刺激响应型树状分子凝胶的研究进展※

doi:10.6023/A22080363

化学学报 ›› 2022, Vol. 80 ›› Issue (10): 1424-1435.DOI: 10.6023/A22080363 上一篇下一篇

所属专题：中国科学院青年创新促进会合辑

综述

刺激响应型树状分子凝胶的研究进展^※

刘志雄^a^,^*(), 初庆凯^a, 冯宇^b^,^*()

a 山西大同大学化学与化工学院大同 037009
b 常州大学材料科学与工程学院常州 213164

投稿日期:2022-08-19 发布日期:2022-09-14
通讯作者: 刘志雄, 冯宇

作者简介:

刘志雄, 理学博士, 山西大同大学副教授, CSCP海洋污损防护技术专业委员会委员, 2014 年于中国科学院化学研究所获得理学博士学位, 2015～2019年在中国科学院宁波材料技术与工程研究所从事博士后研究, 2019年初调动至山西大同大学化学与化工学院工作至今, 主要研究方向包括: (1)高分子智能凝胶材料; (2)表界面功能材料. 主持了国家自然科学青年基金, 中国博士后科学基金特别资助、中国博士后科学基金面上资助, 宁波市“科技创新2025”重大专项等科研攻关项目10余项, 在Chem, Bi-omacromolecules, Chem. Mater.,和 Chem. Eng. J.等国际著名专业杂志发表研究论文30余篇, 授权国家发明专利6项.

初庆凯, 山西大同大学在读硕士研究生, 主要研究方向: 功能化凝胶材料在金属离子检测、吸附领域中的应用研究.

冯宇, 博士, 常州大学材料科学与工程学院教授. 中国科学院青年创新促进会会员、优秀会员. 2010年于中国科学院化学研究所获得理学博士学位, 同年留所工作, 任助理研究员、副研究员, 2016年10月至2018年1月期间在日本北陆先端科学技术大学院大学开展访问研究. 2022年初调动至常州大学材料科学与工程学院工作至今. 主要研究方向包括: (1)功能超分子凝胶; (2)手性功能分子的设计合成、组装及圆偏振发光性能研究; (3)不对称催化. 截至目前, 以项目负责人身份主持国家自然科学基金、中国科学院和中国科学院化学研究所等科研和人才项目10余项. 在Chem. Soc. Rev., Acc. Chem. Res., J. Am. Chem. Soc., Angew. Chem. Int. Ed.等期刊上发表SCI论文50余篇.

^※ 庆祝中国科学院青年创新促进会十年华诞.

基金资助:
国家自然科学基金(21871270); 国家自然科学基金(21472192); 山西大同大学博士启动基金(2019-B-01); 山西大同自然科学项目(2020YGZX011); 中国科学院海洋新材料与应用技术重点实验室开放基金(2021K02)

Progress in Stimulus-Responsive Dendritic Gels^※

Zhixiong Liu^a(), Qingkai Chu^a, Yu Feng^b()

a School of Chemistry and Chemical Engineering, Shanxi Datong University, Datong 037009, China
b School of Materials Science and Engineering, Changzhou University, Changzhou 213164, China

Received:2022-08-19 Published:2022-09-14
Contact: Zhixiong Liu, Yu Feng
About author:
^※ Dedicated to the 10th anniversary of the Youth Innovation Promotion Association, CAS.
Supported by:
National Natural Science Foundation of China(21871270); National Natural Science Foundation of China(21472192); Doctor Research Fund of Shanxi Datong University(2019-B-01); Science Foundation of Shanxi Datong University(2020YGZX011); Open Research Fund of Key Laboratory of Marine Materials and Related Technologies, CAS(2021K02)

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摘要/Abstract

近年来, 刺激响应型超分子凝胶作为一类智能软物质材料, 在离子识别材料、自修复材料、生物材料和药物缓释等领域展现出了非常好的应用前景, 受到人们广泛关注. 树状分子是一类具有高度支化结构的大分子, 其形成的凝胶兼具有机小分子凝胶和聚合物凝胶的双重优点, 树状分子丰富的多层次支化几何结构有利于修饰不同功能基团, 从而确保各功能基团彼此独立作用而不相互干扰, 这种特性使其在构筑多功能化凝胶材料, 尤其是多重环境刺激响应型凝胶材料方面具有独特优势. 基于此, 本综述从树状分子凝胶因子设计、成凝胶机理、响应性能和响应机理等方面详细归纳了刺激响应型树状分子凝胶的研究进展. 按照刺激源不同, 主要从光响应型、氧化还原响应型、离子响应型、触变响应型和多重响应型五个方面对刺激响应树状分子凝胶进行了系统归纳总结. 最后, 基于目前刺激响应树状分子凝胶存在的一些问题对该领域未来发展进行了展望.

关键词: 超分子凝胶, 树状分子, 刺激响应, 智能材料, 进展

In recent years, stimulus-responsive supramolecular gels, as a class of smart soft matter materials, have shown very promising applications in the fields of ion recognition materials, self-healing materials, biomaterials and drug release, and have attracted increasing attentions. Dendrimers and dendrons are highly branched macromolecules with well-defined molecular architecture and have been widely used as building blocks in the self-assembling of supramolecular gel-phase materials. The unique dendritic architectures make the dendritic molecules as ideal candidates to be modified with various different functional moieties to develop multiple functional soft materials, which ensure each functionality to work independently without interfering. This characteristic makes them show unique advantages in the construction of stimuli- responsive gels, especially multiple stimuli-responsive gels. The research progress of stimuli-responsive dendritic gels is summarized in detail from the aspects of dendritic gel design, gel-formation mechanism, response performance and response mechanism. Based on the different stimulus, the stimulus-responsive dendritic gels are classfied into the following categories: light-responsive dendritic gel, redox-responsive dendritic gel, ion-responsive dendritic gel, thixotropic-responsive dendritic gel and multiple-responsive dendritic gel. In addition, the current challenges and perspectives on stimulus-responsive dendritic gels are also discussed.

Key words: supramolecular gels, dendrimer, stimuli-responsive, smart materials, progress

引用此文

刘志雄, 初庆凯, 冯宇. 刺激响应型树状分子凝胶的研究进展^※[J]. 化学学报, 2022, 80(10): 1424-1435.

Zhixiong Liu, Qingkai Chu, Yu Feng. Progress in Stimulus-Responsive Dendritic Gels^※[J]. Acta Chimica Sinica, 2022, 80(10): 1424-1435.

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图/表 24

图1. 首例树状分子水凝胶因子1和有机凝胶因子2的分子结构式

Figure 1. The structures of first example for dendritic hydrogelator 1 and organogelator 2

图2. (a)核心偶氮苯修饰的聚(谷氨酸-天冬氨酸)型树状分子凝胶因子3结构式; (b)光照前后凝胶-溶液转变示意图(乙酸乙酯, 0.1% (w))

Figure 2. (a) The structure of focal azobenzene modified poly(Gly-Asp) dendron 3; (b) schematic diagram of gel-solution transition before and after illumination (ethyl acetate, 0.1% (w))

图3. (a)不对称双嵌段树状分子凝胶因子4的化学结构式; (b, c)紫外光照前后凝胶-溶液转变图(环己烷, 0.05% w/V); (d, e)凝胶和溶液态时相对应的SEM图

Figure 3. (a) The chemical structure of asymmetric bis-dendritic gelator 4; photographs of the cyclohexane gel of 4 (0.05% w/V) (b) before and (c) after UV irradiation; the corresponding SEM images from the (d) gel state and (e) solution state

图4. (a)树状分子凝胶因子5和(b)主客体复合物5/α-CD的凝胶照片和可逆相变示意图. 两个体系中凝胶因子5的浓度为0.41% (w), 凝胶因子5/α-CD的物质的量比例为1∶1

Figure 4. Photographs of the gels and illustration of the reversible phase transitions of (a) dendritic gelator 5 and (b) host-guest inclusion supra- dendron 5/α-CD. The concentration of 5 gelator was 0.41% (w) in both cases, the 5/α-CD molar ratio was 1∶1

图5. (a)螺吡喃修饰的聚苄醚型树状分子6的分子结构式; (b)树状分子6组装形成囊泡和有机凝胶中网络结构的示意图, 以及在紫外和可见光照射下的相应转变和相应的CLSM图

Figure 5. (a) The chemical structure of spiropyran-functionalized dendron 6; (b) schematic representation of the self-assembly of dendron 6 into particles and network structure within the organogel, and the corresponding transformations under UV and visible irradiation as well as the corresponding CLSM images

图6. 核心修饰有蒽和对硝基肉桂酸官基团的树状分子凝胶因子7和8

Figure 6. Anthracene and p-nitrocinnamate modified dendritic hydrogelator 7 and organogelator 8

图7. (a)核心修饰有四硫富瓦烯(TTF)和单吡咯并四硫富瓦烯(MPTTF)聚芳醚型树状分子凝胶因子9~11的分子结构式; (b) 9/四氯苯醌双组分凝胶氧化还原响应示意图(30 mg•mL-1, 苯/乙腈, 1∶1, V/V): 添加Sc(CF3SO3)3后形成溶液照片, 添加镁条并经加热冷却形成凝胶

Figure 7. (a) The chemical structures of tetrathiafulvalene (TTF) and monopyrrolotetrathiafulvalene (MPTTF) cored poly(aryl ether) dendron 9~11; (b) the photographs of the two-component dendritic organogels formed by 9/chloranil (30 mg•mL-1, benzene/acetonitrile, 1∶1, V/V): the solution formed after addition of Sc(CF3SO3)3; the recovery of the gel phase after further stirring with magnesium strips, followed by heating and cooling

图8. (a)二茂铁功能化聚芳醚型树状分子凝胶因子12和13的化学结构式; (b)凝胶12 (4 mg•mL-1, CH3CN/THF)以及添加CAN后转变成溶液照片; (c)添加CAN前(黑)后(红)凝胶体系的紫外可见吸收光谱

Figure 8. (a) The chemical structures of ferrocene-based dendron gelators 12 and 13; (b) the photographs of the organogel 12 (4 mg•mL-1, CH3CN/THF) and the formed solution after adding with CAN; (c) the corresponding UV/Visible spectra of the dendritic organogel 12 in presence (red) and absence of CAN (black)

图9. 树状分子配体14的结构式和配体14与银离子配位形成的凝胶以及抗衡阴离子响应的照片

Figure 9. The chemical structure of dendritic ligand 14, and the photographs of the organogel formed by dendritic ligand 14 and silver ions as well as the formed solution upon counteranion exchange

图10. (a)基于聚(谷氨酸-天冬氨酸)和咔唑的树状分子凝胶因子15和16的分子结构式

Figure 10. The molecular structures of glycine-glutamic-acid and carbazole-based dendritic gelators 15 and 16

图11. (a)核心修饰有萘、蒽、芘官能团的AB3型聚芳醚型树状分子凝胶因子17~22的分子结构式

Figure 11. The molecular structures of the naphthalene, anthracene, pyrene cored AB3 type poly(aryl ether) dendritic gelators 17~22

图12. 凝胶17对氟离子响应的示意图(四氢呋喃, 4 mg•mL-1)

Figure 12. The pictures of organogel formed from 17 in THF (4 mg•mL-1) and after addition of F? (1 equiv.)

图13. (a)外围修饰有卤键给体的聚芳醚型树状分子凝胶因子24; (b)凝胶24(丙酮/正己烷, 1∶8, V/V, 12.0 mg•mL-1)对氯离子响应的示意图; (c, d)氯离子响应前后凝胶和溶液态时的SEM图; (e) 24-Cl-复合物的模拟结构图; (f) 24表面的电势分布图(蓝色部分表示带部分正电荷, 红色部分表示带部分负电荷)

Figure 13. (a) The chemical structure of halogen bond donor modified dendritic organogelator 24. (b) Photographs of the dendritic gel 24 in acetone/n-hexane mixed solvent (1∶8, V/V, 12.0 mg•mL-1) before and after the addition of chloride anion. SEM images of (c) the gel state and (d) the aggregate from the sol state after the addition of chloride anion. (e) Calculated structure of the 24-Cl- complex and (f) electrostatic potential surface of 24 (chloride-bound conformation, blue indicates sites of partial positive charge and red sites of partial negative charge)

图14. 大环金属配合物25~27对溴离子响应示意图

Figure 14. Schematic representation of bromide anion-responsive of discrete rhomboidal metallacyclic 25~27 gels

图15. 核心修饰有三联吡啶官能团AB3型聚芳醚型树状分子32

Figure 15. The chemical structure of terpyridine attached AB3 type poly(aryl ether) dendron 32

图16. (a)添加Pb2+后, 树状分子凝胶12 (CH3CN/THF, 4 mg•mL-1)凝胶态和溶液转变图以及添加OAc-后凝胶重新恢复的照片; (b)溶液态和(c)凝胶态时的SEM图

Figure 16. (a) The photographs of the gel-to-solution phase transition of the dendritic gel 12 (4 mg•mL-1) in CH3CN/THF triggered by addition of Pb2+ ion and the recovery of the gel phase after further addition of OAc-; the corresponding SEM images for (b) solution and (c) gel state

图17. 核心吡啶修饰的AB3型聚芳醚型树状分子33和34

Figure 17. The chemical structures of pyridine cored poly(aryl ether) dendrons 33 and 34

图18. “哑铃型”聚芳醚型树状分子凝胶因子35~40的化学结构式

Figure 18. The molecular structures of the 3,4-disubstituted twin-dendritic organogelators

图19. (a)外围间苯二甲酸二甲酯功能化聚芳醚型树状分子凝胶因子41和42的分子结构式; (b)凝胶42 (1,2-二氯乙烷, 6 mmol•L-1)的触变响应示意图; (c, d)凝胶42的流变力学性能表征(1,2-二氯乙烷, 15 ℃, 6 mmol•L-1): (c)应变扫描, (d)时间扫描

Figure 19. (a) Molecular structures of peripherally DMIP-functionalized poly(benzyl ether) dendrons 41 and 42; (b) reversible sol-gel phase transition of the gels of 42 in 1,2-dichloroethane gel (6 mmol•L-1) triggered by external mechanical stress; rheological data of 42 gel from 1,2-dichloroethane (15 ℃, 6 mmol•L-1): (c) strain amplitude sweeps, and (d) time sweep measurement

图20. 枝上修饰有偶氮苯官能团的聚芳醚型树状分子凝胶因子43的化学结构式及其多重外界刺激(如光、热、超声和应力)响应性能

Figure 20. The molecular structure of azo-functionalized poly(aryl ether) dendritic gelator 43 and reversible sol-gel phase transition of dendritic gelator 43, tuned by multiple stimuli (light, temperature, sonication, and shear stress)

图21. (a)树状分子凝胶因子44的化学结构式; (b)树状分子凝胶的多重外界刺激(如阴离子、热和触变)响应性能示意图

Figure 21. (a) The molecular structure of poly(aryl ether) dendritic gelator 44. (b) Reversible sol-gel phase transition of dendritic gelator 44, tuned by multiple stimuli (temperature, anions, and shear stress)

图22. 树状分子金属凝胶因子45和46的分子结构式

Figure 22. The molecular structures of poly(aryl ether) dendritic metallogelators 45 and 46

图23. (a)核心修饰有2-(2′-羟基苯基)苯并噁唑官能团的聚芳醚型树状分子凝胶因子47的化学结构式; (b)树状分子凝胶在多重化学刺激(如氟离子、锌离子和pH)和物理刺激(如热、超声和触变)作用下的凝胶态和溶液态照片

Figure 23. (a) The molecular structure of 2-(2'-hydroxyphenyl) benzoxazole cored poly(aryl ether) dendritic gelator 47. (b) Reversible sol-gel phase transition of dendritic gelator 47 tuned by multiple chemical stimulus (e.g. fluorine ion, zinc ions and pH value) and physical stimulus (e.g. temperature, sonication, and shear stress)

图24. 核心修饰有偶氮苯和喹啉官能团的聚芳醚型树状分子凝胶因子48和49的分子结构式

Figure 24. Molecular structures of azobenzene- and quinoline-cored poly(aryl ether) dendritic gelators 48 and 49

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刺激响应型树状分子凝胶的研究进展^※

Progress in Stimulus-Responsive Dendritic Gels^※

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刺激响应型树状分子凝胶的研究进展※

Progress in Stimulus-Responsive Dendritic Gels※

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刺激响应型树状分子凝胶的研究进展^※

Progress in Stimulus-Responsive Dendritic Gels^※