The interplay of skeletal deformations and ultrafast excited-state intramolecular proton transfer: Experimental and theoretical investigation of 10-hydroxybenzo[h]quinoline

Schriever, Christian; Barbatti, Mario; Stock, Kai; Aquino, Adélia J. A.; Tunega, Daniel; Lochbrunner, Stefan; Riedle, Eberhard; Vivie‐Riedle, Regina de; Lischka, Hans

doi:10.1016/j.chemphys.2007.10.021

Cited by 95 publications

(162 citation statements)

References 43 publications

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“…Prompt hop of the proton is followed within half of the ν 11 vibrational period. This conclusion is in line with the skeletal deformation model proposed by Schriever et al 9 …”

Section: 31supporting

confidence: 78%

“…[4][5][6][7] Based on those experiments, a multi-dimensional picture for the PES of the ESIPT was proposed. [8][9][10] In this model, vibrational modes involving large amplitude skeletal deformation shorten the distance between the proton and the proton acceptor, and promote the proton transfer. As a result, these vibrational modes are coherently excited on the product state.…”

Section: Introductionmentioning

confidence: 99%

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Ultrafast Excited State Intramolecular Proton Transfer Dynamics of 1-Hydroxyanthraquinone in Solution

Ryu¹,

Kim²,

Kim³

et al. 2013

Bulletin of the Korean Chemical Society

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Proton transfer reaction is one of the most fundamental processes in chemistry and life science. Excited state intramolecular proton transfer (ESIPT) has been studied as a model system of the proton transfer, since it can be conveniently initiated by light. We report ESIPT reaction dynamic of 1-hydroxy-anthraquione (1-HAQ) in solution by highly time-resolved fluorescence. ESIPT time of 1-HAQ is determined to be 45 ± 10 fs directly from decay of the reactant fluorescence and rise of the product fluorescence. High time resolution allows observation of the coherent vibrational wave packet motion in the excited state of the reaction product tautomer. The coherently excited vibrational mode involves large displacement of the atoms, which shortens the distance between the proton donor and the acceptor. With the theoretical analysis, we propose that the ESIPT of 1-HAQ proceeds barrierlessly with assistance of the skeletal vibration, which in turn becomes excited coherently by the ESIPT reaction.

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“…Prompt hop of the proton is followed within half of the ν 11 vibrational period. This conclusion is in line with the skeletal deformation model proposed by Schriever et al 9 …”

Section: 31supporting

confidence: 78%

Section: Introductionmentioning

confidence: 99%

Ultrafast Excited State Intramolecular Proton Transfer Dynamics of 1-Hydroxyanthraquinone in Solution

Ryu¹,

Kim²,

Kim³

et al. 2013

Bulletin of the Korean Chemical Society

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“…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. 10-hydroxybenzo[h]qunoline (HBQ) is such a potent and extensively studied ESIPT molecular system [23][24][25][26]. Since the experimental verification for the occurrence of ESIPT in HBQ [23,24], it has been quite extensively and successfully exploited on the lexicon of applicative research, e.g., probing of biomimicking environments provided by micellar systems having varying surface charges, microheterogeneous environments of supramolecular assemblies of cyclodextrins (CDs) of varying cavity dimensions (a-CD, b-CD, g-CD) [25], as a polarity and pH calibrator [26] and so forth.…”

Section: Introductionmentioning

confidence: 99%

TD–DFT investigation of the potential energy surface for Excited-State Intramolecular Proton Transfer (ESIPT) reaction of 10-hydroxybenzo[h]quinoline: Topological (AIM) and population (NBO) analysis of the intramolecular hydrogen bonding interaction

Paul

Guchhait

2011

Journal of Luminescence

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“…20 Ballistic proton wave packet transfer was proposed as a mechanism for the ESIPT of HBQ based on the isotope dependence and the reaction rate, which is in strong contrast to the conventional model of the skeletal deformation assisted ESIPT. 11 In contrast, ESIPT rate of HBT was determined to be 60 fs, which is much slower than that of HBQ, with no isotope dependence. Together with the wave packet motions in the keto isomer, the results are consistent with the skeletal deformation model for HBT.…”

Section: -19mentioning

confidence: 99%

Photophysical Model of 10-Hydroxybenzo[h]quinoline: Internal Conversion and Excited State Intramolecular Proton Transfer

Lee¹,

Joo²

2014

Bulletin of the Korean Chemical Society

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Photophysics of 10-hydroxybenzo[h]quinoline (HBQ) has been in controversy, in particular, on the nature of the electronic states before and after the excited state intramolecular proton transfer (ESIPT), even though the dynamics and mechanism of the ESIPT have been well established. We report highly time resolved fluorescence spectra over the full emission frequency regions of the enol and keto isomers and the anisotropy in time domain to determine the accurate rates of the population decay, spectral relaxation and anisotropy decay of the keto isomer. We have shown that the ~300 fs component observed frequently in ESIPT dynamics arises from the S 2 → S 1 internal conversion in the reaction product keto isomer and that the ESIPT occurs from the enol isomer in S 1 state to the keto isomer in S 2 state.

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The interplay of skeletal deformations and ultrafast excited-state intramolecular proton transfer: Experimental and theoretical investigation of 10-hydroxybenzo[h]quinoline

Cited by 95 publications

References 43 publications

Ultrafast Excited State Intramolecular Proton Transfer Dynamics of 1-Hydroxyanthraquinone in Solution

Ultrafast Excited State Intramolecular Proton Transfer Dynamics of 1-Hydroxyanthraquinone in Solution

TD–DFT investigation of the potential energy surface for Excited-State Intramolecular Proton Transfer (ESIPT) reaction of 10-hydroxybenzo[h]quinoline: Topological (AIM) and population (NBO) analysis of the intramolecular hydrogen bonding interaction

Photophysical Model of 10-Hydroxybenzo[h]quinoline: Internal Conversion and Excited State Intramolecular Proton Transfer

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