Pattern and Protonation Effect of Benzene Dicarboxylate Anion Species in Self-assembly System

doi:10.6023/A14010029

Acta Chimica Sinica ›› 2014, Vol. 72 ›› Issue (4): 447-455.DOI: 10.6023/A14010029 Previous Articles Next Articles

Article

自组装中的苯二甲酸阴离子形貌及质子化效应

周丽^a, 徐立进^a, 龚汉元^b

a 中国人民大学化学系北京 100872;
b 北京师范大学化学学院北京 100875

投稿日期:2014-01-10 发布日期:2014-02-06
通讯作者: 徐立进 E-mail：xulj@chem.ruc.edu.cn;龚汉元 E-mail：hanyuangong@bnu.edu.cn E-mail:xulj@chem.ruc.edu.cn;hanyuangong@bnu.edu.cn
基金资助:
项目受国家自然科学基金（Nos.21202199，21372258）资助.

Pattern and Protonation Effect of Benzene Dicarboxylate Anion Species in Self-assembly System

Zhou Li^a, Xu Lijin^a, Gong Hanyuan^b

a Department of Chemistry, Renmin University of China, Beijing 100872;
b College of Chemistry, Beijing Normal University, Beijing 100875

Received:2014-01-10 Published:2014-02-06
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21202199, 21372258).

1. Pattern and Protonation Effect of Benzene Dicarboxylate Anion Species in Self-assembly System.PDF(166KB)

Abstract

A novel macrocycle host with flexible structure and big cavity, cyclo[2](2,6-bis(1H-imidazol-1-yl)- pyridine)[2](1,4-dimethylenebenzene) (i.e. 1⁴⁺), was effectively synthesized through cyclization reaction between 1,4-bisbromo-methylbenzene and 2,6-di(1H-imidazol-1-yl)pyridine. The binding and self-assembly properties of macrocycle host 1⁴⁺ with a series of benzene dicarboxylate anion guests (i.e. mono-terephthalate anion 2, di-terephthalate anion 3, mono-isophthalate anion 4, di-isophthalate anion 5, mono-phthalate anion 6 or di-phthalate anion 7) were studied in detail via ¹H NMR spectroscopy, diffusion ordered NMR spectroscopy (DOSY), nuclear Overhauser effect spectroscopy (NOESY) in solution, electrospray ionization mass spectrometry (ESI-MS) in gas phase, and X-ray single crystallography in solid state. The result implied that macrocycle host 1⁴⁺ and mono-terephthalate anion (2) or di-isophthalate anion (5) form pseudorotaxane structure, even more complex supramolecular self-assembly structure (e.g. pseudo-oligarotaxne ). Meanwhile the other guest anions adopt the "outside" binding modes in the complexation with 1⁴⁺. It is also found that the thermodynamic equilibrium(s) and association constants of the complexes between macrocycle host 1⁴⁺ and a series of benzene dicarboxylate anion guest species are different via ¹H NMR Job-plots and ¹H NMR spectroscopic titrations in solution: (1) the stoichiometry values suggested that host 1⁴⁺ can bind equivalent or more mono-anion guests than di-anion species from the same benzene dicarboxylic acid; (2) comparing the association constants of 1:1 (host:guest) complex between 1⁴⁺ and mono-anion species resulted in K_a[1⁴⁺·2]>K_a[1⁴⁺·4]>K_a[1⁴⁺·6]; the similar comparison was carried out for di-anion species interactions and obtained K_a[1⁴⁺·3]>K_a[1⁴⁺·5]>K_a[1⁴⁺·7]; the result suggest that the pattern of the anion highly influences the thermostability of the 1:1 complex. It is speculated that the pattern and protonation factors of the benzene dicarboxylate anion guests determine their interactions with macrocycle 1⁴⁺, including binding modes, stoichiometries, association constants, and so on. The finding will help to direct the following novel supramolecular self-assembly construction involving macrocycle host and multi-carboxylate anion species.

Key words: macrocylic host compound, benzene dicarboxylate anions, host-guest chemistry, non-covalent weak interactions, complexation mode

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Zhou Li, Xu Lijin, Gong Hanyuan. Pattern and Protonation Effect of Benzene Dicarboxylate Anion Species in Self-assembly System[J]. Acta Chimica Sinica, 2014, 72(4): 447-455.

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自组装中的苯二甲酸阴离子形貌及质子化效应

Pattern and Protonation Effect of Benzene Dicarboxylate Anion Species in Self-assembly System

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