Self-assembly with hydrogen bonding

Corbin, P. S. Lawless, L. J. Li, Z. Ma, Y Winner, M. J. Zimmerman, S. C. Discrete and polymeric self-assembled dendrimers Hydrogen bond-mediated assembly with high stability and high fidelity. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5099-5104. 

Figure 6.7 Illustration of multipoint hydrogen bonding based self-assembly (a) hydrogen bond formation between barbituric acid functionalized gold nanoparticles and Hamilton receptor functionalized block copolymers and (b) selective deposition of nanoparticles on a microphase-separated block copolymer film. Reprinted with permission fi om Binder et al. (2005). Copyright 2005 American Chemical Society.

The pseudorotaxane self-assembles through hydrogen bonding, and the binding constant, calculated using steady-state fluorescence, is 1.4 x 10. The zinc phthalocyanine derivative exhibited an excited-state lifetime of approximately 3.1 ns. The fast decay of the excited state of 1 ZnPc upon complexation with the fullerene... 

Fig. 12 Neat melamine Hekates 40, their 1 1 host-guest complexes 41,42 and the 1 3 aggregates of a melamine core with three arms 43 and 44. The disk-shaped aggregates 41 stack in a Colrd phase [99]. The Janus-type Hekate 42 arrange in a Colh phase with hexagonal superstructure of the nanosegregated semi-perfluorinated chains [105]. The supramolecular Hekate discs 43-45 self-assemble by hydrogen bonding of the three arms around a melamine core...

Self-assembly by hydrogen bonding interactions is a very usual feature (together with the electron donor/acceptor interactions) in natural and unnatural non-covalent assembly of molecules18. 

Per-amino-CyDs form various self-assemblies by hydrogen bonding in water [159-161]. Cationic amphiphilic j8-CyDs 41, 42, substituted with hydrophobic n-alkylthio chains at the primary hydroxyl side and hydrophilic co-amino-oligo-(ethylene glycol) units at the secondary side, formed bilayer vesicles with a diameter of 30-35 nm (when alkyl = hexadecyl) or nanoparticles with a diameter of ca. 120 nm (when alkyl = hexyl) in water [159]. Sulfated amphiphilic CyDs 43-45... 

Fig. 5.7 Supramolecular chiral columnar and cubic liquid crystals formed by self-assembly of hydrogen bonded chiral disklike complex 38 with ionic stimuli. Reproduced from Ref. [53] by...

Later, Wheeler and coworkers demonstrated that chiral sulfonamidecinnamic acids self-assemble into hydrogen-bonded dimers wherein the olefins lie parallel, with the C=C bonds separated by 3.68 The approach was expanded to cross-photoreactions that generate heterodimers. On UV irradiation, the quasiracemate cocrystals underwent asymmetric photodimerizations to afford an enantiomerically pure a-truxillic acid photoproduct (Figure 21). 

Dory and co-workers synthesized a tripeptide composed of a, -unsaturated (5-amino acids (Fig. 8.10a) [45]. The trans geometry of the vinyl group was used to induce the peptide to adopt a flat conformation required for the self-assembling process. In a similar way to the nanombes from y5-peptides, the peptide backbone has an even number of atoms between the carbonyl and amino groups of each residue. As a result, all the hydrogen bonds were parallel in the nanotube (Fig. 8.10b). The same group further extended this pattern to di-, tri-, and tetrapeptides of -amino acids with a trans yS,(5-double bond (Fig. 8.10c). AU of these cyclic peptides were found to self-assemble into hydrogen bonded nanotubes [46]. 

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