Insights into photo-induced excited state intramolecular proton transfer behavior for the novel 2-([1, 1′-biphenyl]-4-yl)-3-hydroxy-4H-chromen-4-one system: Effects of solvent polarity,Journal of Physical Organic Chemistry

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Insights into photo-induced excited state intramolecular proton transfer behavior for the novel 2-([1, 1′-biphenyl]-4-yl)-3-hydroxy-4H-chromen-4-one system: Effects of solvent polarity
Journal of Physical Organic Chemistry ( IF 1.9 ) Pub Date : 2023-04-06 , DOI: 10.1002/poc.4510
Hao Dong ₁ , Xiaoxiao Li ₂ , Shulin Zhao ₃ , Jinfeng Zhao _{2,

3} , Bing Jin ₂

Affiliation

In the light of potential applications for detecting cysteine in vitro and in vivo, 2-([1, 1′-biphenyl]-4-yl)-3-hydroxy-4H-chromen-4-one (B-bph-fla-OH) is explored about its excited state behaviors. Solvent-polarity-related photo-induced hydrogen bond of B-bph-fla-OH indicates nonpolar aprotic solvents largely enhance S₁-state hydrogen bonding interactions. Charge reorganization stemming from photoexcitation and polarity-dependent energy gap between HOMO and LUMO orbitals further reveals the excited state intramolecular proton transfer (ESIPT) tendency. Insights into potential energy curves along ESIPT paths in solvents with different polarities and emission spectral behaviors of proton-transfer tautomer, we present solvent polarity could harness the excited state behaviors for B-bph-fla-OH system.

中文翻译：

深入了解新型 2-([1, 1'-联苯]-4-基)-3-羟基-4H-chromen-4-one 体系的光诱导激发态分子内质子转移行为：溶剂极性的影响

鉴于体外和体内检测半胱氨酸的潜在应用，2-([1, 1'-联苯]-4-基)-3-羟基-4H-chromen-4-one (B-bph-fla- OH）探索了其激发态行为。B-bph-fla-OH 与溶剂极性相关的光诱导氢键表明非极性非质子溶剂很大程度上增强了 S ₁态氢键相互作用。由光激发和 HOMO 和 LUMO 轨道之间极性相关的能隙引起的电荷重组进一步揭示了激发态分子内质子转移（ESIPT）趋势。通过深入了解不同极性溶剂中沿 ESIPT 路径的势能曲线和质子转移互变异构体的发射光谱行为，我们提出溶剂极性可以利用 B-bph-fla-OH 系统的激发态行为。

更新日期：2023-04-06

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