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Issue 109, 2015
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Unusual spectroscopic and photophysical properties of meso-tert-butylBODIPY in comparison to related alkylated BODIPY dyes

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Abstract

Five alkyl-substituted difluoroboron dipyrrin (BODIPY) dyes have been synthesized: three with a methyl, isopropyl or tert-butyl group at the meso-position of the BODIPY core and two substituted with one or two tert-butyl functions at the 3/5-positions. X-Ray structural analysis, UV-vis absorption spectroscopy and fluorescence (steady-state and time-resolved) techniques have been used to study the structures and the spectroscopic/photophysical properties of these dyes. All but one of these BODIPYs are highly fluorescent in all the solvents tested, the exception being meso-tert-butylBODIPY (2). Derivative 2 differs from the other alkylated boron dipyrrins as it exhibits a broad and red-shifted fluorescence band with a large Stokes shift. In addition, very low fluorescence quantum yields and short fluorescence lifetimes characterize 2. Quantum chemical calculations indicate that 2 has a distorted, nonplanar geometry in the S1 excited state due to the rotation of 8-tert-butyl group. Our results lead us to the conclusion that the torsional rotation about the bond connecting the meso-C and the quarternary C of the tert-butyl group of 2 plays a crucial role in the fast radiationless deactivation of this isomer.

Graphical abstract: Unusual spectroscopic and photophysical properties of meso-tert-butylBODIPY in comparison to related alkylated BODIPY dyes

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Publication details

The article was received on 28 Aug 2015, accepted on 12 Oct 2015 and first published on 12 Oct 2015


Article type: Paper
DOI: 10.1039/C5RA17419H
Author version available: Download Author version (PDF)
Citation: RSC Adv., 2015,5, 89375-89388
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    Unusual spectroscopic and photophysical properties of meso-tert-butylBODIPY in comparison to related alkylated BODIPY dyes

    L. Jiao, C. Yu, J. Wang, E. A. Briggs, N. A. Besley, D. Robinson, M. J. Ruedas-Rama, A. Orte, L. Crovetto, E. M. Talavera, J. M. Alvarez-Pez, M. Van der Auweraer and N. Boens, RSC Adv., 2015, 5, 89375
    DOI: 10.1039/C5RA17419H

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