Effect of number and different types of proton donors on excited-state intramolecular single and double proton transfer in bipyridine derivatives: theoretical insights

2020 ◽  
Vol 44 (19) ◽  
pp. 8018-8031
Author(s):  
Komsun Chaihan ◽  
Nawee Kungwan
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Vibrational Mode ◽  
Photophysical Properties ◽  
Reaction Energy ◽  
Topology Analysis ◽  
Double Proton Transfer ◽  
And Topology ◽  
Proton Donors ◽  
Different Types

Intra-HBs are strengthened upon photoexcitation, confirmed by red-shift in vibrational mode and topology analysis. Number and type of donors result in difference in photophysical properties. Occurrence of ESIPT depends on barrier and reaction energy.

Effects of π-expansion, an additional hydroxyl group, and substitution on the excited state single and double proton transfer of 2-hydroxybenzaldehyde and its relative compounds: TD-DFT static and dynamic study

2019 ◽  
Vol 43 (48) ◽  
pp. 19107-19119 ◽  
Author(s):  
Chanatkran Prommin ◽  
Khanittha Kerdpol ◽  
Tinnakorn Saelee ◽  
Nawee Kungwan
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Photophysical Properties ◽  
Dynamic Study ◽  
Hydroxyl Group ◽  
Single Proton ◽  
Double Proton Transfer ◽  
Td Dft ◽  
The Double Proton Transfer

The effects of π-expansion, an extra hydroxyl group, and substituents on the photophysical properties, the excited state single proton transfer and the double proton transfer of 2-hydroxybenzaldehyde and its relatives have been theoretically investigated using TD-DFT.

scholarly journals Theoretical Investigation of Excited-State Intramolecular Double-Proton Transfer Mechanism of Substituent Modified 1, 3-Bis (2-pyridylimino)-4,7-dihydroxyisoindole in Dichloromethane Solution

2021 ◽  
Author(s):  
Xiumin Liu ◽  
Wenzhi Li ◽  
Yuxi Wang ◽  
Yaping Tao ◽  
Yi Wang ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Excited State ◽  
Proton Transfer ◽  
Density Functional ◽  
Photophysical Properties ◽  
Substituent Effects ◽  
Intramolecular Proton Transfer ◽  
Hydrogen Bond Formation ◽  
Dichloromethane Solution ◽  
Double Proton Transfer

Abstract Density functional theory (DFT) and time-dependent DFT (TDDFT) methods were used to investigate substituent effects and excited-state intramolecular double-proton transfer in 1, 3-bis (2-pyridylimino)-4, 7-dihydroxyisoindole (BPI-OH) and its derivatives. The results of a systematic study of the substituent effects of electron-withdrawing groups (F, Cl, and Br) on the adjacent sites of the benzene ring were used to regulate the photophysical properties of the molecules and the dynamics of the proton-transfer process. Geometric structure comparisons and infrared spectroscopic analysis confirmed that strengthening of the intramolecular hydrogen bond in the first excited state (S1) facilitated proton transfer. Functional analysis of the reduction density gradient confirmed these conclusions. Double-proton transfer in BPI-OH is considered to occur in two steps, i.e., BPI-OH (N) →BPI-OH (T1) →BPI-OH (T2), in the ground state (S0) and the S1 state. The potential-energy curves for two-step proton transfer were scanned for both the S0 and S1 states to clarify the mechanisms and pathways of proton transfer. The stepwise path in which two protons are consecutively transferred has a low energy barrier and is more rational and favorable. This study shows that the presence or absence of coordinating groups, and the type of coordinating group, affect the hydrogen-bond strength. A coordinating group enhances hydrogen-bond formation, i.e., it promotes excited-state intramolecular proton transfer.

scholarly journals Theoretical Investigation of Excited-State Intramolecular Double-Proton Transfer Mechanism of Substituent Modified 1, 3-Bis (2-pyridylimino)-4,7-dihydroxyisoindole in Dichloromethane Solution

2021 ◽  
pp. 1-12
Author(s):  
Xiumin Liu ◽  
Heyao Yuan ◽  
Yuxi Wang ◽  
Yaping Tao ◽  
Yi Wang ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Excited State ◽  
Proton Transfer ◽  
Density Functional ◽  
Photophysical Properties ◽  
Substituent Effects ◽  
Intramolecular Proton Transfer ◽  
Hydrogen Bond Formation ◽  
Dichloromethane Solution ◽  
Double Proton Transfer

In this paper, density functional theory (DFT) and time-dependent DFT (TDDFT) methods were used to investigate substituent effects and excited-state intramolecular double-proton transfer (ESIDPT) in 1, 3-bis (2-pyridylimino)-4, 7-dihydroxyisoindole (BPI–OH) and its derivatives. The results of a systematic study of the substituent effects of electron-withdrawing groups (F, Cl and Br) on the adjacent sites of the benzene ring were used to regulate the photophysical properties of the molecules and the dynamics of the proton-transfer process. Geometric structure comparisons and infrared (IR) spectroscopic analysis confirmed that strengthening of the intramolecular hydrogen bond in the first excited state (S1) facilitated proton transfer. Functional analysis of the reduced density gradient confirmed these conclusions. Double-proton transfer in BPI–OH is considered to occur in two steps, i.e., BPI–OH (N) [Formula: see text] BPI–OH (T1) [Formula: see text] BPI–OH (T2), in the ground state (S0) and the S1 state. The potential-energy curves (PECs) for two-step proton transfer were scanned for both the S0 and S1 states to clarify the mechanisms and pathways of proton transfer. The stepwise path in which two protons are consecutively transferred has a low energy barrier and is more rational and favorable. This study shows that the presence or absence of coordinating groups, and the type of coordinating group, affect the hydrogen-bond strength. A coordinating group enhances hydrogen-bond formation, i.e., it promotes excited-state intramolecular proton transfer (ESIPT).

Heavy mass effect on excited-state double-proton transfer in the 7-azaindole dimer by Cl substitution

2007 ◽  
Vol 441 (4-6) ◽  
pp. 176-180 ◽  
Author(s):  
Xuan Zhang ◽  
Yusuke Komoto ◽  
Kenji Sakota ◽  
Masayuki Nakagaki ◽  
Haruyuki Nakano ◽  
...  
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Mass Effect ◽  
Double Proton Transfer

Ground and Excited-State Acetic Acid Catalyzed Double Proton Transfer in 2-Aminopyridine†

2003 ◽  
Vol 107 (18) ◽  
pp. 3244-3253 ◽  
Author(s):  
Fa-Tsai Hung ◽  
Wei-Ping Hu ◽  
Tsung-Hui Li ◽  
Chung-Chih Cheng ◽  
Pi-Tai Chou
Keyword(s):  
Acetic Acid ◽  
Excited State ◽  
Proton Transfer ◽  
Double Proton Transfer ◽  
Acid Catalyzed
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