Thiocyanation of BODIPY dyes and their conversion to thioalkylated derivatives

Author(s)

Dias de Rezende, Lucas Cunha ^{[1, 2]} ; Gil de Melo, Shaiani Maria ^[1] ; Boodts, Stijn ^[2] ; Verbelen, Bram ^[2] ; Dehaen, Wim ^[2] ; Emery, Flavio da Silva ^[1]

Affiliation

^[1] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, Dept Ciencias Farmaceut, BR-14049 Ribeirao Preto, SP - Brazil

^[2] Katholieke Univ Leuven, Dept Chem, B-3001 Leuven - Belgium

• Document type: Journal article
• Source: ORGANIC & BIOMOLECULAR CHEMISTRY; v. 13, n. 21, p. 6031-6038, 2015.
• Web of Science Citations: 5

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. (AU)

• FAPESP's process: 13/24408-9 - Chemical modification of BODIPY fluorophores aiming at structural and photophysical diversity for the development of novel fluorescent probes
• Grantee: Lucas Cunha Dias de Rezende
• Support Opportunities: Scholarships abroad - Research Internship - Doctorate
• FAPESP's process: 11/23342-9 - Synthesis, characterization and applications of BODIPY fluorophores.
• Grantee: Lucas Cunha Dias de Rezende
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 12/20990-2 - Antiinfective compounds: an evolution in the medicinal chemistry of leishmanicidal tiazoles and the search for new tuberculostic agents
• Grantee: Flavio da Silva Emery
• Support Opportunities: Regular Research Grants