Time-Dependent Density Functional Theory Study on a Fluorescent Chemosensor Based on C–H•••F Hydrogen-Bond Interaction

Li, Guangyue

doi:10.4208/cicc.2013.v1.n1.9

Cited by 44 publications

(12 citation statements)

References 32 publications

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“…The photophysical properties and geometries of these chemosensors can be inferred from the measured 1 H NMR spectra, time-resolved absorption spectra and fluorescence spectra in the study of the Si-O bond cleavage, ICT and ESPT processes [2,13]. As a complement to the experimental techniques, the density functional theory (DFT)/time-dependent functional theory (TD-DFT) methods are also suitable for studying the ICT, ESPT and photoinduced electron transfer processes by presenting direct and detailed information on geometries and other properties of chemosensors [16,[21][22][23][24][25][26].…”

Section: Introductionmentioning

confidence: 99%

Intramolecular charge transfer and sensing mechanism for a colorimetric fluoride sensor based on 1,8-naphthalimide derivatives

et al. 2013

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The sensing mechanism of a fluoride colorimetric chemosensor 4-(tert-butyldimethylsilyloxy)-Nbutyl-naphthalimide has been studied with density functional theory and time-dependent density functional theory methods. The theoretical results suggest that the low barrier of the desilylation reaction is responsible for the rapid response speed to the fluoride anion of the chemosensor. The calculated vertical excitation energies in the ground state of the chemosensor and its desilylation product agree well with the experimental UV-Vis absorbance spectra. It is also found that the intramolecular charge transfer process of the first excited state of the desilylation product induces the redshift of the absorbance and fluorescence spectra of the desilylation product compared with that of the chemosensor. Further, the previously experimentally incorrect assignment of the 1 H NMR spectrum of the desilylation product has been rectified in the present theoretical study.

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Section: Introductionmentioning

confidence: 99%

Intramolecular charge transfer and sensing mechanism for a colorimetric fluoride sensor based on 1,8-naphthalimide derivatives

et al. 2013

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“…Another is that HOCl does not exist in lysosomes, because this organelle does not generate HOCl and the HOCl flux from phagosomes might be eliminated by the reducing substances within the cytoplasm before it reaches lysosomes. In order to study the mechanism of the lysosome-targetable fluorescent probe for HOCl, the further theoretical calculations will be needed [47][48][49][50].…”

Section: Fluorescence Imaging Of Endogenous Hocl In Raw2647 Cellsmentioning

confidence: 99%

Development of a selenide-based fluorescent probe for imaging hypochlorous acid in lysosomes

Ding

Zhao

et al. 2015

Journal of Photochemistry and Photobiology A: Chemistry

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“…As given in Figure 1c, the energy keeps rising as H2 approaches O2 which indicates the absence of GSPT from this site. As hydrogen bonds affect not only the GSPT processes but also the ESPT processes, [20][21][22][23][24][25][26][36][37][38][39][40] the hydrogen-bonding pattern in the S 1 state is investigated. As shown in Figure 1b, the S 1 state basic model has a very weak hydrogen bond with the bond length of 3.115 Å and the bonding energy…”

Section: Ph-related Quenching Mechanism Of Fpt and The Proton-transfementioning

confidence: 99%

pH-related fluorescence quenching mechanism of pterin derivatives and the effects of 6-site substituents

Liu

Sun

2018

Can. J. Chem.

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2-Amino-4-hydroxypteridine (pterin) and its derivatives serve as photooxidants and exhibit strong fluorescence. When they interact with hydrogen acceptors such as acetate and phosphate, their fluorescences are significantly quenched in acidic conditions (pH 4.9–5.5) but are retained in basic conditions (pH 10.0–10.5). This pH-related fluorescence quenching mechanism of pterin and its derivatives are fully investigated by using density functional theory (DFT) and time-dependent density functional theory (TD-DFT). Pterin and its derivatives are demonstrated to show favorable excited-state proton transfer (ESPT) abilities in acidic conditions that induce the experimentally observed fluorescence quenching. In contrast, the ESPT processes are found to be retarded due to the lack of strong hydrogen-bonding interactions in basic environments, which sustain their fluorescence. Interestingly, these ESPT processes are found to show different site specificities depending on the 6-site substituents. The introduction of electron-donating substituent activates the N1 site, making it the preferred ESPT site. By contrast, the introduction of an electron-withdrawing substituent activates the N5 site, making it the favorable ESPT site. The substitutions of different functional groups are found to affect the locations of acidic centers during the excitation and relaxation processes. This further affects the hydrogen-bonding patterns and ultimately brings site specificity to the ESPT process.

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Time-Dependent Density Functional Theory Study on a Fluorescent Chemosensor Based on C–H•••F Hydrogen-Bond Interaction

Cited by 44 publications

References 32 publications

Intramolecular charge transfer and sensing mechanism for a colorimetric fluoride sensor based on 1,8-naphthalimide derivatives

Intramolecular charge transfer and sensing mechanism for a colorimetric fluoride sensor based on 1,8-naphthalimide derivatives

Development of a selenide-based fluorescent probe for imaging hypochlorous acid in lysosomes

pH-related fluorescence quenching mechanism of pterin derivatives and the effects of 6-site substituents

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