Progress in Design and Application of Supramolecular Fluorescent Systems Based on Difluoroboron-Dipyrromethene and Macrocyclic Compounds

doi:10.6023/cjoc202103012

Abstract

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

Cite this article

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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Fig. & Tab. 24

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Scheme 8. Photoresponsive, water-soluble supramolecular dendronized polymer

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

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