Reconsideration of the excited-state double proton transfer (ESDPT) in 2-aminopyridine/acid systems: role of the intermolecular hydrogen bonding in excited states

2009 ◽  
Vol 11 (21) ◽  
pp. 4385 ◽  
Author(s):  
Shuo Chai ◽  
Guang-Jiu Zhao ◽  
Peng Song ◽  
Song-Qiu Yang ◽  
Jian-Yong Liu ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Excited State ◽  
Proton Transfer ◽  
Excited States ◽  
Intermolecular Hydrogen Bonding ◽  
Double Proton Transfer

scholarly journals Role of intramolecular hydrogen bonding in the excited-state intramolecular double proton transfer (ESIDPT) of calix[4]arene: A TDDFT study

Open Physics ◽  
2016 ◽  
Vol 14 (1) ◽  
pp. 602-609 ◽  
Author(s):  
Se Wang ◽  
Zhuang Wang ◽  
Ce Hao
Keyword(s):  
Hydrogen Bonding ◽  
Excited State ◽  
Hydrogen Bonds ◽  
Proton Transfer ◽  
Ground State ◽  
Intramolecular Hydrogen Bonding ◽  
Intramolecular Hydrogen Bonds ◽  
Double Proton Transfer ◽  
Intramolecular Hydrogen

AbstractThe time-dependent density functional theory (TDDFT) method was performed to investigate the excited-state intramolecular double proton transfer (ESIDPT) reaction of calix[4]arene (C4A) and the role of the intramolecular hydrogen bonds in the ESIDPT process. The geometries of C4A in the ground state and excited states (S1, S2 and T1) were optimized. Four intramolecular hydrogen bonds formed in the C4A are strengthened or weakened in the S2 and T1 states compared to those in the ground state. Interestingly, upon excitation to the S1 state of C4A, two protons H1 and H2 transfer along the two intramolecular hydrogen bonds O1-H1···O2 and O2-H2···O3, while the other two protons do not transfer. The ESIDPT reaction breaks the primary symmetry of C4A in the ground state. The potential energy curves of proton transfer demonstrate that the ESIDPT process follows the stepwise mechanism but not the concerted mechanism. Findings indicate that intramolecular hydrogen bonding is critical to the ESIDPT reactions in intramolecular hydrogen-bonded systems.

Photophysics, Excited-state Double-Proton Transfer and Hydrogen-bonding Properties of 5-Deazaalloxazines

2014 ◽  
pp. n/a-n/a ◽  
Author(s):  
Dorota Prukala ◽  
Igor Khmelinskii ◽  
Jacek Koput ◽  
Mateusz Gierszewski ◽  
Tomasz Pędziński ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Excited State ◽  
Proton Transfer ◽  
Double Proton Transfer ◽  
Bonding Properties

Effects of intermolecular hydrogen bonding on the excited-state proton transfer properties of the cinnamonitrile–methanol complex

2013 ◽  
Vol 91 (3) ◽  
pp. 229-234 ◽  
Author(s):  
Dapeng Yang ◽  
Ruiquan Qi
Keyword(s):  
Hydrogen Bonding ◽  
Excited State ◽  
Charge Transfer ◽  
Proton Transfer ◽  
Density Functional ◽  
Dft Method ◽  
Electronic Energy ◽  
Intermolecular Hydrogen Bonding ◽  
Excited State Proton Transfer ◽  
Hydrogen Bonded

The time-dependent density functional theory (TD-DFT) method was used to study the excited-state proton transfer (ESPT) properties of the hydrogen-bonded cinnamonitrile (3TPAN)–methanol (MeOH) complex (3TPAN–MeOH). The intermolecular hydrogen bonds N1···H11 in both the ground state S0 and the excited state S1 were demonstrated by the optimized geometric structures of the hydrogen-bonded 3TPAN–MeOH complex. While in the excited state S3, a new hydrogen bond H11···O1 was formed after the ESPT took place from the hydrogen-bonded MeOH molecule to the 3TPAN moiety. It was demonstrated that the electronic transitions of the S1 states for both the 3TPAN monomer (including the S3 state) and the hydrogen-bonded 3TPAN–MeOH complex should be of a localized-excited (LE) nature on the 3TPAN molecule, while the S3 state of the hydrogen-bonded 3TPAN–MeOH complex should be of charge transfer (CT) character from the hydrogen-bonded MeOH molecule (through O1···H11) to the 3TPAN moiety. The S3-state proton transfer and charge transfer due to the intermolecular hydrogen-bonding interaction should be the reasons for the remarkable redshift (0.91 eV) of the S3-state electronic energy for the hydrogen-bonded 3TPAN–MeOH complex compared with that of the 3TPAN monomer.

Excited-State Double Proton Transfer in 3-Formyl-7-azaindole:  Role of thenπ*State in Proton-Transfer Dynamics

2000 ◽  
Vol 104 (39) ◽  
pp. 8863-8871 ◽  
Author(s):  
Pi-Tai Chou ◽  
Guo-Ray Wu ◽  
Ching-Yen Wei ◽  
Mei-Ying Shiao ◽  
Yun-I Liu
Keyword(s):  
Excited State ◽  
Proton Transfer ◽  
Double Proton Transfer
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