Dynamics of Ground‐ and Excited‐State Intramolecular Proton Transfer Reactions

Zwan, Gert van der

doi:10.1002/9783527658824.ch9

Cited by 2 publications

(2 citation statements)

References 34 publications

(46 reference statements)

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“…Excited-State Proton Transfer (ESPT) is an important reaction that controls the functioning of various biological systems [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 ]. Probe molecules in various biological systems, based on this mechanism, have also been suggested recently [ 10 , 11 ].…”

Section: Introductionmentioning

confidence: 99%

Excited-State Intramolecular Proton Transfer: A Short Introductory Review

2021

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In this short review, we attempt to unfold various aspects of excited-state intramolecular proton transfer (ESIPT) from the studies that are available up to date. Since Weller’s discovery of ESIPT in salicylic acid (SA) and its derivative methyl salicylate (MS), numerous studies have emerged on the topic and it has become an attractive field of research because of its manifold applications. Here, we discuss some critical aspects of ESIPT and tautomerization from the mechanistic viewpoint. We address excitation wavelength dependence, anti-Kasha ESIPT, fast and slow ESIPT, reversibility and irreversibility of ESIPT, hydrogen bonding and geometrical factors, excited-state double proton transfer (ESDPT), concerted and stepwise ESDPT.

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Section: Introductionmentioning

confidence: 99%

Excited-State Intramolecular Proton Transfer: A Short Introductory Review

2021

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“…Absorption of a photon can initiate numerous intramolecular processes. Among these, the excited-state intramolecular proton transfer (ESIPT) reaction plays a prominent role. − ESIPT occurs in molecules that have proton-donating and proton-accepting centers electronically conjugated through the molecular skeleton and which, additionally, show significant changes in their electron density distribution after excitation. , …”

Section: Introductionmentioning

confidence: 99%

Solving the Puzzle of Unusual Excited-State Proton Transfer in 2,5-Bis(6-methyl-2-benzoxazolyl)phenol

et al. 2022

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2,5-Bis(6-methyl-2-benzoxazolyl)phenol ( BMP ) exhibits an ultrafast excited-state intramolecular proton transfer (ESIPT) when isolated in supersonic jets, whereas in condensed phases the phototautomerization is orders of magnitude slower. This unusual situation leads to nontypical photophysical characteristics: dual fluorescence is observed for BMP in solution, whereas only a single emission, originating from the phototautomer, is detected for the ultracold isolated molecules. In order to understand the completely different behavior in the two regimes, detailed photophysical studies have been carried out. Kinetic and thermodynamic parameters of ESIPT were determined from stationary and transient picosecond absorption and emission for BMP in different solvents in a broad temperature range. These studies were combined with time-dependent- density functional theory quantum-chemical modeling. The excited-state double-well potential for BMP and its methyl-free analogue were calculated by applying different hybrid functionals and compared with the results obtained for another proton-transferring molecule, 2,5-bis(5-ethyl-2-benzoxazolyl)hydroquinone ( DE-BBHQ ). The results lead to the model that explains the difference in proton-transfer properties of BMP in vacuum and in the condensed phase by inversion of the two lowest singlet states occurring along the PT coordinate.

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Dynamics of Ground‐ and Excited‐State Intramolecular Proton Transfer Reactions

Cited by 2 publications

References 34 publications

Excited-State Intramolecular Proton Transfer: A Short Introductory Review

Excited-State Intramolecular Proton Transfer: A Short Introductory Review

Solving the Puzzle of Unusual Excited-State Proton Transfer in 2,5-Bis(6-methyl-2-benzoxazolyl)phenol

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