Revealing and comparing different excited‐state intramolecular proton transfer processes for 3‐(4‐dimethylamino‐phenyl)‐1‐(4‐fluoro‐2‐hydroxy‐phenyl)‐propenone and 3‐(4‐dimethylamino‐phenyl)‐1‐(4‐fluoro‐2‐hydroxy‐phenyl)‐3‐hydroxy‐propenon,Journal of the Chinese Chemical Society

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Revealing and comparing different excited‐state intramolecular proton transfer processes for 3‐(4‐dimethylamino‐phenyl)‐1‐(4‐fluoro‐2‐hydroxy‐phenyl)‐propenone and 3‐(4‐dimethylamino‐phenyl)‐1‐(4‐fluoro‐2‐hydroxy‐phenyl)‐3‐hydroxy‐propenon
Journal of the Chinese Chemical Society ( IF 1.6 ) Pub Date : 2020-03-31 , DOI: 10.1002/jccs.201900480
Haiyan Gao ₁ , Xiaoyan Song ₁ , Xiaohui Yang ₁ , Dapeng Yang _{1,

2}

Affiliation

Two novel 2′‐hydroxychalcone derivatives (i.e., M1 and M2) are explored in this work. We mainly focus on investigating the effects of photoexcitation on hydrogen bonds and on the excited‐state intramolecular proton transfer (ESIPT) process. On the basis of calculations of electrostatic potential surface and intramolecular interactions, we verify the formation of hydrogen bond O1H2···O3 in both S₀ and S₁ states. Exploring the ultraviolet–visible spectra in the liquid phase, our simulated results reappear in the experimental phenomenon. Analyzing molecular geometry and infrared stretching vibrational spectra, we confirm O1H2···O3 is strengthened for both M1 and M2 in the S₁ state. We further confirm that charge redistribution facilitates ESIPT tendency. Constructing potential energy curves, we find the ultrafast ESIPT behavior for M1, which is because of the deficiency of side hydroxyl moiety comparing with M2. This work makes a reasonable affiliation of the ESIPT mechanism for M1 and M2. We wish this paper could facilitate understanding these two novel systems and promote their applications.

中文翻译：

揭示和比较3-（4-二甲基氨基-苯基）-1-（4-氟-2-羟基-苯基）丙酮和3-（4-二甲基氨基-苯基）-1-酮的不同激发态分子内质子转移过程（4-氟-2-羟基苯基）-3-羟基丙烷

在这项工作中探索了两个新颖的2'-羟基查耳酮衍生物（即M1和M2）。我们主要致力于研究光激发对氢键的影响以及激发态分子内质子转移（ESIPT）过程。在计算静电势表面和分子内相互作用的基础上，我们验证了在S ₀和S ₁状态下氢键O1H2 ···O3的形成。探索液相中的紫外可见光谱，我们的模拟结果再次出现在实验现象中。分析分子几何结构和红外拉伸振动光谱，我们可以确定S ₁中的M1和M2都增强了O1H2 ···O3州。我们进一步证实，电荷的重新分配促进了ESIPT趋势。绘制势能曲线，我们发现M1具有超快的ESIPT行为，这是因为与M2相比，侧羟基部分不足。这项工作使M1和M2的ESIPT机制成为合理的成员。我们希望本文能促进对这两个新颖系统的理解并促进它们的应用。

更新日期：2020-03-31

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