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Effect of different substituents of methyl 5-R-salicylates on excited state intramolecular proton transfer process

Abstract

The proton transfer reaction in Methyl 5-R-salicylate is found to be highly sensitive to the presence of specific substituents in resonance with the hydroxyl group, leading to different fluorescent behavior of the Methyl 5-R-salicylate with different substituents (J. Phys. Chem. B 2015, 119, 2132). But the detailed survey to its reaction mechanism is lacking. In our research, the hydrogen bond strengthening behavior in excited states is affected by the different substituents that have been reported for the first time. Absorption and emission spectra calculated for the work presented here agree well with experimental results. At the same time, in order to provide a reliable description of the reaction energy profiles, we compare the barrier differences obtained by CAM-B3LYP and B3LYP methods, and we visually observe the effect of different substituents on the ESIPT reactions in Methyl 5-R-salicylates by combining the potential energy curves. So the excited state intramolecular proton transfer (ESIPT) reactions in Methyl 5-R-salicylates molecules are detailedly investigated by density functional theory (DFT) and time dependent density functional theory (TDDFT) methods. It can be confirmed that the mobility of the intramolecular π electrons is affected as increasing in the resonant strength of the different substituents and hydroxyl groups. As a consequence, the hydrogen bond interaction gradual weakening mechanism has been perfectly verified, that is, the ESIPT reaction is more difficult to occur from MS → 5MeMS → 5FMS → 5ClMS → 5BrMS → 5MeOMS → 5AmMS molecules.

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Publication details

The article was received on 13 Oct 2017, accepted on 22 Dec 2017 and first published on 22 Dec 2017


Article type: Paper
DOI: 10.1039/C7CP06987A
Citation: Phys. Chem. Chem. Phys., 2017, Accepted Manuscript
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    Effect of different substituents of methyl 5-R-salicylates on excited state intramolecular proton transfer process

    Y. Li, Y. Ma, Y. Yang, W. Shi, R. Lan and Q. Guo, Phys. Chem. Chem. Phys., 2017, Accepted Manuscript , DOI: 10.1039/C7CP06987A

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