A meso-Triphenylamine-BODIPY Derivative for the Optical Chemosensing of Metal Ions

Abstract

The design and synthesis of organic molecules for recognition of biologically/environmentally important metal ions have been emerging as a highly regarded research field. BODIPY core is a versatile signaling molecule that can be fine-tuned with functional groups to create selective binding sites and improve its optical properties. As an extension of the work developed in our research group, we report the synthesis and characterization of a BODIPY functionalized with triphenylamino and a formyl group at meso and 2-position, respectively, for a highly selective detection of Cu 2+ and Fe 3+. The preliminary study of the BODIPY derivative as optical chemosensor was carried out in acetonitrile solution in the presence of different cations and interaction with Cu 2+ and Fe 3+ induced a perceptible color change. UV-visible titrations showed changes in the absorption spectra upon addition of 3 equivalents of each cation with the appearance of a new absorption band at 693 nm.

Colorimetric Chemosensor for Cu2+ and Fe3+ Based on a meso-Triphenylamine-BODIPY Derivative

“…All commercial reagents and solvents were used as received. BODIPY 1 was previously synthesized by our research group [ 31 , 32 ].…”

Anion Dual Mode Fluoro-Chromogenic Chemosensor Based on a BODIPY Core

“…As an extension of the work developed in our research group [7][8][9][10][11], we report a BODIPY derivative bearing a phenyl group at the meso position and a formyl group at position 2 of the BODIPY core for the simultaneous colorimetric and fluorimetric detection of CN − and F − . The recognition behavior of the BODIPY derivative was studied in an aprotic solvent (acetonitrile) in the presence of different anions, and the UV-vis and fluorescence spectroscopic titrations demonstrated a decrease in the absorption band intensity and a fluorescence quenching upon interaction with CN − and F − .…”

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.…”