基于大环化合物与二氟硼二吡咯亚甲基的超分子荧光系统的设计及应用研究进展

doi:10.6023/cjoc202103012

摘要/Abstract

大环化合物由于其独特的刚性结构, 功能性和主客体特性在超分子化学中起着至关重要的作用, 除了常见的环糊精、杯芳烃、杯吡咯、葫芦脲和柱芳烃之外, 近些年来还出现了很多新型大环分子. 二氟硼二吡咯亚甲基(BODIPY)染料因其优异的光学性质, 包括吸收和荧光发射带窄、摩尔吸收系数和量子产率高以及良好的光、热以及化学稳定性, 被广泛应用于生物与化学领域. 大环化合物的官能团化已被证明是构建具有特定功能智能材料的有效策略之一. 该综述根据BODIPY与大环化合物所构建的超分子系统的功能应用, 对近年来报道的这类超分子系统进行了分类总结和讨论, 并提出了该领域未来的发展方向.

关键词: 杯芳烃, 杯吡咯, 环糊精, 葫芦脲, 柱芳烃, 二氟硼二吡咯亚甲基(BODIPY), 超分子化学

Macrocyclic compounds play an important role in supramolecular chemistry because of their unique shape, reactivity and host-guest properties. Cyclodextrin, calixarene, calixpyrrole, cucurbituril and pillararene are the most common macrocyclic compounds. In addition, many new macrocyclic molecules have been reported in recent years. Difluoroboron- dipyrromethene (BODIPY) dyes are widely used in biological and chemical fields because of their excellent optical properties, including narrow absorption and fluorescence emission bands, high molar absorption coefficient, high quantum yield and good light, thermal and chemical stability. The combination of macrocyclic compounds and BODIPY dyes has been proved to be an effective strategy for the construction of smart materials with specific properties. In this review the macrocyclic compounds containing BODIPY reported in recent years have been summarized and discussed based on the functional application, and the future development direction in this field is put forward.

Key words: calixarene, calixpyrrole, cyclodextrin, cucurbituril, pillararene, difluoroborondipyrromethene (BODIPY), supramolecular chemistry

引用此文

郭京京, 郭敏捷. 基于大环化合物与二氟硼二吡咯亚甲基的超分子荧光系统的设计及应用研究进展[J]. 有机化学, 2021, 41(8): 2946-2963.

Jingjing Guo, Minjie Guo. Progress in Design and Application of Supramolecular Fluorescent Systems Based on Difluoroboron-Dipyrromethene and Macrocyclic Compounds[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 2946-2963.

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图/表 24

图1. 大环化合物的化学结构: (a)环糊精, (b)杯芳烃, (c)杯吡咯, (d)葫芦脲, (e)柱芳烃, (f)联苯芳烃, (g)萘基杯芳烃、(h)塔芳烃, (i)环带芳烃, (j)螺芳烃, (k)领结芳烃

Figure 1. Chemical structures of macrocyclic compounds: (a) cyclodextrin, (b) calixarene, (c) calixpyrrole, (d) cucurbituril, (e) pillararene, (f) biphenarene, (g) naphthyl calixarene, (h) pagodaarene, (i) cycloparaphenylene, (j) helicarene, and (k) bowtiearene

图2. BODIPY母核结构(a)及荧光调节机理: FRET (b), PET (c), ICT (d)

Figure 2. BODIPY core structure (a) and fluorescence regulation mechanism: FRET (b), PET (c), ICT (d)

图3. 用于pH值检测的BODIPY修饰的杯[4]芳烃1

Figure 3. BODIPY-functionalized calix[4]arene 1 for pH detection

图式1. 用于Ca2+检测的BODIPY修饰的杯[4]芳烃2

Scheme 1. BODIPY-functionalized calix[4]arene 2 for Ca2+detection

图4. 用于Ca2+检测的BODIPY修饰的杯[4]芳烃3~5的化学结构

Figure 4. Chemical structures of BODIPY-functionalized calix[4]arene 3~5 for Ca2+ detection

图式2. 在生理条件下检测K+的BODIPY修饰的杯[4]芳烃6

Scheme 2. BODIPY-functionalized calix[4]arene 6 for K+ detection under physiological conditions

图5. 用于Cs+离子检测的BODIPY修饰的杯[4]芳烃

Figure 5. BODIPY-functionalized calix[4]arene for Cs+ detection

图式3. 用于Cu2+检测的BODIPY修饰的硫杂杯[4]芳烃

Scheme 3. BODIPY-functionalized thiacalix[4]arene for Cu2+detection

图式4. 用于Yb3+检测的BODIPY修饰的杯[4]芳烃

Scheme 4. BODIPY-functionalized calix[4]arene for Yb3+ detection

图式5. 用于检测Hg2+的BODIPY修饰的杯[4]芳烃

Scheme 5. BODIPY-functionalized calix[4]arene for Hg2+ detection

图式6. 检测L-天门冬酰胺的BODIPY修饰的柱[5]芳烃12

Scheme 6. BODIPY-functionalized pillar[5]arene 12 for L-Asn detection

图6. 用于阴离子检测的双杯[4]吡咯修饰的BODIPY 13及其母体BODIPY单元14

Figure 6. Bis(calix[4]pyrrole)-functionalized BODIPY 13 for anions detection and its parent BODIPY unit 14

图7. 用于阴离子检测的单杯[4]吡咯修饰的BODIPY 15及吡咯修饰的BODIPY 16

Figure 7. Monocalix[4]pyrrole-functionalized BODIPY 15 for anions detection and its reference compound 16

图8. 用于阴离子检测的双杯[4]吡咯修饰的BODIPY 17、单杯[4]吡咯修饰的BODIPY化合物18、二羧酸阴离子C0, C3, C5~C10, N1~N3以及环状复合物17?C8

Figure 8. Bis(calix[4]pyrrole)-functionalized BODIPY 17 for anions detection, monocalix[4]pyrrole functionalized BODIPY 18, dicarboxylate anions C0, C3, C5~C10 and N1~N3, and Cyclic complex17?C8

图9. 用于F–检测的杯[4]吡咯修饰的BODIPY 19

Figure 9. Calix[4]pyrrole functionalized BODIPY 19 for F– detection

图10. 基于BODIPY和杯[4]芳烃的光敏剂的化学结构

Figure 10. Structure of the photosensitizer based on BODIPY and calix[4]arene

图11. 构建化学-光动力双重疗法的超分子体系的H1, DOX, G1的化学结构

Figure 11. Chemical structures of H1, DOX, G1 of the supramolecular system for chemo-photodynamic dual therapy

图12. H2, G2, G3的化学结构(a)及基于它们构建的用来模拟光捕获系统的超分子体系(b)

Figure 12. Chemical structures of H1, G2, G3 (a) and the supramolecular system based on them for mimicking the light-harvesting system (b)

图13. 用于模拟光捕获系统的全BODIPY官能化的柱[5]芳烃的化学结构

Figure 13. Chemical structure of BODIPY perfunctionalized pillar[5]arene for mimicking the light harvesting system

图14. 构建具有高效三重态-三重态上转化湮灭能力超分子体系的主客体分子的化学结构

Figure 14. Chemical structures of host and guest molecules of supramolecular system with high-efficiency triplet-triplet annihilation upconversion (TTA-UC)

图式7. 含BODIPY的荧光[2]轮烷H3-G4及其相应的超分子凝胶的多刺激响应性行为

Scheme 7. Multistimuli sensitive behavior of BODIPY-involved fluorescent [2]rotaxane H3-G4 and its corresponding supramolecular gel

图15. 含葫芦[7]脲锚定基团的BODIPY (G5~G9)及葫芦[7]脲(H4)的化学结构

Figure 15. Chemical structure of BODIPY with cucurbit[7]uril anchor group and cucurbit[7]uril

图式8. 水溶性光响应性超分子树枝状聚合物

Scheme 8. Photoresponsive, water-soluble supramolecular dendronized polymer

图16. 构建形态可变的主链超分子聚合物两亲体的分子的化学结构

Figure 16. Chemical structure of molecules of main chain supramolecular polymer amphiphiles with variable morphology

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