Exploring the Excited State Behavior for 2-(phenyl)imidazo[4,5-c]pyridine in Methanol Solvent

Overview

Journal Sci Rep

Specialty Science

Date 2017 Sep 17

PMID 28916799

Citations 2

Authors

Dapeng Yang

Min Jia

Jingyuan Wu

Xiaoyan Song

Affiliations

Soon will be listed here.

Abstract

In this present work, we theoretically investigate the excited state mechanism for the 2-(phenyl)imidazo[4,5-c]pyridine (PIP-C) molecule combined with methanol (MeOH) solvent molecules. Three MeOH molecules should be connected with PIP-C forming stable PIP-C-MeOH complex in the S state. Upon the photo-excitation, the hydrogen bonded wires are strengthened in the S state. Particularly the deprotonation process of PIP-C facilitates the excited state intermolecular proton transfer (ESIPT) process. In our work, we do verify that the ESIPT reaction should occur due to the low potential energy barrier 8.785 kcal/mol in the S state. While the intersection of potential energy curves of S and S states result in the nonradiation transition from S to S state, which successfully explain why the emission peak of the proton-transfer PIP-C-MeOH-PT form could not be reported in previous experiment. As a whole, this work not only put forward a new excited state mechanism for PIP-C system, but also compensates for the defects about mechanism in previous experiment.

Citing Articles

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References

Zhang Z, Hsu Y, Chen Y, Chen C, Lin T, Shen J . New six- and seven-membered ring pyrrole-pyridine hydrogen bond systems undergoing excited-state intramolecular proton transfer. Chem Commun (Camb). 2014; 50(95):15026-9. DOI: 10.1039/c4cc07109c. View

Li H, Yin H, Liu X, Shi Y, Jin M, Ding D . An experimental and theoretical study of solvent hydrogen-bond-donating capacity effects on ultrafast intramolecular charge transfer of LD 490. Spectrochim Acta A Mol Biomol Spectrosc. 2017; 184:270-276. DOI: 10.1016/j.saa.2017.05.027. View

Hobza P, Havlas Z . Blue-Shifting Hydrogen Bonds. Chem Rev. 2001; 100(11):4253-4264. DOI: 10.1021/cr990050q. View

Tuckerman M, Marx D, Parrinello M . The nature and transport mechanism of hydrated hydroxide ions in aqueous solution. Nature. 2002; 417(6892):925-9. DOI: 10.1038/nature00797. View

Li G, Zhao G, Liu Y, Han K, He G . TD-DFT study on the sensing mechanism of a fluorescent chemosensor for fluoride: excited-state proton transfer. J Comput Chem. 2010; 31(8):1759-65. DOI: 10.1002/jcc.21466. View

Chung M, Liao J, Tang K, Hsieh C, Lin T, Liu C . Structural tuning intra- versus inter-molecular proton transfer reaction in the excited state. Phys Chem Chem Phys. 2012; 14(25):9006-15. DOI: 10.1039/c2cp23938h. View

Yu F, Li P, Li G, Zhao G, Chu T, Han K . A near-IR reversible fluorescent probe modulated by selenium for monitoring peroxynitrite and imaging in living cells. J Am Chem Soc. 2011; 133(29):11030-3. DOI: 10.1021/ja202582x. View

Miao C, Shi Y . Reconsideration on hydrogen bond strengthening or cleavage of photoexcited coumarin 102 in aqueous solvent: a DFT/TDDFT study. J Comput Chem. 2011; 32(14):3058-61. DOI: 10.1002/jcc.21888. View

Tseng H, Lin T, Chen C, Lin T, Chen Y, Liu J . A new class of N-H proton transfer molecules: wide tautomer emission tuning from 590 nm to 770 nm via a facile, single site amino derivatization in 10-aminobenzo[h]quinoline. Chem Commun (Camb). 2015; 51(89):16099-102. DOI: 10.1039/c5cc06633f. View

10.

Zhao Y, Truhlar D . Comparative DFT study of van der Waals complexes: rare-gas dimers, alkaline-earth dimers, zinc dimer, and zinc-rare-gas dimers. J Phys Chem A. 2006; 110(15):5121-9. DOI: 10.1021/jp060231d. View

11.

Herbert J, Zhang X, Morrison A, Liu J . Beyond Time-Dependent Density Functional Theory Using Only Single Excitations: Methods for Computational Studies of Excited States in Complex Systems. Acc Chem Res. 2016; 49(5):931-41. DOI: 10.1021/acs.accounts.6b00047. View

12.

Xia L, Wang J, Ma C, Wu S, Song P . Charge Distribution Dependent Spectral Analysis of the Oxidized Diferrocenyl-Oligothienylene-Vinylene Molecular Wires. Sci Rep. 2016; 6:35726. PMC: 5069631. DOI: 10.1038/srep35726. View

13.

Song P, Ding J, Chu T . TD-DFT study on the excited-state proton transfer in the fluoride sensing of a turn-off type fluorescent chemosensor based on anthracene derivatives. Spectrochim Acta A Mol Biomol Spectrosc. 2012; 97:746-52. DOI: 10.1016/j.saa.2012.07.010. View

14.

Li G, Zhao G, Han K, He G . A TD-DFT study on the cyanide-chemosensing mechanism of 8-formyl-7-hydroxycoumarin. J Comput Chem. 2010; 32(4):668-74. DOI: 10.1002/jcc.21651. View

15.

Peng C, Shen J, Chen Y, Wu P, Hung W, Hu W . Optically Triggered Stepwise Double-Proton Transfer in an Intramolecular Proton Relay: A Case Study of 1,8-Dihydroxy-2-naphthaldehyde. J Am Chem Soc. 2015; 137(45):14349-57. DOI: 10.1021/jacs.5b08562. View

16.

Lin T, Tang K, Yang S, Shen J, Cheng Y, Pan H . The empirical correlation between hydrogen bonding strength and excited-state intramolecular proton transfer in 2-pyridyl pyrazoles. J Phys Chem A. 2012; 116(18):4438-44. DOI: 10.1021/jp300340t. View

17.

Liu Y, Lan S, Zhu C, Lin S . Intersystem Crossing Pathway in Quinoline-Pyrazole Isomerism: A Time-Dependent Density Functional Theory Study on Excited-State Intramolecular Proton Transfer. J Phys Chem A. 2015; 119(24):6269-74. DOI: 10.1021/acs.jpca.5b03557. View

18.

Zhao J, Chen J, Cui Y, Wang J, Xia L, Dai Y . A questionable excited-state double-proton transfer mechanism for 3-hydroxyisoquinoline. Phys Chem Chem Phys. 2014; 17(2):1142-50. DOI: 10.1039/c4cp04135f. View

19.

Liu L, Yang D, Li P . pH-related and site-specific excited-state proton transfer from pterin to acetate. J Phys Chem B. 2014; 118(40):11707-14. DOI: 10.1021/jp5082017. View

20.

Chen Y, Tang K, Chen Y, Shen J, Wu Y, Liu S . Insight into the mechanism and outcoupling enhancement of excimer-associated white light generation. Chem Sci. 2018; 7(6):3556-3563. PMC: 6007176. DOI: 10.1039/c5sc04902d. View