Synthesis, spectral analysis, and theoretical investigations of diphenyl fumarate

Journal of Chemical Research-s Pub Date : 2022-03-01 DOI:10.1177/17475198221085550

M. You, Weiqiang Liao, Genlai Zhou, Yihui Bai

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引用次数: 0

Abstract

Diphenyl fumarate is synthesized from maleic anhydride and phenol under solvent-free conditions. The structure of the product is characterized by FTIR, 1H NMR, and 13C NMR. The molecular structure is optimized using the density functional theory approach at the B3LYP/6-311G(d,p) level and the structural parameters are analyzed. Theoretical vibrational frequencies are investigated at the same level; the 1H NMR and 13C NMR are simulated using the default gauge-independent atomic orbital method at the B3LYP/6-31G(d) level and the solvation model density implicit continuum solvation model for chloroform; chemical shifts are scaled using scaling factors available on the cheshirenmr.info website (accessed 12 September 2021). In addition, the UV-Vis absorption and fluorescence emission are simulated using the time-dependent method at the PBE38/6-311G(d,p) level. All the calculated spectral values are compared with the experimental data. A generally good agreement between the experimental and theoretical results is found. The results reveal diphenyl fumarate as a candidate substrate for small-molecule organic fluorophores with a large Stokes shift. This work provides a detailed experimental and theoretical study on the structural and spectral properties of diphenyl fumarate, and thus provides proof for the novel applications of diphenyl fumarate and its derivatives.

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富马酸二苯酯的合成、光谱分析及理论研究

以马来酸酐和苯酚为原料，在无溶剂条件下合成了富马酸二苯酯。通过FTIR、1H NMR和13C NMR对产物的结构进行了表征。利用密度泛函理论方法在B3LYP/6-311G(d,p)水平上对分子结构进行优化，并对结构参数进行分析。在同一水平上研究了理论振动频率;在B3LYP/6-31G(d)水平上，采用默认的与量规无关的原子轨道方法模拟了氯仿的1H NMR和13C NMR，并采用了浓度隐式连续溶剂化模型;化学位移使用cheshirenmr.info网站(2021年9月12日访问)上的比例因子进行缩放。此外，采用时间依赖法模拟了PBE38/6-311G(d,p)水平下的紫外-可见吸收和荧光发射。计算得到的光谱值与实验数据进行了比较。实验结果与理论结果基本一致。结果表明富马酸二苯酯是具有大斯托克斯位移的小分子有机荧光团的候选底物。本研究对富马酸二苯酯的结构和光谱性质进行了详细的实验和理论研究，为富马酸二苯酯及其衍生物的新应用提供了依据。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Chemical Research-s 化学科学, 有机化学, 有机合成

自引率

0.00%

发文量

审稿时长

1 months

期刊介绍： The Journal of Chemical Research is a peer reviewed journal that publishes full-length review and research papers in all branches of experimental chemistry. The journal fills a niche by also publishing short papers, a format which favours particular types of work, e.g. the scope of new reagents or methodology, and the elucidation of the structure of novel compounds. Though welcome, short papers should not result in fragmentation of publication, they should describe a completed piece of work. The Journal is not intended as a vehicle for preliminary publications. The work must meet all the normal criteria for acceptance as regards scientific standards. Papers that contain extensive biological results or material relating to other areas of science may be diverted to more appropriate specialist journals. Areas of coverage include: Organic Chemistry; Inorganic Chemistry; Materials Chemistry; Crystallography; Computational Chemistry.