Synthesis, Characterization and Evaluation of a Novel BODIPY Derivative as a Colorimetric Chemosensor for Fe3+ Recognition

Abstract

A 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) derivative functionalized with a formyl group at position 2 was synthesized in 57% yield. The compound was characterized by 1 H and 13 C Nuclear Magnetic Resonance (NMR) spectroscopy and mass spectrometry. The photophysical characterization was carried out by means of absorption and fluorescence spectroscopies in acetonitrile solutions. The BODIPY derivative showed an absorption band at 492 nm and an emission band at 506 nm. A preliminary evaluation of the recognition ability of the BODIPY derivative was investigated in the presence of several cations with environmental and biomedical relevance. A highly selective colorimetric response was obtained for Fe 3+ .

A BODIPY Derivative for Selective Fluorescent Chemosensing of Iron (III)

“…Considering the above-mentioned facts as well as our research interest in BODIPY derivatives for several applications [8][9][10][11][12][13][14][15], particularly as optical chemosensors, we report herein a BODIPY fluorophore functionalized with a phenyl group at the meso-position for a selective response towards Fe 3+ . The chemosensory ability of the BODIPY derivative was investigated in acetonitrile in the presence of different ions, showing a selective fluorescence quenching upon Fe 3+ interaction.…”

Anion Colorimetric Chemosensor Based on a Benzimidazole-Functionalized BODIPY Derivative

“…Among chemosensors based on organic molecules, BODIPY is a multifaceted signaling scaffold that displays notable photophysical properties, such as sharp absorption and emission patterns, a high molar extinction coefficient, high fluorescence quantum yield and good photostability under physiological conditions. The BODIPY core can be modified through chemical functionalization to modulate its photophysical properties and to introduce selective recognition sites for a higher target binding affinity [5][6][7][8][9][10][11][12][13][14][15]. Moreover, (benz)imidazole and its derivatives have been investigated as anion and cation recognition systems that exhibit optical changes upon analyte complexation [16][17][18][19][20][21][22].…”

“…As an extension of the work developed in our research group concerning heterocyclic chromofluorogenic sensors [10,12,13,16,20,21], we report the synthesis and characterization of a BODIPY functionalized with an anthracene group at the meso position and a benzimidazole group at position 2, for a selective colorimetric response towards a hydrogen sulfate anion (HSO 4 − ). The recognition behavior of the BODIPY derivative was studied in an solution of acetonitrile/water (75:25) in the presence of different anions, and the results showed a specific color change of the solution upon HSO 4 − complexation.…”

Synthesis, Characterization and Evaluation of a Carbazolyl-BODIPY as a Fluorimetric Chemosensor for F-

“…In continuation of the work developed in our research group [6][7][8][9][10][11][12], regarding the synthesis and evaluation of the optoelectronic properties of BODIPY derivatives for several applications, namely, as chromofluorogenic chemosensors, we report the synthesis, spectroscopic characterization, and evaluation of the chemosensory ability of a novel BODIPY derivative functionalized with a carbazolyl group at the meso position as a fluorimetric chemosensor for the selective detection of fluoride.…”