Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent

doi:10.6023/cjoc202306013

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (1): 277-281.DOI: 10.6023/cjoc202306013 Previous Articles Next Articles

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含双硫脲基团分子钳在非极性溶剂中识别中性分子

陈珊, 陈志林, 胡琼, 蒙艳双, 黄悦, 陶萍芳^*(), 卢丽如, 黄国保^*()

玉林师范学院化学与食品科学学院广西农产资源化学与生物技术重点实验室广西玉林 537000

收稿日期:2023-06-18 修回日期:2023-07-21 发布日期:2023-08-30
作者简介:
^†共同第一作者.
基金资助:
国家自然科学基金(21961042); 及玉林师范学院科研(G2021ZK16); 玉林师范学院高层次人才(G2023ZK12); 及玉林师范学院科研(S202210606118)

Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent

Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao(), Liru Lu, Guobao Huang()

Guangxi Key Laboratory of Agricultural Resources Chemistry and Biotechnology, College of Chemistry and Food Science, Yulin Normal University, Yulin, Guangxi 537000

Received:2023-06-18 Revised:2023-07-21 Published:2023-08-30
Contact: *E-mail: lzjx0915@163.com; E-mail: 506658201@qq.com
About author:
^†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21961042); Program of Yulin Normal University(G2021ZK16); Yulin Normal University High-Level Talent Project(G2023ZK12); Program of Yulin Normal University(S202210606118)

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Abstract

Three different molecular tweezers containing bis-thiourea groups were efficiently synthesized by a series of organic reactions using anthracene as raw materials. Their structures were confirmed and characterized by melting point, ¹H NMR, ¹³C NMR and HRMS. The recognition behavior of molecular tweezers to several neutral molecules in non-polar environment was studied in detail by fluorescence spectroscopy. The results show that the molecular tweezer 9,10-bis- trifluoromethylphenyl-thioureamethyl anthracene (T-3) has good recognition ability for several guest molecules, and the synergistic effect between the hydrogen bonding and multiple C—H…π interactions on molecular recognition was discussed.

Key words: bis-thiourea tweezer, synthesis, recognition, neutral molecule

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Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent[J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.

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Fig. & Tab. 5

Scheme 1. Synthesis route of bis-thiourea tweezers

Figure 1. Changes in the fluorescence emission spectra of T-1 in CHCl3 upon addition of G1 ([G1] 0~500 mmol/L)

Figure 2. Titration data graph between host and guest obtained by nonlinear fitting

Figure 3. Structures of the guests

Host	T-1	T-2	T-3
G1	3560±96	2953±350	4811±510
G2	2450±171	1995±78	3921±256
G3	997±75	776±40	1847±176
G4	2989±66	2824±149	4200±352
G5	1178±74	833±42	2197±144
G6	1380±40	939±47	2318±99

Table 1. Binding constants [Ka/(L?mol－1)] between host and guest determined by fluorescence titration

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含双硫脲基团分子钳在非极性溶剂中识别中性分子

Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent

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