Expanded Bodipy Dyes: Anion Sensing Using a Bodipy Analog with an Additional Difluoroboron Bridge

Abstract

Oxalyl-tethered pyrroles can be doubly bridged with two difluoroboron chelating units to yield bright orange dyes. Interestingly, in polar organic solvents, the addition of fluoride and cyanide result in reversible detachment of the otherwise stable difluoroboron bridges, resulting in sharp changes in color. Thus, this novel compound behaves as a highly selective chromogenic sensor for fluoride and cyanide ions.

A turn-on fluorescence chemosensor for Al3+, F− and CN− ions, and its application in cell imaging

“…But a few bifunctional chemosensors can selectively detect Al 3+ and CN -, [27,28] Al 3+ and F -, [29,30] and F -and CN - [31,32] simultaneously. The development of single molecular sensors for multi-ions has become a challenge.…”

“…[40,41] While among the binding mechanisms for CN -, such as coordination, hydrogen-bonding interactions, and nucleophilic addition reactions, reaction-based sensors show both high selectivity and sensitivity. [32,[42][43][44] As eported, the Schiff base (-HC=N-) was used as binding site to detect CN -through a nucleophilic addition reaction. [45,46] Herein, we designed and synthesized a new Schiff base 3-[(2-hydroxybenzylidene)-amino]-1H-pyridin-2-one (HL) as a fluorescence chemosensor for multi-ions.…”

A theoretical and experimental NMR study of BODIPY 493/503: difluoro{2‐[1‐(3,5‐dimethyl‐2H‐pyrrol‐2‐ylidene‐N)ethyl]‐3,5‐dimethyl‐1H‐pyrrolato‐N}boron

“…[1] Other applications of these dyes are related to fluorescent probes, [2][3][4] deep-red lighting sources, [5] bioactive CO-releasing molecules [6] and solar cells, [7] amongst many others. [8][9][10] Concerning BODIPY NMR properties, there are several compounds with reported data (Scheme 1) especially related to [11] ; 4, 1 J 11B19F = 33.4 Hz [12] ; 5, 11 B = 0.28, 1 J 11B19F = 28.7 Hz [13] ; 6, 11 B = 0. 41,19 F = À150.6 [14] ; 7-(rac), [ 16] Results and discussion were recorded in CDCl 3 .…”

Design and Synthesis of Some Imidazolyl Derivatives: Photophysical Studies and Application in the Detection of Anions

“…Some novel receptor system based on boron [30,31] and silicon [32] derivatives, quantum dots [33], mesoporous silica material [7 -12], and BODIPY [34] have been successfully utilized to detect anions by hydrogen bonding [35 -39], coordination or covalent bonding interactions [40 -42]. Similarly, ensemble based demetallization of copper by cyanide has also been utilized to detect cyanide-displacement approach [15 -17].…”