Theoretical insights into the excited-state intramolecular proton transfer (ESIPT) mechanism in a series of amino-type hydrogen-bonding dye molecules bearing the 10-aminobenzo[h]quinoline chromophore

Zhu, Qiuling; Wen, Keke; Feng, Songyan; Wu, Weitai; An, Beibei; Yuan, Huijuan; Guo, Xugeng; Zhang, Jinglai

doi:10.1016/j.dyepig.2017.02.019

Cited by 35 publications

(12 citation statements)

References 39 publications

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“…As with 3-HTC, good agreement between simulated absorption/emission spectra is obtained. Zhu et al 206 studied the excited state intramolecular proton transfer of five molecules containing the 10-aminobenzo[h] quinoline chromophore group.…”

Section: Excited State Intramolecular Proton Transfermentioning

confidence: 99%

A comparison of methods for theoretical photochemistry: Applications, successes and challenges

Hill

Coote

2019

Annual Reports in Computational Chemistry

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Section: Excited State Intramolecular Proton Transfermentioning

confidence: 99%

A comparison of methods for theoretical photochemistry: Applications, successes and challenges

Hill

Coote

2019

Annual Reports in Computational Chemistry

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“…HBs are ubiquitous in molecular structures and have been the research focus due to their distinct properties. Studies have shown that many sensing mechanisms can be well-explained by HB interactions, such as the excited-state intramolecular proton transfer (ESIPT), fluorescence quenching, and intramolecular charge transfer (ICT) (Wen and Jiang, 2004;Plasser et al, 2009;Rawat and Biswas, 2014;Zhu et al, 2017). The ESIPT was first found by Weller when the double fluorescence emission of methyl salicylate was observed (Weller, 1956;Zhou et al, 2014).…”

Section: Introductionmentioning

confidence: 99%

Theoretical Study on the Sensing Mechanism of Novel Hydrazine Sensor TAPHP and Its ESIPT and ICT Processes

Liu

et al. 2020

Front. Chem.

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The photophysical and photochemical properties of the novel hydrazine sensor TAPHP and the TAPDP generated by the cyclization reaction of TAPHP with hydrazine are investigated using the density functional theory and time-dependent density functional theory. The results show that both the excited-state intramolecular proton transfer and intramolecular charge transfer can occur for TAPHP and TAPDP. Analysis of bond parameters and infrared vibrational spectra indicate that hydrogen bonds are enhanced in the first excited state, which is beneficial to excited-state intramolecular proton transfer. The strength of hydrogen bonds is also visualized by using the independent gradient model and topological analysis. The core-valence bifurcation index and bond critical point parameters are further employed to measure hydrogen bonds. The reaction path of proton transfer is obtained through the potential energy curves. The excitation of TAPHP and TAPDP is attributed to the charge transfer excitation, which is determined by the characteristics of the hole-electron distribution. The reaction site and product configuration are verified by atomic charge and 1 H-NMR spectra. The negative free energy difference indicates that the reaction between TAPHP and hydrazine can proceed spontaneously. In addition, the absorption and fluorescence spectra agree well with the experimental results, confirming that TAPHP is an excellent sensor of hydrazine.

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“…This excited keto* form, in theory, possesses significant differences from its corresponding enol species in structure and electronic configuration, resulting in a large Stokes shifted S 1 → S 0 fluorescence. Many novel optoelectronic applications, such as fluorescence sensors, laser dyes and LEDs, UV filters, molecular switches and so forth, are facilitated based on ESIPT reactions. Naturally, the attention focused on this phenomenon is both cognitive and applied, through which it crops up as a demanding subject of research even today.…”

Section: Introductionmentioning

confidence: 99%

The revelation of ESIPT behavior and fluoride response mechanism for (E)‐2‐(((1H‐benzo[d]imidazol‐2‐yl)‐imino)methyl)‐5‐(dimethylamino)‐phenol

Zheng

Zhang

et al. 2019

J of Physical Organic Chem

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Given the tremendous potential of fluorescence sensors in recent years, in this work, as a kind of novel and few studied sensor containing both NH and OH binding sites, (E)-2- (((1H-benzo[d]imidazol-2-yl)-imino)methyl)-5-(dimethylamino)-phenol (bip) has been investigated on the excited state intramolecular proton transfer (ESIPT) based on time-dependent density functional theory (TDDFT) method. Our simulated absorption and fluorescence spectra based on the TDDFT method are in agreement with the experimental results.Two kinds of bip structures could found in the S 1 state, which could be attributed to the ESIPT reaction. Hydrogen bond strengthening has been testified in the S 1 state based on comparing staple bond lengths and bond angles involved in hydrogen bond between S 0 and S 1 states. The calculated infrared (IR) vibrational spectra at the O-H stretching vibrational region and theoretical hydrogen bonding energy also declare the phenomenon of hydrogen bond strengthening. The frontier molecular orbitals (MOs) analysis and Natural bond orbital (NBO) manifest the intramolecular charge transfer (ICT) characteristic for bip chromophore, which reveals the tendency of proton transfer.The potential energy curvess of the S 0 and S 1 states are constructed to explain the mechanism of the proton transfer in excited state in detail. Further, given fluorescence sensing mechanism, we present the addition of fluoride anion can spontaneously capture the hydrogen proton of hydroxyl forming intermolecular hydrogen bond O-H···F, which results in the formation of anion product with response fluoride anion.

show abstract

Theoretical insights into the excited-state intramolecular proton transfer (ESIPT) mechanism in a series of amino-type hydrogen-bonding dye molecules bearing the 10-aminobenzo[h]quinoline chromophore

Cited by 35 publications

References 39 publications

A comparison of methods for theoretical photochemistry: Applications, successes and challenges

A comparison of methods for theoretical photochemistry: Applications, successes and challenges

Theoretical Study on the Sensing Mechanism of Novel Hydrazine Sensor TAPHP and Its ESIPT and ICT Processes

The revelation of ESIPT behavior and fluoride response mechanism for (E)‐2‐(((1H‐benzo[d]imidazol‐2‐yl)‐imino)methyl)‐5‐(dimethylamino)‐phenol

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