Open AccessThiocyanation of BODIPY dyes and their conversion to thioalkylated derivatives
Author(s) -
Lucas Cunha Dias de Rezende,
Shaiani Maria Gil de Melo,
Stijn Boodts,
Bram Verbelen,
Wim Dehaen,
Flávio da Silva Emery
Publication year - 2015
Publication title -
organic and biomolecular chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.923
H-Index - 146
eISSN - 1477-0539
pISSN - 1477-0520
DOI - 10.1039/c5ob00499c
Subject(s) - bodipy , chemistry , combinatorial chemistry , photochemistry , fluorescence , physics , quantum mechanics
A high-yielding method for the direct thiocyanation of BODIPY dyes is described. In 1,3-dimethyl BODIPYs, the thiocyanato group adds at position 2, whereas the insertion occurs at position 5 in 3-amino BODIPYs. The transformation of the thiocyanato group enables the synthesis of thioalkylated BODIPYs. 2-Thioalkylated BODIPYs and 3-thiocyanato-5-piperidino BODIPYs exhibit interesting spectroscopical features. Hence, the described synthetic methodology can be used for the photophysical tuning of BODIPY dyes.
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