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Investigations on photochromic properties of 2,6-bis(5-bromo-2-hydroxybenzylidene)cyclohexanone

Abstract

The network of chemical reactions of 2,6-bis(5-bromo-2-hydroxybenzylidene)cyclohexanone (BHBC) when submitted to light and different pH values has been investigated. The pH dependent species involved in the chemical network have been identified and characterized by NMR and UV-VIS spectroscopy. Direct pH jumps were carried out by adding strong acid to equilibrated solutions of trans-chalcone (Ct) forming the flavylium cation which was stable only at extremely acidic conditions (pH < 0.5). The single crystal X-ray study and NMR analysis has confirmed the structure of new flavylium cation. In the case of reverse pH jump, the Ct species interconverted instantaneously into deprotonated trans-chalcone (Ct2-) around pH 12. A new colorless compound 3,11-dibromo-7,8-dihydro-6H-chromeno[3,2-d]xanthenes (B-B) isolated from the equilibrated solution of trans-chalcone species in methanol after long periods of time (100 h) in dark conditions have been isolated and fully characterized by NMR and X-ray diffraction. The rate of the reaction increased when the solution of trans-chalcone was exposed to light and total conversion of Ct into spiropyran-like compound (B-B) was achieved in about 30 minutes. The B-B form was stable in neutral and basic conditions, while at low pH values it converts into cationic form AH+.

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Publication details

The article was received on 21 Dec 2016, accepted on 05 Apr 2017 and first published on 06 Apr 2017


Article type: Paper
DOI: 10.1039/C6PP00466K
Citation: Photochem. Photobiol. Sci., 2017, Accepted Manuscript
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    Investigations on photochromic properties of 2,6-bis(5-bromo-2-hydroxybenzylidene)cyclohexanone

    L. Corici, S. Sova, V. Badea, D. Aparaschivei, O. Costisor and L. Cseh, Photochem. Photobiol. Sci., 2017, Accepted Manuscript , DOI: 10.1039/C6PP00466K

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