Thiocyanation of BODIPY dyes and their conversion to thioalkylated derivatives

被引：13

作者：

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
]}

机构：

[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

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 21期

基金：

巴西圣保罗研究基金会;

关键词：

BORON-DIPYRROMETHENE; ARYL THIOCYANATES; NUCLEOPHILIC-SUBSTITUTION; SPECTROSCOPIC PROPERTIES; PHOTOPHYSICAL PROPERTIES; HETEROAROMATIC-COMPOUNDS; OPTICAL-PROPERTIES; ENERGY-TRANSFER; FUNCTIONALIZATION; PROBE;

D O I：

10.1039/c5ob00499c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：6031 / 6038

页数：8

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