Aliphatic Amine Discrimination by Pentafluorophenyl Dibromo BODIPY

Abstract

Two new fluorescent BODIPY dyes have been designed and synthesized. They dyes differ in their meso substituents, which have different electronic properties. Their selective reactivity towards an Ar-S(N)2 reaction has been explored as a potential basis for colorimetric and fluorescent discrimination of primary, secondary and tertiary aliphatic amines. This dual-mode, instantaneous recognition event is unprecedented.

Thiocyanation of BODIPY dyes and their conversion to thioalkylated derivatives

“…[28][29][30][31] Moreover, in general, 3-amino BODIPYs show solvatochromic behavior with a broad red-shifted emission and a blue-shifted absorption. 28,[32][33][34][35][36] Similarly, we observed that the addition of the piperidinyl group by itself (compound 10) diminished the quantum yields and drastically changed the shapes of the absorption and emission bands, significantly broadening them. These effects were also observed for 18 and were highly influenced by solvent polarity (Fig.…”

Synthesis and Unique Optical Properties of Selenophenyl BODIPYs and Their Linear Oligomers

“…A 5 mL two-neck flask was charged with 4 (50.6 mg, 108 μmol), 2-selenopheneboronic acid (41.2 mg, 236 μmol), cesium carbonate (141 mg, 431 μmol), tri- tert -butylphosphonium tetrafluoroborate (12.5 mg, 43.1 μmol), tris­(di­benzyl­idene­acetone)­dipalladium(0) (10.0 mg, 10.9 μmol), dry THF (5.0 mL), and deaerated water (50 μL). The mixture was stirred for 8 h at ambient temperature under an argon atmosphere in a dark condition.…”

“…Synthesis of the BODIPY monomers is shown in Scheme . SB1a and SB1b were synthesized from 3,5-dibromo BODIPY 4 and 5 , respectively, by the Suzuki–Miyaura cross-coupling reaction with 2-selenenopheneboronic acid. SB1c was similarly obtained from 2,6-dibromo BODIPY 6 .…”

BODIPY derivatives modified with carborane clusters: synthesis, characterization and DFT studies

“…For the preparation of carborane-substituted BODIPYs, 3,5-dibromo-8-pentafluorophenyl-BODIPY ( 1 ) prepared according to a reported procedure 41 was used as the starting compound. The BODIPY core in this compound can be easily modified with the desired functionalities by the modification of pyrrole rings via bromo substitution with a variety of nucleophiles 42,43 as well as through the nucleophilic S N 2 substitution of the para -fluorine atom in the C 6 F 5 substituent.…”