Issue 99, 2014

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
13 Jul 2014
Accepted
23 Oct 2014
First published
23 Oct 2014
This article is Open Access
Creative Commons BY license

RSC Adv., 2014,4, 56003-56012

Author version available

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

A. Wrona-Piotrowicz, J. Zakrzewski, R. Métivier, A. Brosseau, A. Makal and K. Woźniak, RSC Adv., 2014, 4, 56003 DOI: 10.1039/C4RA07045C

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