Supramolecular Polymers and Assemblies. Andreas Winter
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for the self‐assembly of supramolecular polymeric nanostructures. Source: Klok et al. [42], © 1999 American Chemical Society.Figure 8.14 Schematic representation of resorcin[4]arene 10 and calix[4]arene 11. Source: Baldini et al. [45], © 2011 American Chemical Society.Figure 8.15 Schematic representation of cavitands 12 and 13. The latter one was used as AB‐type monomer in a supramolecular polymerization. Source: Dalcanale and Pinalli [19], © 2015 Springer Nature.Figure 8.16 (a) Representation of the solid‐state structure of poly‐13 (perpendicular view to the polymer chains) [52]. (b) Schematic representation of the star‐shaped supramolecular polymer, derived from a template‐driven self‐assembly using a planar tetratopic guest, as core. Source: Yebeutchou et al. [52], © 2008 John Wiley and Sons.Figure 8.17 Schematic representation of the p‐tert‐butylcalix[5]arenes 14–16. Source: Pappalardo et al. [56].Figure 8.18 Schematic representation of the bis‐calix[5]arenes 17 and the alkyl‐diammonium salts 18 used for the self‐assembly into the supramolecular architectures A‐D. Source: Gattuso et al. [60], © 2008 American Chemical Society.Figure 8.19 Schematic representation of the homoditopic “bis‐container” 19 for the complexation of fullerene derivatives, such as the dumbbell‐shaped bis‐fullerene 20 and the polyacetylene 21 with fullerene side chains.Figure 8.20 Schematic representation of the formation of a supramolecular coil–rod–coil triblock copolymer. Source: Hirao et al. [67], © 2020 American Chemical Society.Figure 8.21 Schematic representation of the homoditopic AA‐type bis‐cavitand hosts (22) and BB‐type guests (23) used for supramolecular polymerization. Source: Tancini et al. [69], © 2010 John Wiley and Sons.Figure 8.22 Representation of the crystal structure of the linear supramolecular polymer obtained from the self‐assembly of 22c and MV2+ (the counterions are omitted for clarity). Source: Tancini et al. [69], © 2010 John Wiley and Sons.Figure 8.23 (a) Schematic representation of the p‐sulfonatocalix[n]arene 24 and the corresponding homoditopic hosts 25 and 26. (b) Schematic representation of the self‐assembly of 25 into a linear or net‐like polymer upon complexation of a dicationic or tetracationic guest. Source: Guo et al. [71], © 2009 John Wiley and Sons.Figure 8.24 Schematic representation of the tetracationic bis‐viologen guests 27 and their use in the self‐assembly with bis‐calixarene 26 to afford linear polymer or cyclic oligomers. Source:(a) Redrawn from Guo et al. [73,74] © 2010 Royal Society of Chemistry; (b) Redrawn from Qian et al. © 2012 John Wiley and Sons.Figure 8.25 Schematic representation of the synthesis of a ternary supramolecular polymer via a two‐step self‐assembly approach. Source: Redrawn from Qian et al. [74], © 2012 John Wiley and Sons.Figure 8.26 Schematic representation of the pH‐ and redox‐sensitive supramolecular polymer assembled from bis‐calixarene 26 and the heteroditopic guest 28. Source: Redrawn from Ma et al. [77], © 2011 Royal Society of Chemistry.Figure 8.27 Schematic representation of the multifunctional guest 29 and the chiral supramolecular polymer derived by binding of α‐CD and 26. The polymer showed a light‐driven isomerization that could be monitored by SEM imaging of the dried cast films on glass slides. Source: Sun et al. [78]. Figure reproduced with kind permission; © 2013 American Chemical Society.Figure 8.28 Schematic representation of calix[4]pyrrole (30). The four most relevant conformations (a) as well as the anion‐induced transformation from the 1,3‐alterante to the cone‐shaped conformation (b) are also shown. Source: Wu et al. [80], © 2001 The Royal Chemical Society.Figure 8.29 Schematic representation of the TTF‐functionalized calix[4]pyrroles 31, which, in their 1,3‐alternate conformation, accommodated two electron‐poor guests. The conformation of 33 could be switched reversibly by adding chloride anions. Source: Nielsen et al. [88], © 2004 American Chemical Society.Figure 8.30 Schematic representation of the dicationic calix[4]pyrrole‐based guests 32. (a) Schematic representation of the structure of the supramolecular polymer assembled from 31c and 32a; a representative SEM image visualizing the solid‐state morphology of the material is also shown. (b) Schematic representation of the supramolecular assemblies formed by the depolymerization of (31c⋅⋅⋅32a)n in the presence of TBAI (left) and TEAI (right). Source: Kim et al. [91], © 2013 American Chemical Society. Figure reproduced with kind permission; © 2013 American Chemical Society.Figure 8.31 (a) Schematic representation of the flexible, ditopic guests 33. (b) Evolution of the DP as a function of the monomer concentration in different solvents (MCH: methylcyclohexane; DCE: 1,2‐dichloroethane). Source: Bähring et al. [92], © 2014 The Royal Chemical Society.Figure 8.32 (a) Schematic representation of the complementary ditopic monomers 34 and 35, which gave a linear supramolecular polymer due to calix[4]pyrrole–carboxylate anion recognition. Source: Yuvayapan et al. [93], © 2019 The Royal Chemical SocietyFigure 8.33 Schematic representation of the PBI dye 30 that was assembled into fibers upon addition of a p‐sulfonatocalix[n]arene (24). The TEM, SEM, and AFM images (from the left to the right) of the nanostructures are also depicted. Source: Guo et al. [96]. Figure reproduced with kind permission; © 2012 The Royal Chemical Society.Figure 8.34 Schematic representation of the reversible self‐assembly of an amphiphilic molecule in the presence of a macrocyclic host. Source: García‐Rio and Basílio [101], © 2019 Elsevier.Figure 8.35 Schematic representation of the formation of a supramolecular amphiphile, as a thermoresponsive carrier for doxorubicin hydrochloride. A representative TEM image of the vesicles is also depicted. Source: Wang et al. [104]. Figure reproduced with kind permission; © 2010 Wiley‐VCH.Figure 8.36 Schematic representation of the multiple stimuli–responsive vesicles obtained from the self‐assembly of 24 (n = 4) and 39. Source: Wang et al. [105], © 2011 American Chemical Society.Figure 8.37 Schematic representation of the multistep assembly of a linear supramolecular polymer from the heterodifunctional guest 40 and two different types of hosts. The TEM images of the three types of assemblies observed in the study are also depicted. Source: Zhang et al. [106]. Figure reproduced with kind permission; © 2014 The Royal Chemical Society.Figure 8.38 Schematic representation of the self‐assembly of 41 into vesicles and, in the presence of Ag(I) ions, spherical micelles. Source: Redrawn from ref. Houmadi et al. [122], © 2007 American Chemical Society.Figure 8.39 Schematic representation of the homoditopic guest 42 that was assembled into spherical nanostructures in the presence of the sulfonated calix[4]arene 24 (a) or bis‐calix[4]arene 26 (b). Both types of nanostructures exhibited aggregation‐induced emission. Source: Redrawn from ref. Jiang et al. [107], © 2014 American Chemical Society.Figure 8.40 Schematic representation of calix[4]arene 43 as a host for the self‐assembly into supramolecular micelles with chlorin‐e6 (Ce6). The size distribution as determined by DLS measurements (a) and a TEM image of the micelles (b) are also depicted. Source: Tu et al. [111]. Figure reproduced with kind permission; © 2011 The Royal Chemical Society.Figure 8.41 Schematic representation of an enzyme‐responsive supramolecular amphiphile for drug‐delivery applications. Source: Guo et al. [113], © 2012 American Chemical Society.Figure 8.42 Schematic representation of the self‐assembly of 44 and 45 into supramolecular amphiphiles. Source: Redrawn from Kharlamov et al. [115], © 2013 American Chemical Society.Figure 8.43 Schematic representation of the self‐assembly of 46 and 47 into supramolecular nanosheets. The TEM (a) and AFM (b) images of these nanosheets are also depicted. Well‐defined nanosheets, which are 1–2 mm long and 300–500 nm wide, are observed. Source: Yi et al. [116]. Figure reproduced with kind permission; © 2012 The Royal Chemical SocietyFigure 8.44 Schematic representation of a calix[8]arene‐based polypseudorotaxane. Source: Yamagishi et al. [119], © 2001 American Chemical Society.
9 Chapter 9Figure 9.1 Schematic representation of basic cyclodextrin (CD) structures. Source: Szejtli [4]. © 1997 American Chemical Society.Figure 9.2 (a) Schematic representations of a pseudorotaxane and a rotaxane. (b) Qualitative representation of the energy scheme for the disassembly of a [2] rotaxane into its molecular components. Source: Wenz et al. [11]. © 2006 American Chemical Society.Figure 9.3 Schematic representation of the synthesis of polypseudorotaxanes