Issue 6, 2018

β-Diketone derivatives: influence of the chelating group on the photophysical and mechanofluorochromic properties

Abstract

A diphenyl-boron β-diketonate complex was synthesized. Its photophysical properties were studied in solution and in the solid-state, and compared to those of its parent diketone and the corresponding difluoro-boron complex. TD-DFT calculations show that the molecular orbitals involved in the first Franck–Condon transition are very different for the three compounds studied. The difluoro-boron complex is strongly fluorescent in solution, and remains fluorescent in the solid-state. The free diketone turns to be very weakly fluorescent in solution and displays significant Aggregation Induced Enhanced Emission (AIEE) in the crystalline state, which can be explained by a rigidification of the molecule, while the diphenyl-boron complex is weakly fluorescent in solution as well as in the solid-state. For the free diketone and the difluoro-boron complex a mechanofluorochromic response is observed upon grinding the crystalline powder in a mortar, while for the diphenyl-boron complex no fluorescence emission change is detected under these conditions. Overall, this study shows that the nature of the chelating group has a crucial influence on the photophysical and mechanofluorochromic properties of β-diketonate complexes, leading to a wide variety of behaviors within the closely related structures of such derivatives.

Graphical abstract: β-Diketone derivatives: influence of the chelating group on the photophysical and mechanofluorochromic properties

Supplementary files

Article information

Article type
Paper
Submitted
15 Feb 2018
Accepted
03 Mai 2018
First published
11 Mai 2018

Photochem. Photobiol. Sci., 2018,17, 822-828

β-Diketone derivatives: influence of the chelating group on the photophysical and mechanofluorochromic properties

M. Louis, R. Guillot, R. Métivier and C. Allain, Photochem. Photobiol. Sci., 2018, 17, 822 DOI: 10.1039/C8PP00070K

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