.6b02685
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
The reactions of a series of 1-halopolyynes with secondary amines led to novel amine end-capped polyynes exhibiting surprisingly high stability towards 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.
Adres publiczny
http://dx.doi.org/10.1021/acs.joc.6b02685
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