2015
DOI: 10.1007/s10876-015-0893-7
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Excited-State Intramolecular Proton Transfer Reaction of 3-Hydroxyflavone

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Cited by 17 publications
(8 citation statements)
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“…All orbitals except HOMO-3 have the π characteristic; only HOMO-3 has an in-plane lone pair contribution from the carbonyl oxygen. In the bright S 1 (HOMO–LUMO) excitation, electron density is transferred from the OH-1 group in HOMO to the O atom in LUMO, making the proton more acidic and the O atom (the proton acceptor) more basic. ,, By this electron rearrangement, the ESIPT is facilitated. The S 2 state is characterized as having the n π* characteristic.…”
Section: Results and Discussionmentioning
confidence: 99%
“…All orbitals except HOMO-3 have the π characteristic; only HOMO-3 has an in-plane lone pair contribution from the carbonyl oxygen. In the bright S 1 (HOMO–LUMO) excitation, electron density is transferred from the OH-1 group in HOMO to the O atom in LUMO, making the proton more acidic and the O atom (the proton acceptor) more basic. ,, By this electron rearrangement, the ESIPT is facilitated. The S 2 state is characterized as having the n π* characteristic.…”
Section: Results and Discussionmentioning
confidence: 99%
“…From the method of choice, among seven tested functionals, the most suitable method for reproducing the enol absorption spectra of all molecules is the B3LYP because this method provides the most satisfactory agreement with the experimental data. Moreover, previous studies have been proven that the B3LYP and TD-B3LYP functionals with TZVP basis set are suitable to describe electronic and photophysical properties as well as the PT process of ESIPT molecules [29,[57][58][59][60][61][62]. Therefore, the B3LYP was further em ployed to optimize the enol form in the S 1 state and the keto form both in S 0 and the S 1 states of all molecules.…”
Section: Static Calculationsmentioning
confidence: 99%
“…3-Hydroxyflavone (3HF), one of the flavonol family as shown in Fig. 1 (when X = O), has been not only used as fluorescent probes but also as a model molecule to study the ESIPT process due to its unique large Stokes shift (190 nm) [25] and dual emissions [26][27][28][29]. However, a wider application of 3HF as a fluorescent probe has been limited due to its enol absorption and keto emission not being in the longer wavelength, the proper ratio of dual emission (N * /I * ) and low intensity of fluorescence.…”
Section: Introductionmentioning
confidence: 99%
“…[3][4][5][6] One of the most intriguing phenomena in the photochemistry of hydroxychromones (HCs) and their derivatives is the ultrafast (subpicosecond timescale, cf., Table 1) excited-state intramolecular proton transfer (ESIPT) reaction. [11][12][13][14][15][16][17][18] Upon photoexcitation to the low-lying singlet excited states, these molecules would exhibit the proton transfer process where the proton of hydroxyl group is transferred to the carbonyl group without affecting the structural rigidity of benzopyran (see Figure 1). Experimentally observed faster rate of keto tautomer product formation was accounted for the "promoting effect" of a lowfrequency O─H in-plane bending vibration.…”
Section: Introductionmentioning
confidence: 99%