均苯四甲酸二酰亚胺拓展柱[6]芳烃与羧酸盐客体分子的络合性能研究

doi:10.6023/cjoc202206018

有机化学 ›› 2023, Vol. 43 ›› Issue (1): 352-356.DOI: 10.6023/cjoc202206018 上一篇下一篇

研究简报

均苯四甲酸二酰亚胺拓展柱[6]芳烃与羧酸盐客体分子的络合性能研究

程璐^a, 曾飞^b^,^*(), 王小峰^a^,^*()

a 南华大学化学化工学院湖南衡阳 421001
b 湖南科技学院化学与生物工程学院湖南永州 425199

收稿日期:2022-06-13 修回日期:2022-07-22 发布日期:2022-08-17
通讯作者: 曾飞, 王小峰
基金资助:
国家自然科学基金(21602055)

Study on the Complexation Properties of Promellitic Diimide- Extended Pillar[6]aren and Carboxylate Guests

Lu Cheng^a, Fei Zeng^b(), Xiaofeng Wang^a()

a School of Chemistry and Chemical Engineering, University of South China, Hengyang, Hunan 421001
b College of Chemical and Biological Engineering, Hunan University of Science and Engineering, Yongzhou, Hunan 425199

Received:2022-06-13 Revised:2022-07-22 Published:2022-08-17
Contact: Fei Zeng, Xiaofeng Wang
Supported by:
National Natural Science Foundation of China(21602055)

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摘要/Abstract

描述了均苯四甲酸二酰亚胺拓展柱[6]芳烃主体与羧酸盐客体分子在溶液中的络合性质, 表明缺电子的主体分子与富电子的羧酸盐客体分子, 通过分子间的弱相互作用力能够形成1∶2的超分子络合物. 此外, 主客体络合物的形成与解离具有酸碱的环境响应性, 并且该过程也可通过肉眼进行观察.

关键词: 柱芳烃, 均苯四甲酸二酰亚胺, 酸碱调控, 主客体化学

The complexation between the pyromellitic diimide-extended pillar[6]aren host and carboxylate guests in solution was investigated in detail. It was found that the host could form 1∶2 complexes with carboxylate salts in solution. Interestingly, the complexation and decomplexation of the complexes between the host and the guest could be achieved by changing the pH of the solution, and the process could also be observed by naked eye.

Key words: pillararen, pyromellitic diimide, acid-base controlled, host-guest chemistry

引用此文

程璐, 曾飞, 王小峰. 均苯四甲酸二酰亚胺拓展柱[6]芳烃与羧酸盐客体分子的络合性能研究[J]. 有机化学, 2023, 43(1): 352-356.

Lu Cheng, Fei Zeng, Xiaofeng Wang. Study on the Complexation Properties of Promellitic Diimide- Extended Pillar[6]aren and Carboxylate Guests[J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 352-356.

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图/表 6

图1. 主体1与客体G1~G5的结构、质子信号标注以及1的静电势图

Figure 1. Chemical structures and proton designations of host 1 and guests G1~G5, and calculated potential profile of 1

图2. 室温下在CDCl3中的部分氢谱图(400 MHz)

Figure 2. Partial 1H NMR spectra (400 MHz, 298 K) in CDCl3 (a) Free 1, (b) 1 and 2.0 equiv. of G1, and (c) free G1. [1]0=4.0 mmol/L

图3. 室温下在CDCl3中的部分氢谱图(400 MHz).

Figure 3. Partial 1H NMR spectra (400 MHz, 298 K) in CDCl3 (a) Free 1, (b) 1 and 2.0 equiv. of G4, and (c) free G4. [1]0=4.0 mmol/L

Complex	Stoichiometry (H/G)	K_a1/(L•mol^–1)	K_a2/(L•mol^–1)	Cooperativity factor α^a
1•2G₁	1∶2	(2.68±0.04)×10⁴	(0.08±0.05)×10²	0.001
1•2G₂	1∶2	(2.33±0.09)×10⁴	(0.38±0.09)×10²	0.007
1•2G₃	1∶2	(3.26±0.03)×10³	(0.18±0.02)×10²	0.022
1•2G₄	1∶2	(8.20±0.58)×10²	(1.10±0.11)×10²	0.537
1•2G₅	1∶2	(3.78±0.25)×10³	(2.68±0.05)×10³	2.836

表1. 络合物的化学计量比以及络合常数

Table 1. Summary of the stoichiometries and association constants of the complexes

图4. 部分1H NMR谱(400 MHz, CDCl3, 298 K)和照片

Figure 4. Partial 1H NMR spectra (400 MHz, 298 K) in CDCl3 (a) 1 and 2.0 equiv. of G1, (b) after addition of 2.0 μL of DCl (w=20%) to a, and (c) after addition of 1.0 μL of NaOD (w=40%) to b. [1]0=4.0 mmol/L

图5. 经过Gaussian 09软件优化后络合物1?2G2的结构

Figure 5. Structure of 1?2G2 optimized by Gaussian 09

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均苯四甲酸二酰亚胺拓展柱[6]芳烃与羧酸盐客体分子的络合性能研究

Study on the Complexation Properties of Promellitic Diimide- Extended Pillar[6]aren and Carboxylate Guests

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