Design, Synthesis and Anion Recognition of Benzocoumarin-Based Thiourea Receptors

doi:10.6023/cjoc201505038

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (10): 2184-2190.DOI: 10.6023/cjoc201505038 Previous Articles Next Articles

Notes

苯并香豆素硫脲类受体分子的设计、合成与阴离子识别研究

晏希泉^a, 卓继斌^a, 王吉成^a, 谢莉莉^a,b, 袁耀锋^a,b

a 福州大学化学学院福州 350116;
b 中国科学院福建物质结构研究所结构化学国家重点实验室福州 350002

收稿日期:2015-05-26 修回日期:2015-06-12 发布日期:2015-06-19
通讯作者: 袁耀锋 E-mail:yaofeng_yuan@fzu.edu.cn
基金资助:
国家基础科学人才培养基金(No. J1103303)、中国科学院福建物质结构研究所结构化学国家重点实验室(No. 20120010)资助项目.

Design, Synthesis and Anion Recognition of Benzocoumarin-Based Thiourea Receptors

Yan Xiquan^a, Zhuo Jibin^a, Wang Jicheng^a, Xie Lili^a,b, Yuan Yaofeng^a,b

a College of Chemistry, Fuzhou University, Fuzhou 350116;
b State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002

Received:2015-05-26 Revised:2015-06-12 Published:2015-06-19
Supported by:
Project supported by the National Natural Science Foundation of China (No. J1103303), the State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences (No. 20120010).

1. Design, Synthesis and Anion Recognition of Benzocoumarin-Based Thiourea Receptors.PDF(940KB)

Abstract

Anions display a great significant role in the environment and life science. The design and synthesis of receptors with high selective recognition anion has attracted considerable attention. The selective identification fluoride anion of benzocoumarin-based thiourea receptors 4a～4e were obtained starting from β-naphthol by a multi-step reaction. Their structures were characterized by ¹H NMR, ¹³C NMR, IR and elemental analysis. The interactions between receptors 4a～4e and anions (F^-, AcO^-, C1^-, Br^-, I^-, HSO₄^-) were studied by optical (UV-Vis absorption and fluorescence) and ¹H NMR spectroscopy. The results showed that the receptors with anion through hydrogen bonds formed stable 1:2 complexes, which leaded to the change spectroscopy of receptor molecules. Determination of the combined ratio and the stability constants of complexes were borne out receptor molecules with high alternative recognition F^- or AcO^- anions with limit of detect of 5.45 and 7.00 μg/L and the effect of reaction time of 5 min and 10 min respectively. However, there is no selectively responds to other anions. Using NMR titration and theoretical (B3LYP/6-31G (d, p)) methods further confirmed the hydrogen bond acceptor molecules and anions.

Key words: benzo coumarin, thiourea, anion recognition, hydrogen bond

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Yan Xiquan, Zhuo Jibin, Wang Jicheng, Xie Lili, Yuan Yaofeng. Design, Synthesis and Anion Recognition of Benzocoumarin-Based Thiourea Receptors[J]. Chin. J. Org. Chem., 2015, 35(10): 2184-2190.

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苯并香豆素硫脲类受体分子的设计、合成与阴离子识别研究

Design, Synthesis and Anion Recognition of Benzocoumarin-Based Thiourea Receptors

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