Insights into the excited state hydrogen bond and proton transfer behaviors associated with solvent polarity for NHBQ fluorophore: a theoretical study

被引：7

作者：

Dong, Hao ^{[2
]}

Jin, Bing ^{[3
]}

Fan, Liming ^{[1
]}

Zhao, Jinfeng ^{[1
,3
]}

Li, Xiaoxiao ^{[3
]}

机构：

[1] Shenyang Normal Univ, Coll Phys Sci & Technol, Shenyang 110034, Peoples R China

[2] North China Elect Power Univ, Hebei Key Lab Phys & Energy Technol Dept Math & Ph, Baoding 071003, Peoples R China

[3] Shandong Univ, Inst Mol Sci & Engn, Inst Frontier & Interdisciplinary Sci, Qingdao 266237, Peoples R China

来源：

THEORETICAL CHEMISTRY ACCOUNTS | 2023年 / 142卷 / 04期

关键词：

Excited-state intramolecular proton transfer; Intramolecular hydrogen bond; Solvent polarity; Charge redistribution; Potential energy curve; PHOTOPHYSICAL PROPERTIES; NONCOVALENT INTERACTIONS; ESIPT MECHANISM; CHEMISTRY; THERMOCHEMISTRY; SPECTROSCOPY; CONTINUUM; SURFACE; SOLUTE;

D O I：

10.1007/s00214-023-02979-w

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Inspired by the excellent photochemical properties of hydroxybenzo[h]quinoline and its derivatives, in this work, the novel electron withdrawing nitro substituted HBQ (i.e., NHBQ) fluorophore is explored about its photo-induced behaviors. By investigating the photoexcitation characteristics in different solvents, the solvent-polarity-related photo-induced hydrogen bond of NHBQ indicates polar aprotic solvents largely enhance S-1-state hydrogen bond interactions. Charge reorganization stemming from photoexcitation, strengthening excited state hydrogen bond effects, and the polarity-dependent energy gap of frontier molecular orbitals further reveals the excited state intramolecular proton transfer (ESIPT) tendency. Insights into potential energy curves along ESIPT paths in solvents with different polarities, we present that solvent polarity could harness the ESIPT behavior for NHBQ compound.

引用

页数：8

共 59 条

[51] Excited State Electronic Structures and Photochemistry of Heterocyclic Annulated Perylene (HAP) Materials Tuned by Heteroatoms: S, Se, N, O, C, Si, and B [J].

Zhao, Guang-Jiu ;

Han, Ke-Li .

JOURNAL OF PHYSICAL CHEMISTRY A, 2009, 113 (16) :4788-4794

[52]

Zhao J., 2022, CHEMISTRYSELECT, V7

[53] Unraveling photo-induced proton transfer mechanism and proposing solvent regulation manner for the two intramolecular proton-transfer-site BH-BA fluorophore [J].

Zhao, Jinfeng ;

Jin, Bing ;

Tang, Zhe .

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2023, 288

[54] Solvent-polarity-dependent conformation and ESIPT behaviors for 2-(benzimidazol-2-yl)-3-hydroxychromone: a novel dynamical mechanism [J].

Zhao, Jinfeng ;

Jin, Bing ;

Tang, Zhe .

PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2022, 24 (45) :27660-27669

[55] The investigation of ESPT for 2,8-diphenyl-3,7-dihydroxy-4H, 6H-pyrano[3,2-g]-chromene-4,6-dione: single or double? [J].

Zhao, Jinfeng ;

Li, Peng .

RSC ADVANCES, 2015, 5 (90) :73619-73625

[56] New Excited-State Proton Transfer Mechanisms for 1,8Dihydroxydibenzo[a,h]phenazine [J].

Zhao, Jinfeng ;

Yao, Hongbin ;

Liu, Jianyong ;

Hoffmann, Mark R. .

JOURNAL OF PHYSICAL CHEMISTRY A, 2015, 119 (04) :681-688

[57] The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals [J].

Zhao, Yan ;

Truhlar, Donald G. .

THEORETICAL CHEMISTRY ACCOUNTS, 2008, 120 (1-3) :215-241

[58] Unraveling the Detailed Mechanism of Excited-State Proton Transfer [J].

Zhou, Panwang ;

Han, Keli .

ACCOUNTS OF CHEMICAL RESEARCH, 2018, 51 (07) :1681-1690

[59] Unveiling the sensing mechanism and luminescence property of a new ESIPT-based fluorescent sensor for detecting Zn2+ [J].

Zhuang, Hongbin ;

Shi, Wei ;

Zhao, Guijie ;

Yang, Yunfan ;

Li, Yongqing .

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2022, 282

← 1 2 3 4 5 6 →