Intramolecular hydrogen bonding. 4. Dual fluorescence and excited-state proton transfer in 1,5-dihydroxyanthraquinone

1984 ◽  
Vol 88 (14) ◽  
pp. 2954-2960 ◽  
Author(s):  
Mark H. Van Benthem ◽  
G. D. Gillispie
Keyword(s):  
Hydrogen Bonding ◽  
Excited State ◽  
Proton Transfer ◽  
Intramolecular Hydrogen Bonding ◽  
Dual Fluorescence ◽  
Excited State Proton Transfer ◽  
Intramolecular Hydrogen

scholarly journals Investigation of the intramolecular hydrogen bonding interactions and excited state proton transfer mechanism for both Br-BTN and CN-BTN systems

RSC Advances ◽  
2019 ◽  
Vol 9 (40) ◽  
pp. 23004-23011 ◽  
Author(s):  
Dapeng Yang ◽  
Qiaoli Zhang ◽  
Xiaoyan Song ◽  
Tianjie Zhang
Keyword(s):  
Hydrogen Bonding ◽  
Excited State ◽  
Proton Transfer ◽  
Intramolecular Hydrogen Bonding ◽  
Transfer Mechanism ◽  
Hydrogen Bonding Interactions ◽  
Excited State Proton Transfer ◽  
Intramolecular Hydrogen

In the present work, two novel Br-BTN and CN-BTN compounds have been investigated theoretically.

scholarly journals Effect of Water Microsolvation on the Excited-State Proton Transfer of 3-Hydroxyflavone Enclosed in γ-Cyclodextrin

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 843
Author(s):  
Khanittha Kerdpol ◽  
Rathawat Daengngern ◽  
Chanchai Sattayanon ◽  
Supawadee Namuangruk ◽  
Thanyada Rungrotmongkol ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Excited State ◽  
Proton Transfer ◽  
Density Functional ◽  
Photophysical Properties ◽  
Intramolecular Hydrogen Bonding ◽  
Keto Form ◽  
Ring Form ◽  
Hydrophobic Cavity ◽  
Excited State Proton Transfer

The effect of microsolvation on excited-state proton transfer (ESPT) reaction of 3-hydroxyflavone (3HF) and its inclusion complex with γ-cyclodextrin (γ-CD) was studied using computational approaches. From molecular dynamics simulations, two possible inclusion complexes formed by the chromone ring (C-ring, Form I) and the phenyl ring (P-ring, Form II) of 3HF insertion to γ-CD were observed. Form II is likely more stable because of lower fluctuation of 3HF inside the hydrophobic cavity and lower water accessibility to the encapsulated 3HF. Next, the conformation analysis of these models in the ground (S0) and the first excited (S1) states was carried out by density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations, respectively, to reveal the photophysical properties of 3HF influenced by the γ-CD. The results show that the intermolecular hydrogen bonding (interHB) between 3HF and γ-CD, and intramolecular hydrogen bonding (intraHB) within 3HF are strengthened in the S1 state confirmed by the shorter interHB and intraHB distances and the red-shift of O–H vibrational modes involving in the ESPT process. The simulated absorption and emission spectra are in good agreement with the experimental data. Significantly, in the S1 state, the keto form of 3HF is stabilized by γ-CD, explaining the increased quantum yield of keto emission of 3HF when complexing with γ-CD in the experiment. In the other word, ESPT of 3HF is more favorable in the γ-CD hydrophobic cavity than in aqueous solution.

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