title: Thiocyanation of BODIPY dyes and their conversion to thioalkylated derivatives.
abstract: 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.
authors.affiliation: Departamento de Ciências Farmacêuticas, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, SP, Brazil. flavioemery@fcfrp.usp.br.
authors.forename: Lucas Cunha Dias
authors.initials: LC
authors.lastname: de Rezende
authors.forename: Shaiani Maria Gil
authors.initials: SM
authors.lastname: de Melo
authors.forename: Stijn
authors.initials: S
authors.lastname: Boodts
authors.forename: Bram
authors.initials: B
authors.lastname: Verbelen
authors.forename: Wim
authors.initials: W
authors.lastname: Dehaen
authors.forename: Flavio
authors.initials: F
authors.lastname: da Silva Emery
mesh_terms: D000478:Alkylation; D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D013861:Thiocyanates / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D005456:Fluorescent Dyes; D013861:Thiocyanates