Insights into Hydrogen Bonding Effect as Well as Excited State Intramolecular Proton Transfer Associated with Solvent Polarity and Atomic Electronegativity for 2-Phenyl-3-Hydroxybenzo[g]quinolone

被引:3
作者
Zhao, Jinfeng [1 ,3 ]
Fan, Liming [1 ]
Li, Liu [1 ]
Jin, Bing [3 ]
Tang, Zhe [2 ,3 ]
机构
[1] Shenyang Normal Univ, Coll Phys Sci & Technol, Shenyang 110034, Peoples R China
[2] Tianjin Univ Technol, Life & Hlth Intelligent Res Inst, Tianjin Key Lab Drug Targeting & Bioimaging, Tianjin 300384, Peoples R China
[3] Shandong Univ, Inst Mol Sci & Engn, Inst Frontier & Interdisciplinary Sci, Qingdao 266237, Peoples R China
来源
CHEMISTRYSELECT | 2023年 / 8卷 / 22期
关键词
Excited-state intramolecular proton transfer; Intramolecular hydrogen bond; Solvent polarity; Atomic electronegativity; Charge redistribution; CHARGE-TRANSFER; MECHANISM; SINGLE; CONTINUUM; PROBE;
D O I
10.1002/slct.202300933
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Inspired by the excellent photochemical properties of 3-hydroxyflavone and its derivatives, in this work, the novel 2-phenyl-3-hydroxybenzo[g]quinolone (2P3HBQ) fluorophore is explored about its photo-induced behaviors. By investigating the photoexcitation characteristics in different solvents as well as the substituted atomic electronegativity (O -> S -> Se), the solvent-polarity-related and atomic-electronegativity-dependent photo-induced hydrogen bond of 2P3HBQ and its derivatives (2P3HBQ-O, 2P3HBQ-S and 2P3HBQ-Se) indicates the S-1-state hydrogen bonding interactions could be enhanced. Particularly, the nonpolar solvent environment and low atomic electronegativity substitution play large roles in strengthening hydrogen bonding effects. Charge reorganization stemming from photoexcitation, strengthening excited state hydrogen bond effects, and the intramolecular charge transfer (ICT) via frontier molecular orbitals (MOs) further reveals the excited state intramolecular proton transfer (ESIPT) tendency. Via the manner of constructing potential energy curves (PECs) with restricted optimization, we elaborate and reveal the novel solvent-polarity-regulated and the atomic-electronegativity-controlled ESIPT dynamical behaviors.
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页数:8
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