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

Abstract

A diphenyl-boron β-diketonate complex has been synthesized. Its photophysical properties have been studied in solution and in the solid-state, and compared to those of the parent diketone and of the corresponding difluoro-boron complex. TD-DFT calculations show that the molecular orbitals involved in the first Franck-Condon transition are vey different for the three compounds studied. The difluoro-boron complex is strongly fluorescent in solution, and remains fluorescent in 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 mechanofluochromic properties of β-diketonate complexes, leading to a wide variety of behaviors within the closely related structures of such derivatives.

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Publication details

The article was received on 15 Feb 2018, accepted on 03 May 2018 and first published on 11 May 2018


Article type: Paper
DOI: 10.1039/C8PP00070K
Citation: Photochem. Photobiol. Sci., 2018, Accepted Manuscript
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    β-Diketone derivatives: influence of the chelating group on the photophysical and mechanofluorochromic properties

    M. Louis, R. Guillot, R. Metivier and C. Allain, Photochem. Photobiol. Sci., 2018, Accepted Manuscript , DOI: 10.1039/C8PP00070K

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