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Royal Society of Chemistry, RSC Advances, 99(4), p. 56003-56012, 2014

DOI: 10.1039/c4ra07045c

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Efficient synthesis of pyrene-1-carbothioamides and carboxamides. Tunable solid-state fluorescence of pyrene-1-carboxamides

This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

Pyrene reacts with potassium thiocyanate and organic isothiocyanates in the presence of trifluoromethanesulfonic acid to afford primary and secondary pyrene-1-carbothioamides in high yields. These compounds were efficiently oxidatively desulfurized with Oxone® to the corresponding carboxamides. The amides display solid-state fluorescence with quantum efficiencies up to 62%, originating from monomers, aggregates (such as preformed dimers), and/or excimers, depending on the substituent at the nitrogen atom. Single crystal X-ray diffraction characterization of one highly emissive compound supports this assumption. ; Publikacja w ramach programu Royal Society of Chemistry "Gold for Gold" 2014 finansowanego przez Uniwersytet Łódzki.