SIOC English
有机化学
高级检索

有机化学 >

2024 , Vol. 44 >Issue 1: 277 - 281

DOI: https://doi.org/10.6023/cjoc202306013

研究论文

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
展开
  • 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
†共同第一作者.

收稿日期: 2023-06-18

  修回日期: 2023-07-21

  网络出版日期: 2023-08-30

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)

收起

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
Expand
  • Guangxi Key Laboratory of Agricultural Resources Chemistry and Biotechnology, College of Chemistry and Food Science, Yulin Normal University, Yulin, Guangxi 537000
†These authors contributed equally to this work.
*E-mail: ;
E-mail:

Received date: 2023-06-18

  Revised date: 2023-07-21

  Online published: 2023-08-30

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)

Fold

摘要

以蒽为原料, 通过一系列有机反应高效合成了三种不同的含双硫脲基团的分子钳化合物, 通过熔点, 1H NMR, 13C NMR和HRMS进行结构表征和确证, 并采用荧光光谱法详细研究了分子钳在非极性环境下对几种中性分子的识别行为. 测试结果表明, 分子钳9,10-二(3,5-三氟甲基苯基-硫脲)蒽(T-3)对几种客体分子有较好的识别能力. 详细讨论了分子间氢键与多种C—H…π相互作用力在分子识别中的协同作用.

关键词： 双硫脲分子钳; 合成; 识别; 中性分子

本文引用格式

陈珊 , 陈志林 , 胡琼 , 蒙艳双 , 黄悦 , 陶萍芳 , 卢丽如 , 黄国保 . 含双硫脲基团分子钳在非极性溶剂中识别中性分子[J]. 有机化学, 2024 , 44(1) : 277 -281 . DOI: 10.6023/cjoc202306013

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

参考文献

[1]
Berthod, A. Anal. Chem. 2006, 78, 2093.
[2]
Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7017.
[3]
Zhao, Z.-G.; Liu, X.-L.; Li, Q.-H.; Chen, S.-H. Chin. J. Org. Chem. 2009, 29, 1336 (in Chinese).
[3]
(赵志刚, 刘兴利, 李清寒, 陈淑华, 有机化学, 2009, 29, 1336.)
[4]
Salonen, L. M.; Ellermann, M.; Diederich, F. Angew. Chem., Int. Ed. 2011, 50, 4808.
[5]
Chen, C.-W.; Whitlock Jr., H. W. J. Am. Chem. Soc. 1978, 100, 4921.
[6]
Hardouin-Lerouge, M.; Hudhomme, P.; Salle, M. Chem. Soc. Rev. 2001, 40, 30.
[7]
Legouin, B.; Uriac, P.; Tomasi, S.; Toupet, L.; Bondon, A.; Vande Weghe, P. Org. Lett. 2009, 11, 745.
[8]
Colquhoun, H. M.; Zhu, Z.; Williams, D. J. Org. Lett. 2003, 5, 4353.
[9]
Canevet, D.; Sallé, M.; Zhang, G.; Zhang, D.; Zhu, D. Chem. Commun. 2009, 2245.
[10]
(a) Park, J.-S.; Le Derf, F.; Bejger, C.-M.; Lynch, V.-M.; Sessler, J.-L.; Nielsen, K.-A.; Johnsen, C.; Jeppesen, J.-O. Chem.-Eur. J. 2010, 16, 848.
[10]
(b) Dolensky, B.; Havlík, M.; Král, V. Chem. Soc. Rev. 2012, 41, 3839.
[10]
(c) Zimmerman, S. Beilstein J. Org. Chem. 2016, 12, 125.
[10]
(d) Kumar, R.; Srivastava, A. Chem.-Eur. J. 2016, 22, 3224.
[10]
(e) Fu, T.; Han, Y.; Ao, L.; Wang, F. Organometallics 2016, 35, 2850.
[10]
(f) Tsuchido, Y.; Suzaki, Y.; Ide, T.; Osakada, K. Chem.-Eur. J. 2014, 20, 4762.
[11]
(a) Gunnlaugsson, T.; Davis, A. P.; O'Briena, J. E.; Glynna, M. Org. Biomol. Chem. 2005, 3, 48.
[11]
(b) Zhang, Z.-Y.; Li, C. Acc. Chem. Res. 2022, 55, 916.
[11]
(c) Zhang, X; Wang, X.; Wang, B.; Ding, Z.; Li, C. Chin. Chem. Lett. 2020, 31, 3230.
[12]
(a) Huang, G.; He, Z.; Cai, C.; Pan, F.; Yang, D.; Rissanen, K.; Jiang, W. Chem. Commun. 2015, 15, 15490.
[12]
(b) Huang, G.; Valkonen, A.; Rissanen, K.; Jiang, W. Chem. Commun. 2016, 52, 9078.
[13]
Altava, B.; Burguete, M. I.; Escuder, B.; Luis, S. V.; García-Espa?a, E.; Mu?oz, M. C. Tetrahedron 1997, 53, 2629.
Options
文章导航

/

〈 〉