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Theoretical research on excited-state intramolecular proton coupled charge transfer modulated by molecular structure.

ABSTRACT: At the TD-B3LYP/TZVP/IEFPCM theory level, we have theoretically studied the excited-state intramolecular proton coupled charge transfer (ESIPCCT) process for both 4'-N,N-diethylamino-3-hydroxyflavone (3HFN) and 2-{[2-(2-hydroxyphenyl)benzo[d]oxazol-6-yl]methylene}malononitrile (diCN-HBO) molecules. Our calculated hydrogen bond lengths and angles sufficiently confirm that the intramolecular hydrogen bonds O₁-H₁⋯O₂ and O₁-H₁⋯N₁ formed at the S₀ states of 3HFN and diCN-HBO should be significantly strengthened in the S₁ state, which is further supported by the results obtained based on the analyses of infrared spectra shifts, molecular orbitals and charge density differences maps. The significant strengthening of intramolecular hydrogen bonds O₁-H₁⋯O₂ and O₁-H₁⋯N₁ upon photoexcitation should facilitate the ESIPCCT process of the two title molecules. The scanned potential energy curves and confirmed excited-state transition states for both 3HFN and diCN-HBO show that the proton can be easily transferred from O₁ to O₂ (N₁ for diCN-HBO) through the strengthened intramolecular hydrogen bonds upon photoexcitation to the S₁ state.

SUBMITTER: Yang D

PROVIDER: S-EPMC9085251 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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Theoretical research on excited-state intramolecular proton coupled charge transfer modulated by molecular structure.

Yang Dapeng D Yang Guang G Jia Min M Song Xiaoyan X Zhang Qiaoli Q Zhang Tianjie T Gao Haiyan H

RSC advances 20180821 52

At the TD-B3LYP/TZVP/IEFPCM theory level, we have theoretically studied the excited-state intramolecular proton coupled charge transfer (ESIPCCT) process for both 4'-N,N-diethylamino-3-hydroxyflavone (3HFN) and 2-{[2-(2-hydroxyphenyl)benzo[d]oxazol-6-yl]methylene}malononitrile (diCN-HBO) molecules. Our calculated hydrogen bond lengths and angles sufficiently confirm that the intramolecular hydrogen bonds O1-H1⋯O2 and O1-H1</su ...[more]

PMID: 35547296

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Project description:Considering the applications of fluorescent probes and the information they provide, their brightness of fluorescence and photostability are of paramount importance. However, in the case of steady-state fluorescence spectroscopy and fluorescence microscopy, the amount of information can be increased by the application of multi-channel probes, via a multi-band fluorophore introduced in the probe molecule. In most cases, the use of such a multi-band (or multi-channel) fluorophore can also be combined with the concomitant introduction of one or several analyte receptors. Most often, the design of ratiometric probes with multi-band fluorescence emission are based on phenomena such as photoinduced intramolecular charge transfer (ICT) or excited state intramolecular proton transfer (ESIPT). Although ICT probes were up to recently the most popular, ESIPT probes and among them 3-hydroxyflavone derivatives, were shown to be the most productive. Several general problems were resolved by this family of probes, as for example the measurement of local dielectric constant, local H-bond accepting ability, water local concentration and ATP concentration in small volumes. Incorporation of such multi-channel probes into lipid membranes allowed to measure the different membrane potentials and to detect cell apoptosis. Also, it enabled to recognize and characterize the rafts formation in different lipid bilayers and peculiar features of the charged membrane interface. Such probes are also able to provide a concentration-dependent fluorescence signals upon binding of H+, Mg2+and Ba2+ions, and thus to recognize these different cations. The multi-channel probes are effective tools in the study of interactions of macromolecules such as peptides, proteins and nucleic acids. The most useful feature is that they inform simultaneously about several physical parameters, in this way giving a better insight in the investigated system. Thus, by comparing the reviewed probes with other modern fluorescent approaches, it can be concluded they are more informative and accurate tools.

Dataset Information

Theoretical research on excited-state intramolecular proton coupled charge transfer modulated by molecular structure.

Publications

Theoretical research on excited-state intramolecular proton coupled charge transfer modulated by molecular structure.

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