Synthesis, Spectral Properties and Theoretical Studies of 1,4-Bis[2-(4-pyridyl)ethenyl]benzene Derivatives

doi:10.6023/cjoc201606040

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (2): 394-402.DOI: 10.6023/cjoc201606040 Previous Articles Next Articles

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1,4-双[2-(4-吡啶基)乙烯基]苯衍生物的合成、光谱性质及理论研究

欧亚平^a, 张静^b, 庾江喜^a, 朱小明^a

a 衡阳师范学院化学与材料科学学院功能金属有机材料湖南省普通高等学校重点建设实验室衡阳 421008;
b 华中师范大学化学学院农药与化学生物学教育部重点实验室武汉 430079

收稿日期:2016-06-29 修回日期:2016-09-02 发布日期:2016-10-18
通讯作者: 欧亚平 E-mail:ouyaping@hynu.edu.cn
基金资助:
湖南省高校重点实验室开放基金（No.GN15K05）及衡阳师范学院科研启动基金（No.14B23）资助项目.

Synthesis, Spectral Properties and Theoretical Studies of 1,4-Bis[2-(4-pyridyl)ethenyl]benzene Derivatives

Ou Yaping^a, Zhang Jing^b, Yu Jiangxi^a, Zhu Xiaoming^a

a Key Laboratory of Functional Organometallic Materials of Hunan Province College, College of Chemistry and Material Science, Hengyang Normal University;Hengyang 421008;
b Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, Central China Normal University, Wuhan 430079

Received:2016-06-29 Revised:2016-09-02 Published:2016-10-18
Supported by:
Project supported by the Opening Subjects of Key Laboratory of Functional Organometallic Materials of Hunan Province (No. GN15K05), and the Scientific Research Foundation of the Hengyang Normal University (No. 14B23).

1. Synthesis, Spectral Properties and Theoretical Studies of 1,4-Bis[2-(4-pyridyl)ethenyl]benzene Derivatives.PDF(889KB)

Abstract

Four asymmetric hydrogen-bond acceptors of 1,4-bis[2-(4-pyridyl)ethenyl]benzene derivatives with higher yields were synthesized through the classical Witting-Horner and Sonogashira cross-coupling reactions, and their structures and spectral properties were investigated. The series of compounds all have been characterized by NMR, MS and element analysis. Crystal structures indicated that the conformation of hydrogen-bond self-assemble may be change due to the hindrance effect from the arylacetyl group in o-position of benzene. UV-Vis spectra combined with time-dependent density functional theory (TDDFT) calculation results showed that target compounds all display a strong π→π^* and ICT transition absorptions. Fluorescence spectrum indicated that gradual increasing of conjugate systems make their emission peak tend to a red shift, which is conducive to π-π accumulation. Above results will provide certain synthetic basis and theoretical foundation for subsequent studies about regioselectivity of hydrogen-bond self-assemble and cyclization reactions from light.

Key words: Asymmetric hydrogen-bond acceptor, 1,4-Bis[2-(4-pyridyl)ethenyl]benzene, Crystal structure, Spectral properties

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Ou Yaping, Zhang Jing, Yu Jiangxi, Zhu Xiaoming. Synthesis, Spectral Properties and Theoretical Studies of 1,4-Bis[2-(4-pyridyl)ethenyl]benzene Derivatives[J]. Chin. J. Org. Chem., 2017, 37(2): 394-402.

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1,4-双[2-(4-吡啶基)乙烯基]苯衍生物的合成、光谱性质及理论研究

Synthesis, Spectral Properties and Theoretical Studies of 1,4-Bis[2-(4-pyridyl)ethenyl]benzene Derivatives

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