Theoretical study of heteroatom and substituent effects on excited-state intramolecular proton transfers and electronic properties of amino-type hydrogen bonding molecules

Kanlayakan, Narissa; Kungwan, Nawee

doi:10.1016/j.jlumin.2021.118260

Cited by 16 publications

(6 citation statements)

References 103 publications

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“…An increasing number of researchers have designed and synthesized ESIPT-based fluorescent probes for the selective detection of various anions, metal ions, and small organic molecules [16][17][18][19][20][21]. There are also many theoretical studies for the mechanistic elaboration of various fluorescence probes, as well as the design of novel probes [22][23][24][25][26][27][28][29][30][31][32]. Fluorescent probes for ALP detection generally feature phosphate as a recognition moiety, and after cleavage of the phosphate ester group, a phenolic hydroxyl group will be formed.…”

Section: Introductionmentioning

confidence: 99%

Theoretical Investigation on the ESIPT Process and Detection Mechanism for Dual-Proton Type Fluorescent Probe

Cao

Sun

et al. 2022

IJMS

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Recently, a new fluorescent probeAE-Phoswas reported to detect the activity of alkaline phosphatases (ALP) in different living cell lines. Here, we present an in-depth computational analysis of the mechanism and source of the fluorescence of the AE-Phos probe. There is an intermediate product (AE-OH-Phos) in the experiment as well as a different configuration of products that may emit fluorescence. It is essential to investigate the origin of fluorescence and the detection mechanism of the probe, which could help us eliminate the interference of other substances (including an intermediate product and possible isomers) on fluorescence during the experiment. According to the change of geometric parameters and Infrared spectra, we deduce that the dual intramolecular hydrogen bonds of salicylaldehyde azine (SA) were enhanced at the excited state, while AE-OH-Phos was attenuated. Considering the complex ESIPT behavior of the dual proton-type probe, the potential energy surfaces were further discussed. It can be concluded that the single proton transfer structure of SA (SA-SPT) is the most stable form. Both the concerted double proton transfer process and stepwise single proton transfer process of SA were forbidden. The fluorescence for SA was 438 nm, while that of SA-SPT was 521 nm, which agrees with the experimentally measured fluorescence wavelength (536 nm). The conclusion that single proton transfer occurs in SA is once again verified. In addition, the distribution of electron-hole and relative index was analyzed to investigate the intrinsic mechanism for the fluorescence quenching of the probe and the intermediate product. The identification of the origin of fluorescence sheds light on the design and use of dual-proton type fluorescent probes in the future.

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Section: Introductionmentioning

confidence: 99%

Theoretical Investigation on the ESIPT Process and Detection Mechanism for Dual-Proton Type Fluorescent Probe

Cao

Sun

et al. 2022

IJMS

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“…Interestingly, we noticed that the FPT behavior has become an ultrafast process with no energy barriers in the S L state, which explains why the three molecules do not have a stable enol form in the S L state, and this result is consistent with the analysis of geometric structures. 57 − 59 For the RPT process, the negligible energy barriers (0.367, 0.194, and 0.178 kcal/mol) of HQ, HQS, and HQSe need to be surmounted in the S 0 state, while the energy continues to rise in the S L state, implying that the RPT process prefers to proceed in the S 0 state, which is in agreement with the relative stronger O 1 ···H 1 –N 1 IHB in the S 0 state.…”

Section: Results and Discussionmentioning

confidence: 99%

Theoretical Study on the Atom-Substituted Quinazoline Derivatives with Faint Emission as Potential Sunscreens

Zhang

Shang

et al. 2022

ACS Omega

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Two novel compounds (HQS and HQSe) with excited-state intramolecular proton transfer (ESIPT) properties were designed based on the compound 2-(2-hydroxy-3-ethoxyphenyl)-3 H -quinazolin-4-one (HQ). The parameters related to the ESIPT properties and electronic spectra of HQ and its derivatives were calculated using density functional theory and time-dependent density functional theory methods. The obtained geometric configurations, infrared vibrational spectra, and reduced density gradient scatter plots have shown that the intramolecular hydrogen bond O 1 ···H 1 –N 1 has been weakened upon photoexcitation. Moreover, from the scanned potential energy curves, it can be found that the ESIPT processes of the three compounds have no energy barriers. It is noteworthy that HQS and HQSe can strongly absorb light in the UVA region (∼340 nm) and exhibit weak fluorescence emission in the visible light region, which comes from the keto configuration. The special optical properties of HQS and HQSe can promote their application as potential sunscreen agents.

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Section: Resultsmentioning

confidence: 99%

“…The abundant electron-rich O and N atoms along with the related structures in lignin formed the luminescent clusters and efficiently promoted the PL of lignin, and this electron-donating effect 36 of the heteroatom lone pair electrons enhancing emission is consistent with previous research. [65][66][67] Secondly, a high electron density and nucleophilicity of the amine group and the SB 68 (CvN) in lignin caused charge transfer. 17,69 In essence, the clusters are coupled to the localized excitons by Förster resonant energy transfer (FRET), and subsequently formed an electrostatic network donor-acceptor system.…”

Section: Proposed Mechanism Of Fluorescence Enhancementmentioning

confidence: 99%

Aminated and amidated structures introduced by ethylenediamine pretreatment endow lignin with bright fluorescence

Shi

Wang

et al. 2022

Green Chem.

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Theoretical study of heteroatom and substituent effects on excited-state intramolecular proton transfers and electronic properties of amino-type hydrogen bonding molecules

Cited by 16 publications

References 103 publications

Theoretical Investigation on the ESIPT Process and Detection Mechanism for Dual-Proton Type Fluorescent Probe

Theoretical Investigation on the ESIPT Process and Detection Mechanism for Dual-Proton Type Fluorescent Probe

Theoretical Study on the Atom-Substituted Quinazoline Derivatives with Faint Emission as Potential Sunscreens

Aminated and amidated structures introduced by ethylenediamine pretreatment endow lignin with bright fluorescence

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