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Supramolecular chemistry combines the strength of molecular assembly via various molecular interactions. Hydrogen bonding facilitated self-assembly with the advantages of directionality, specificity, reversibility, and strength is a promising approach for constructing advanced supramolecules. There are still some challenges in hydrogen bonding based supramolecular polymers, such as complexity originating from tautomerism of the molecular building modules, the assembly process, and structure versatility of building blocks. In this review, examples are selected to give insights into multiple hydrogen bonding driven emerging supramolecular architectures. We focus on chiral supramolecular assemblies, multiple hydrogen bonding modules as stimuli responsive sources, interpenetrating polymer networks, multiple hydrogen bonding assisted organic frameworks, supramolecular adhesives, energy dissipators, and quantitative analysis of nano-adhesion. The applications in biomedical materials are focused with detailed examples including drug design evolution for myotonic dystrophy, molecular assembly for advanced drug delivery, an indicator displacement strategy for DNA detection, tissue engineering, and self-assembly complexes as gene delivery vectors for gene transfection. In addition, insights into the current challenges and future perspectives of this field to propel the development of multiple hydrogen bonding facilitated supramolecular materials are proposed. [ABSTRACT FROM AUTHOR]

In this paper, two types of solid phase 2D and 3D XBOFs were selectively constructed from identical building blocks of tetraphenylmethane tetrapyridine derivative and 1,4-diiodotetrafluorobenzene by changing the crystallization solvent. This 3D XBOF is a novel hybrid supramolecular organic framework with the synergistic control of hydrogen and halogen bonds. [ABSTRACT FROM AUTHOR]

A series of peptide-appended bisresorcinarenes were synthesized, which adopted tubular conformation induced by intramolecular hydrogen bonds. The derivatives formed unimolecular artificial transmembrane channels in lipid bilayers to enable selective transport of monovalent cations. Importantly, the channels exhibited reversible ligand-gating behavior in response to alkyl amine and Cu2+. [ABSTRACT FROM AUTHOR]

Inspired by arylamide-based oligomeric foldermers that are stabilized by intramolecular hydrogen bonding, a series of polyamides with intramolecular hydrogen-bonding motifs were synthesized viapolycondensation reactions. These polymers can fold into helical conformation different from their linear control. The chirality of helical conformation can further be tuned viaacid–base complexation using chiral residues. [ABSTRACT FROM AUTHOR]

Two hydrogen-bonded 3-mer arylamide foldamers 1 and 2, which bear two pyridine or iodobenzene subunits at the ends, have been designed and prepared. Compound 1 co-assembles with 1,4-diiodotetrafluorobenzene (3) to form 2 + 2 macrocycles through four (py)N…I halogen bonds, whereas compound 2 dimerizes into a macrocycle through two C=O…I hydrogen bonds. Macrocycles formed by 1 and 3 stack to produce a supramolecular tube, with two neighboring macrocycles encapsulating one molecule of 3 through two C=O…I halogen bonds. Through such a cross-layer connection, formally the two molecules also give rise to a new halogen-bonded supramolecular helix, and further stack alternately to afford a double helix. In contrast, the mixture of 1 and fumaric acid (5) did not produce a similar encapsulation-derived helix, even though they also formed a halogen-bonded 2 + 2 supramolecular macrocycle. [ABSTRACT FROM AUTHOR]

A hydrogen bonded foldamer unit and an azobenzene unit have been incorporated into the linear component of a tristable [2]rotaxane to give rise to a doubly gated switching system tuned by the folding–defolding of the foldamer unit and the photo-initiated trans–cis isomerization of the azobenzene unit. [ABSTRACT FROM AUTHOR]