超分子聚集诱导发光材料的研究进展及展望

doi:10.6023/cjoc202305010

摘要/Abstract

通过超分子自组装构建发光材料是超分子化学研究的重要领域之一. 超分子自组装作为一种简单且高效的手段, 可以将不同结构的分子通过非共价键作用力构建成具有精确结构和多功能的组装体, 进一步赋予了超分子材料独特的物理特性. 由于超分子发光材料中非共价键相互作用力具有动态且可逆的性质, 因此使其具有对刺激物特异性识别和对微环境变化敏感的特点, 从而被广泛应用于生物传感和成像、药物传递、化学传感、人工光收集系统、信息加密和光催化等领域. 基于此, 为了了解超分子发光材料的最新研究进展, 主要按照氢键相互作用、π-π堆积和多种非共价键相互作用, 较系统地阐述了最近四年超分子发光材料, 从设计到制备再到应用的最新研究进展, 并且进一步展望了其未来所面临的挑战.

关键词: 超分子化学, 发光材料, 特异性识别, 非共价键

The construction of luminescent materials by supramolecular self-assembly is one of the important fields in supramolecular chemistry. Supramolecular self-assembly, as a simple and efficient strategy, can construct different types of molecules through non-covalent bonding, leading to the multifunctional assembly with precise structure, which further endows supramolecular materials with unique photophysical properties. Due to the dynamic and reversible nature of non-covalent bond interaction, supramolecular luminescence materials have the characteristics of specific recognition of stimuli and sensitivity to microenvironment changes, so they are widely used in the fields of biosensing and imaging, drug delivery, chemical sensing, artificial light collection system, information encryption and photocatalysis. Based on this, in order to understand the latest research progress of supramolecular luminescence materials, the latest research progress of supramolecular luminescence materials from design to preparation and application in the last four years is systematically described, mainly in terms of hydrogen bond interaction, π-π stacking and various non-covalent bond interactions. Its future challenges are prospected.

Key words: supramolecular chemistry, luminescent material, specific recognition, non-covalent bonding

引用此文

鲁会名, 马拉毛草, 马恒昌. 超分子聚集诱导发光材料的研究进展及展望[J]. 有机化学, 2023, 43(12): 4075-4105.

Huiming Lu, Lamaocao Ma, Hengchang Ma. Research Progress and Prospect of Aggregation-Induced Emission Supramolecular Luminescence Materials[J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4075-4105.

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图/表 30

图1. (a) PVP-BA&Py的合成; (b) TPA-Py, PVP-BA和PVP-BA&Py的激发/发射波长、荧光量子产率和在日光、紫外灯下的照片; (c)在25 ℃下用荧光球传感器检测鱼类腐败过程

Figure 1. (a) Synthesis of PVP-BA&Py; (b) Excitation/emission wavelengths of TPA-Py, PVP-BA, and PVP-BA&Py, fluorescence quantum yields and photographs under daylight and ultraviolet lamps; (c) Photographs of fish spoilage processes detected at 25 ℃ Reprinted with permission from Ref. [22], Copyright 2021, American Chemical Society.

图2. 基于UPy超分子聚合物和不同染料的人工LHS自组装

Figure 2. Self-assembly of an artificial LHS based on UPy supramolecular polymer and different dyes (a) Reprinted with permission from Ref. [23], Copyright 2020, The Royal Society of Chemistry; (b) and (c) Reprinted with permission from Ref. [24], Copyright 2021, The Royal Society of Chemistry.

图3. (a)超分子聚合物PVA(PTC4)x的化学结构; (b)芳基硼酸与聚乙烯醇掺杂制备的具有室温磷光现象的材料

Figure 3. (a) Chemical structure of supramolecular polymer PVA(PTC4)x; (b) Stimulation-responsive materials with room temperature phosphorescence prepared by doping arylboric acid with polyvinyl alcohol (a) Reprinted with permission from Ref. [25], Copyright 2020, The Royal Society of Chemistry; (b) Reprinted with permission from Ref. [26], Copyright 2020, the authors, under exclusive license to Springer Nature Ltd. Chemistry.

图4. (a)超分子聚合物网络SPN-DTG和MSPNs的组装及其刺激响应; (b)凝胶剂TAPA的分子结构

Figure 4. (a) Assembly of supramolecular polymer networks SPN-DTG and MSPNs and their stimulus responses; (b) Molecular structure of gel TAPA (a) Reprinted with permission from Ref. [27], Copyright 2021, American Chemical Society; (b) Reprinted with permission from Ref. [28], Copyright 2021, Elsevier Inc.

图5. (a) BP4VA和TMGE共组装构建具有酸刺激响应的CPL体系BP4VA-TMGE; (b) TA和TPEs通过非共价共聚制备超分子聚合物胶体材料; (c)聚(TA-A)8/1制备的标签在不同条件下的发光和防伪应用

Figure 5. (a) BP4VA and TMGE assembly to construct BP4Va-TMGE of CPL system with acid stimulation response; (b) Preparation of supramolecular polymer colloid materials by non-covalent copolymerization of TA and TPEs; (c) Luminescence and anti-counterfeiting applications of poly (TA-A)8/1 under different conditions (a) Reprinted with permission from Ref. [29], Copyright 2021, American Chemical Society; (b) and (c) Reprinted with permission from Ref. [30], Copyright 2022, The Royal Society of Chemistry.

图6. (a)室温自愈超分子聚氨酯(PU)PUHD-NAGA和PUIP-NAGA的合成步骤; (b)双对吡啶苯甲酰腙在不同环境下的超分子聚合途径; (c)单体M1的化学结构和其超分子聚合过程, 以及随着M1浓度的增加荧光颜色变化

Figure 6. (a) Procedure for the synthesis of room temperature self-healing supramolecular polyurethane (PU)PUHD-NAGA and PUIP-NAGA; (b) Supramolecular polymerization pathway of bispyridine-benzoylhydrazone in different environments; (c) Chemical structures of monomer M1 and its supramolecular polymerization process and the change of fluorescence color with the increase of M1 concentration (a) Reprinted with permission from Ref. [31], Copyright 2020, WILEY-VCH GmbH; (b) Reprinted with permission from Ref. [32], Copyright 2022, WILEY-VCH GmbH; (c) Reprinted with permission from Ref. [33], Copyright 2022, WILEY-VCH GmbH.

图7. (a)手性掺杂剂(R-/S-Guest 1)、P-1 (Guest 2)和M-N*-LCs和P-N*-LCs的构成原理图; (b) NCSNs、肝素、硫酸软骨素-4和透明质酸的化学结构, 以及由氰二苯乙烯基超分子聚合物结合的多价肝素

Figure 7. (a) Structural formulas for chiral dopants (R-/S-Guest 1), P-1 (Guest 2) and M-N*-LCs, P-N*-LCs; (b) Chemical structures of NCSNs, heparin, chondroitin sulfate-4 and hyaluronic acid, and schematic diagram of polyvalent heparin bound by cyanostilbenyl supramolecular polymer (a) Reprinted with permission from Ref. [34], Copyright 2021, WILEY-VCH GmbH; (b) Reprinted with permission from Ref. [35], Copyright 2020, The Royal Society of Chemistry.

图8. (a) L1和L2的合成以及在THF/H2O混合溶剂中自组装; (b) CBBHA-4、CBBHA-8和CBBHA-12的分子结构及凝胶的光学和荧光显微镜图像

Figure 8. (a) Synthesis of L1 and L2 and self-assembly in THF/H2O mixtures; (b) Molecular structures of CBBHA-4, CBBHA-8 and CBBHA-12, and optical microscope and fluorescence microscope images of CBBHA-8 1,2-DCE gel (a) Reprinted with permission from Ref. [36], Copyright 2022, The Royal Society of Chemistry; (b) Reprinted with permission from Ref. [37], Copyright 2020, The Royal Society of Chemistry.

图9. (a) HT-G和CN–识别机制的形成; (b) 2,2'-双苯并咪唑衍生物(BC6)的合成路线BC6在DMSO-H2O中的SEM图像及Tyndall效应照片; (c) AD和CZIPA通过自组装形成共晶材料

Figure 9. (a) Formation schematic diagram of the HT-G and CN– recognition mechanism; (b) Synthesis route of 2,2'-dibenzimidazole derivative (BC6) SEM image of BC6 in DMSO-H2O and Tyndall effect photo; (c) AD and CZIPA form eutectic materials through self-assembly (a) Reprinted with permission from Ref. [38], Copyright 2021, Elsevier Inc.; (b) Reprinted with permission from Ref. [39], Copyright 2022, Elsevier Inc.; (c) Reprinted with permission from Ref. [40], Copyright 2023, Elsevier Inc.

图10. (a) TNQ的结构和提出的连续监测PA的识别机制; (b) 化合物的结构式和晶体状态下的分子堆叠

Figure 10. (a) Structure of TNQ and the proposed recognition mechanism for continuous monitoring of PA; (b) Structural formula for compound, and molecular stack in the crystal state (a) Reprinted with permission from Ref. [41], Copyright 2020, Elsevier Inc.; (b) Reprinted with permission from Ref. [42], Copyright 2021, The Royal Society of Chemistry.

图11. (a) A12-TPE和T12-TPE的结构; (b) TPE-Octa-dU和TPE-EdU的结构式

Figure 11. (a) Structures of A12-TPE and T12-TPE; (b) Structural formulas of TPE-Octa-dU and TPE-EdU (a) Reprinted with permission from Ref. [43], Copyright 2021, Elsevier Inc.; (b) Reprinted with permission from Ref. [44], Copyright 2021, Elsevier Inc.

图12. (a) CB[7]?TPPE的形成原理及水溶液中对甲基苯丙胺的检测机理; (b) CBs/HA-BrBP超分子伪紫杉烷聚合物在水溶液中的结构和细胞染色; (c) CB[8]和1~5的化学结构以及不同自组装结构

Figure 12. (a) Formation principle of CB[7]?TPPE and the detection mechanism of methamphetamine in aqueous solution; (b) Structure and cell staining of the CBs/HA-BrBP supramolecular pseudo-taxane polymer in aqueous solution; (c) Chemical structures of CB[8] and 1~5, and different self-assembled structures (a) Reprinted with permission from Ref. [46], Copyright 2021, Elsevier Inc.; (b) Reprinted with permission from Ref. [47], Copyright 2020, The Authors, under exclusive license to Springer Nature Ltd.; (c) Reprinted with permission from Ref. [48], Copyright 2020, WILEY-VCH GmbH.

图13. (a)客体分子T1、P1和主体分子CB[n]的化学结构, 以及T1-CB[n]、P1-CB[n]超分子组装结构和荧光增强还原的形成; (b)近红外发射超分子纳米颗粒的形成

Figure 13. (a) Chemical structures of guest molecules T1, P1 and host molecules CB[n], and supramolecular assembly structures of T1-CB[n] and P1-CB[n] and formation of fluorescence enhanced reduction; (b) Formation of near infrared emission supramolecular nanoparticles (a) Reprinted with permission from Ref. [49], Copyright 2021, Elsevier Inc.; (b) Reprinted with permission from Ref. [50], Copyright 2021, WILEY-VCH GmbH.

图14. (a)纯有机光收集PET系统的超分子组装及其相关分子的构建及其在生物成像领域的应用; (b)在有无AIEgens的情况下CB[8]和NaBr组装成微柱

Figure 14. (a) Supramolecular assembly of pure organic light collection PET system and construction of related molecules and their applications in the field of biological imaging; (b) CB[8] and NaBr assemble into microcolumns in the presence or absence of AIEgens (a) Reprinted with permission from Ref. [51], Copyright 2021, The Royal Society of Chemistry; (b) Reprinted with permission from Ref. [52], Copyright 2021 ChemRxiv.

图15. (a) PPTA-CB[7]的自组装机理图及其能量传递过程; (b)基于NPyP-CB[8]的光收集系统

Figure 15. (a) Self-assembly mechanism of PPTA-CB[7] and its energy transfer process; (b) Light collection system based on NPyP- CB[8] (a) Reprinted with permission from Ref. [53], Copyright 2022, Elsevier Inc.; (b) Reprinted with permission from Ref. [54], Copyright 2023, The Royal Society of Chemistry.

图16. (a) Q[10]和TPE-B的化学结构; (b) CB[7]?PCS和CP?PCS溶液的可见和荧光图像; (c)系统A和B的构建

Figure 16. (a) Chemical structures of Q[10] and TPE-B; (b) Visible and fluorescent images of CB[7]?PCS and CP?PCS solutions; (c) Building system A and B (a) Reprinted with permission from Ref. [55], Copyright 2022, The Royal Society of Chemistry; (b) Reprinted with permission from Ref. [56], Copyright 2023, Elsevier Inc.; (c) Reprinted with permission from Ref. [57], Copyright 2023, Elsevier Inc.

图17. (a)双酰基腙化合物的双色荧光变化; (b) p(NIPAM-co-PgMA-CD-co-AEMA-TPE)的合成及与Ad-(DOTA-Gd)的螯合

Figure 17. (a) Dichroic fluorescence changes of diacylhydrazone compounds; (b) Synthesis of p(NIPAM-co-PgMA-CD-co-AEMA- TPE) and chelation with Ad-(DOTA-Gd) (a) Reprinted with permission from Ref. [58], Copyright 2021, The Royal Society of Chemistry; (b) Reprinted with permission from Ref. [59], Copyright 2021, WILEY-VCH GmbH

图18. (a)金属环和客体的化学结构; (b)动态轮烷枝化树状大分子PYG3

Figure 18. (a) Chemical structures of metallic rings and guest; (b) Dynamic rotane dendritic macromolecule PYG3 (a) Reprinted with permission from Ref. [60], Copyright 2022, The Royal Society of Chemistry; (b) Reprinted with permission from Ref. [61], Copyright 2022, Elsevier Inc.

图19. (a)基于可循环超分子组件G?H检测和去除水中Hg2+; (b)连续能量转移光收集系统的制备以及WP5、G、ESY和NiR的化学结构

Figure 19. (a) Cyclic supramolecular component G?H detects and decreases Hg2+ in water; (b) Preparation of a continuous energy transfer light collection system and the chemical structures of WP5, G, ESY, and NiR (a) Reprinted with permission from Ref. [62], Copyright 2021, John Wiley and Sons; (b) Reprinted with permission from Ref. [63], Copyright 2023, Elsevier Inc.

图20. (a)超分子聚合物的结构转换以及可调节聚集诱导荧光发射; (b)由H和G构成的AIE超分子聚合物; (c) SPPs的结构

Figure 20. (a) Structural transformation of supramolecular polymers and adjustable aggregation-induced fluorescence emission; (b) AIE supramolecular polymer composed of H and G; (c) Structure of SPPs (a) Reprinted with permission from Ref. [64], Copyright 2020, Elsevier Inc.; (b) Reprinted with permission from Ref. [65], Copyright 2020, Frontiers Media S.A.; (c) Reprinted with permission from Ref. [66], Copyright 2020, Elsevier Inc.

图21. (a)由H和G构成的AIE超分子高分子材料; (b)大环主体单体TPE-DBC、主链主体聚合物Poly(TPE-DBC)、客体FL-DBA和Neutralized-FL-DBA的化学结构; (c)超分子自组装主客体TPE-DBC/FL-DBA及铝离子检测机制

Figure 21. (a) AIE supramolecular polymer materials composed of H and G; (b) Chemical structures of macrocyclic host monomer TPE-DBC, main chain host polymer Poly(TPE-DBC) and guest FL-DBA and Neutralized FL-DBA; (c) Supramolecular self-assembly master-guest TPE-DBC/FL-DBA and aluminum ion detection mechanism (a) Reprinted with permission from Ref. [67], Copyright 2021, Elsevier Inc.; (b) and (c) Reprinted with permission from Ref. [68], Copyright 2021, American Chemical Society.

图22. (a)由CV衍生物和柱状[5]芳烃基聚合物主体形成的SPNs; (b) MeP5和Trp通过主客体相互作用的识别机制

Figure 22. (a) SPNs formed by CV derivatives and pillar[5]arene-based polymer hosts; (b) MeP5 and Trp identified through the mechanism of host-guest interaction (a) Reprinted with permission from Ref. [69], Copyright 2021, American Chemical Society; (b) Reprinted with permission from Ref. [70], Copyright 2021, Elsevier Inc.

图23. (a)超分子AIE化学发光单线态制氧系统; (b) i) G、M和H的化学结构和ii)用SNPs作为药物纳米载体的SNPs@DOX的制作和图像引导药物传递

Figure 23. (a) Supramolecular AIE chemiluminescence singlet oxygen production system; (b) 1) Chemical structures of G, M and H, and ii) fabrication of SNPs@DOX using SNPs as drug nanocallers and image-guided drug delivery (a) Reprinted with permission from Ref. [71], Copyright 2021, Elsevier Inc.; (b) Reprinted with permission from Ref. [72], Copyright 2021, The Royal Society of Chemistry.

图24. (a) SCD-AnEA超分子组装示意图; (b)基于柱状[5]芳烃基超分子聚合物凝胶的结构与性能; (c)基于ET途径光调制的可控光收集纳米系统

Figure 24. (a) SCD-AnEA supramolecular assembly; (b) Structure and properties of column [5] aromatic supramolecular polymer gel; (c) A controlled light collection nano-system based on ET path optical modulation (a) Reprinted with permission from Ref. [73], Copyright 2020, WILEY-VCH GmbH; (b) Reprinted with permission from Ref. [74], Copyright 2021, WILEY-VCH GmbH; (c) Reprinted with permission from Ref. [75], Copyright 2021, Elsevier Inc.

图25. (a) AIE分子及S-AIE、DSPE-PEG-AIE和CC5A-12C的化学结构; (b) TPR、α-CD-TPR和α-CD-GEM的化学结构, 及α-CD-TPRGEM-mmp(+) NPs的主客体组装和肿瘤微环靶向激活和GSH触发药物释放; (c) CD基糖团簇和超交联AIE活性纳米聚合体作为酚类荧光探针的合成路线; (d)荧光超分子硅聚合物的结构

Figure 25. (a) Chemical structures of AIE molecule and S-AIE, DSPE-PEG-AIE, CC5A-12C; (b) Chemical structures of TPR, α-CD- TPR, and α-CD-GEM, and schematic diagram of host-guest assembly of α-CD-TPRGEM-mmp(+) NPs and multiple stages of tumor microtarget activation and GSH-triggered drug release; (c) CD-based sugar clusters and hypercrosslinked AIE active nanopolymers used as synthesis routes for phenolic fluorescent probes; (d) Structure of fluorescent supramolecular silicon polymer (a) Reprinted with permission from Ref. [76], Copyright 2020, WILEY-VCH GmbH; (b) Reprinted with permission from Ref. [77], Copyright 2020, American Chemical Society; (c) Reprinted with permission from Ref. [78], Copyright 2020, The Royal Society of Chemistry; (d) Reprinted with permission from Ref. [79], Copyright 2020, The Royal Society of Chemistry.

图26. (a)主体分子H和客体分子G的结构以及超分子水凝胶的形成; (b)双吡啶基给体和双铂(II)的自组装

Figure 26. (a) Structural diagram of subject molecule H and guest molecule G, and formation of supramolecular hydrogels; (b) Self-assembly of dipyridinyl donor and diplatinum(II) (a) Reprinted with permission from Ref. [80], Copyright 2020, The Royal Society of Chemistry; (b) Reprinted with permission from Ref. [81], Copyright 2021, The Royal Society of Chemistry.

图27. (a) OU的结构及其凝胶的自组装过程以及OUG离子传感过程; (b) BTG的形成及其刺激响应; (c) MTP5?HB的形成及离子检测机制

Figure 27. (a) Structure of OU and the self-assembly process of its gels, and the schematic diagram of the OUG ion sensing process; (b) BTG formation and its stimulus response; (c) MTP5?HB forming principle of HB figure and ion detection mechanism (a) Reprinted with permission from Ref. [82], Copyright 2020, The Royal Society of Chemistry; (b) Reprinted with permission from Ref. [83], Copyright 2021, Elsevier Inc.; (c) Reprinted with permission from Ref. [84], Copyright 2020, Elsevier Inc.

图28. (a) TPEE4+, TP2–, BPy2–, BPh2–, TPh2–的离子结构式以及所形成的各种氨基和羧基之间的氢键; (b) LS/PEO114-b-PDMA- EMA24 PICs荧光组件

Figure 28. (a) Ionic structural formulas of TPEE4+, TP2–, BPy2–, BPh2–, TPh2–, and the hydrogen bonds formed between various amino and carboxyl groups; (b) LS/PEO114-b-PDMAEMA24 PICs fluorescent component (a) Reprinted with permission from Ref. [85], Copyright 2021, WILEY-VCH GmbH; (b) Reprinted with permission from Ref. [86], Copyright 2021, Elsevier Inc.

图29. (a)基于水超分子肽纳米管的人工捕光系统; (b)多色荧光聚合物水凝胶的材料设计原理以及开发的具有自适应变色行为的仿生软皮肤

Figure 29. (a) Artificial light trapping system based on water supramolecular peptide nanotubes; (b) Material design schematic of multi-color fluorescent polymer hydrogels and development of bionic soft skin with adaptive color-changing behavior (a) Reprinted with permission from Ref. [87], Copyright 2021, American Chemical Society; (b) Reprinted with permission from Ref. [88], Copyright 2022, WILEY-VCH GmbH.

图30. (a) OEGs在TPEs水溶液中的溶剂化调节超分子手性组装; (b)通过对映选择性共组装的双螺旋π聚合; (c)金属骨架的合成路线、预聚体、聚合物网络的形成

Figure 30. (a) Supramolecular chiral assembly regulated by solvation of OEGs in TPEs aqueous solutions; (b) Double helix π polymerization by enantioselective co-assembly; (c) Synthetic route of metal skeleton, prepolymer and polymer networks (a) Reprinted with permission from Ref. [89], Copyright 2021, American Chemical Society; (b) Reprinted with permission from Ref. [90], Copyright 2022, The Authors, under exclusive license to Springer Nature Ltd.; (c) Reprinted with permission from Ref. [91], Copyright 2022, WILEY-VCH GmbH.

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