Functionalisation of fluorescent BODIPY dyes by nucleophilic substitution

Abstract

The BODIPY chromophore can be easily modified by nucleophilic mono- or disubstitution of 3,5-dichloroBODIPY with O-, N-, S- and C-nucleophiles. Absorption and fluorescence spectral data of the new BODIPY derivatives are also reported.

Substituent Effects at the 5-Position of 3-[Bis(pyridine-2-ylmethyl)amino]-BODIPY Cation Sensor Used for Ratiometric Quantification of Cu2+

“…In the second step, we introduced DPA as the cation recognition moiety at the 3-position of each BODIPY by aromatic nucleophilic substitution. 25 This recognition moiety has an especially high affinity for Table 1 shows the yield of the first and the second steps in the synthesis. The sulfonylphenyl-substituted BODIPY 1a was obtained in good yield (75% in the first step and 80% 4 in the second step).…”

A fluorometric paper-based sensor array for the discrimination of heavy-metal ions

“…We constructed BODIPY-based indicators from readily available building blocks of 3,5-dichloroBODIPY and multi-pyridyl receptors following the elegant method of Dehaen [31,32]. A single chlorine of 3,5-dichloroBODIPY could be replaced with different substituents by carefully tuning the reaction conditions, as shown in Scheme 1.…”

BODIPY-based fluorometric sensor array for the highly sensitive identification of heavy-metal ions

“…We constructed BODIPY-based indicators from readily available building blocks of 3,5-dichloroBODIPY and multi-pyridyl receptors following the elegant method of Dehaen (Scheme 1) [41,42]. A single chlorine of 3,5-dichloroBODIPY could be replaced with different substituents by carefully tuning the reaction conditions.…”