Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 19, Pages 13774-13782Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01459
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Funding
- FWO [G0F6619N]
- KU Leuven [C14/19/078]
- Research Foundation-Flanders (FWO) [1SC4719N]
- Hercules Foundation of the Flemish Government [20100225-7]
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This study explored the potential of 1,2,3-triazolium salts for the formation of water-soluble chromophores. The synthesis of water-soluble 1,2,3-triazolium BOPAHY dyes was achieved by a metal-free pathway.
Water-soluble BOPAHY fluorophores have not yet been reported. The potential of 1,2,3-triazolium salts for the formation of water-soluble chromophores is explored. 1,2,3-Triazole-substituted pyrroles were synthesized in a metal-free pathway and alkylated to obtain water-soluble 1,2,3-triazolium BOPAHY dyes. High fluorescence quantum yields were observed for triazole-bridged BOPAHY dyes in DCM and moderate fluorescence quantum yields for 1,2,3-triazolium-bridged BOPAHY chromophores in DCM and water. The fluorescence of the freely rotatable 1,2,3-triazolium-linked BOPAHYs is partially quenched in water.
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