超分子有机框架对分子容器的水相增溶的梯度增强效应

doi:10.6023/cjoc202202038

有机化学 ›› 2022, Vol. 42 ›› Issue (7): 2236-2242.DOI: 10.6023/cjoc202202038 上一篇下一篇

研究论文

超分子有机框架对分子容器的水相增溶的梯度增强效应

王泽坤^a, 徐子悦^a, 李娟娟^b, 余尚博^c, 王辉^a, 郭东升^b, 张丹维^a, 黎占亭^a^,^c^,^*()

^a复旦大学化学系上海市分子催化和功能材料重点实验室上海 200438
^b南开大学化学学院元素有机化学国家重点实验室天津 300071
^c中国科学院上海有机化学研究所有机功能分子合成与组装化学重点实验室上海 200032

收稿日期:2022-02-28 修回日期:2022-03-13 发布日期:2022-08-09
通讯作者: 黎占亭
基金资助:
国家自然科学基金(21921003); 国家自然科学基金(21890730); 国家自然科学基金(21890732)

Gradient Enhancement of Supramolecular Organic Framework for Solubilization of Hydrophobic Molecules by Two Molecular Containers in Water

Ze-Kun Wang^a, Zi-Yue Xu^a, Juan-Juan Li^b, Shang-Bo Yu^c, Hui Wang^a, Dong-Sheng Guo^b, Dan-Wei Zhang^a, Zhan-Ting Li^a^,^c()

^aDepartment of Chemistry, Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Fudan University, Shanghai 200438
^bCollege of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071
^cKey Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2022-02-28 Revised:2022-03-13 Published:2022-08-09
Contact: Zhan-Ting Li
Supported by:
National Natural Science Foundation of China(21921003); National Natural Science Foundation of China(21890730); National Natural Science Foundation of China(21890732)

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摘要/Abstract

很多功能性有机分子在水中溶解度很小, 限制了它们的实际应用. 水溶性主体的包结是提高有机分子水溶性的重要手段, 但要获得显著的增溶效果, 一般需要主体分子具有很高的浓度. 报道了一种梯度增溶新策略, 即利用一种高水溶性多孔聚合物富集另一个具有增溶作用的主体分子, 提高其局部有效浓度, 实现其增溶作用增强的目的. 为此利用一个水溶性正离子型超分子有机框架, 吸收富集负离子型杯[5]芳烃, 实现了杯[5]芳烃对C₆₀、C₇₀、二茂铁、1,1'-二甲二茂铁及1,1°-二溴二茂铁的增溶作用的进一步提高, 通过吸收富集开环葫芦脲, 实现了后者对紫杉醇, 多西他赛和卡巴他赛的水溶性的进一步提高.

关键词: 超分子有机框架, 主-客体化学, 杯芳烃, 开环葫芦脲, 梯度增溶, 富勒烯, 二茂铁, 紫杉醇

Many functional organic molecules have very low water-solubility, which remarkably limits their practical applications. The inclusion of water-soluble hosts has been demonstrated as an important strategy to increase the water solubility of organic molecules. However, this strategy usually requires high concentration for the hosts to realize efficient solubilization of guest molecules. Herein a new strategy of gradient solubilization by utilizing a water-soluble porous supramolecular polymer to adsorb or enrich molecular containers to increase their efficient concentration in a confined space is reported. For this aim, a cationic water-soluble supramolecular organic framework was used to include an anionic calix[5]arene or an anionic acyclic cucurbituril. In this way, the supramolecular organic framework was revealed to exhibit significant gradient enhancement for the solubilization of the calix[5]arene host for C₆₀, C₇₀, ferrocene, 1,1'-dimethylferrocene and 1,1'-dibromoferrocene, and the solubilization of the acyclic cucurbituril host for paclitaxel, docetaxel and cabazitaxel.

Key words: supramolecular organic framework, host-guest chemistry, calixarene, acyclic cucurbituril, gradient solubilization, fullerene, ferrocene, paclitaxel

引用此文

王泽坤, 徐子悦, 李娟娟, 余尚博, 王辉, 郭东升, 张丹维, 黎占亭. 超分子有机框架对分子容器的水相增溶的梯度增强效应[J]. 有机化学, 2022, 42(7): 2236-2242.

Ze-Kun Wang, Zi-Yue Xu, Juan-Juan Li, Shang-Bo Yu, Hui Wang, Dong-Sheng Guo, Dan-Wei Zhang, Zhan-Ting Li. Gradient Enhancement of Supramolecular Organic Framework for Solubilization of Hydrophobic Molecules by Two Molecular Containers in Water[J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2236-2242.

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图/表 5

图1. 化合物T1和CB[8]组装SOF-1, 及化合物M1、CLX和ACB的结构

Figure 1. Formation of SOF-1 from T1 and CB[8], and the structures of compounds T1, CB[8], M1, CLX and ACB

图2. SOF-1 ([T1]=62.5 μmol/L)水溶液的荧光光谱(450 nm, 25 °C)随(a) CLX和(b) ACB加入的变化

Figure 2. Change of the fluorescence spectra (450 mmol/L) of SOF-1 ([T1]=62.5 μmol/L) with the addition of (a) CLX and (b) ACB in water at 25 °C [Anion]: the anionic concentration of CLX and ACB, [Cation]: the cationic concentration of monomer T1 in SOF-1

图3. SOF-1组装体的电动电位与[客体负离子]/[组装体正离子]的关系图

Figure 3. Zeta potential of SOF-1 versus [Anion]/[Cation] [Anion] and [Cation] represent the ionic concentration of CLX, ACB or SOF-1

图4. SOF-1 ([T1]=5 mmol/L)/CLX (1 mmol/L)混合水溶液及其与饱和的(a) C60或(b) C70的溶液 (25 °C)的紫外-可见吸收谱

Figure 4. UV-Vis spectra of the solutions of SOF-1 ([T1]=5 mmol/L) and CLX (1 mmol/L) and their mixtures with saturated (a) C60 or (b) C70 in water at 25 °C

图5. (a) C60、C70、二茂铁(Fc)、1,1'-二甲基二茂铁(DFc)和1,1'-二溴二茂铁(DBFc)在SOF-1 ([T1]=5.0 mmol/L)/CLX (1.0 mmol/L)体系、T1 (5.0 mmol/L)/CLX (1.0 mmol/L)体系、SOF-1 ([T1]=5.0 mmol/L)/PPSS(对羟基苯磺酸钠, 5.0 mmol/L)体系和NaCl(40 mmol/L)/CLX (1.0 mmol/L)体系中的溶解度, 以及(b)紫杉醇(PTX)、多西他赛(DTX)、卡巴他赛(CTX)在SOF-1 ([T1]=0.5/ACB (0.5 mmol/L)体系、ACB (1.0 mmol/L)体系、纯水体系中的溶解度

Figure 5. (a) Solubility of C60, C70, ferrocene (Fc), 1,1'-dimethylferrocene (DMFc) and 1,1'-dibromoferrocene (DBFc) in the aqueous solutions of SOF-1 ([T1]=5.0 mmol/L)/CLX (1.0 mmol/L), T1 (5.0 mmol/L)/CLX (1.0 mmol/L), SOF-1 ([T1]=5.0 mmol/L)+PPSS (p-phenolsulfonic sodium, 5.0 mmol/L) and NaCl (40 mmol/L)/CLX (1.0 mmol/L). (b) Solubility of Paclitaxel (PTX), Docetaxel (DTX), Cabazitaxel (CTX) in SOF-1 ([T1]=0.5 mmol/L)/ACB (0.5 mmol/L), ACB (1.0 mmol/L) and water

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超分子有机框架对分子容器的水相增溶的梯度增强效应

Gradient Enhancement of Supramolecular Organic Framework for Solubilization of Hydrophobic Molecules by Two Molecular Containers in Water

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