Water gelation by small organic molecules.

In this review, we describe the recent advances in supramolecular helical assemblies formed from chiral and achiral small molecules, oligomers (foldamers), and helical and nonhelical polymers from the viewpoints of their formations with unique chiral phenomena, such as amplification of chirality during the dynamic helically assembled processes, properties, and specific functionalities, some of which have not been observed in or achieved by biological systems. In addition, a brief historical overview of the helical assemblies of small molecules and remarkable progress in the synthesis of single-stranded and multistranded helical foldamers and polymers, their properties, structures, and functions, mainly since 2009, will also be described.

Supramolecular Helical Systems: Helical Assemblies of Small Molecules, Foldamers, and Polymers with Chiral Amplification and Their Functions

Chirality seems to be intimately associated with the growth and stability of self-assembled fibrillar networks and with the most common macroscopic property of these networks, which is the thermoreversible gelation of the solvent. The presence and the relative configurations of stereogenic centers in the structure of a small molecule gelator are generally (but not always) observed to be critical to its ability to form gels. Symmetry considerations of chiral molecular packing provide thermodynamic and kinetic arguments that may explain why chirality favors fiber growth. Additionally, molecular chirality is sometimes expressed at a scale of nanometers or micrometers and gives rise to twisted or coiled fiber structures that are readily observable by microscopic techniques. These chiral fiber morphologies have already found some applications as templates for helical protein crystallization or for the growth of chiral inorganic replicas. The chiroptical properties of assembled chiral molecules, e.g., circular dichroism, allow monitoring of aggregation and may sometimes give insights into molecular packing. But determining chiral molecular arrangements in the fibers remains a challenge and requires the use of multiple techniques.

Chirality Effects in Self-assembled Fibrillar Networks.

Carbohydrates are involved in a variety of biological processes. The ability of sugars to form a large number of hydrogen bonds has made them important components for supramolecular chemistry. We discuss recent advances in the use of carbohydrates in supramolecular chemistry and reveal that carbohydrates are useful building blocks for the stabilization of complex architectures. Systems are presented according to the scaffold that supports the glyco-conjugate: organic macrocycles, dendrimers, nanomaterials, and polymers are considered. Glyco-conjugates can form host–guest complexes, and can self-assemble by using carbohydrate–carbohydrate interactions and other weak interactions such as π–π interactions. Finally, complex supramolecular architectures based on carbohydrate–protein interactions are discussed.

Carbohydrates in Supramolecular Chemistry

Nanotubes Self-Assembled from Amphiphilic Molecules via Helical Intermediates

The first self-organized quadruple helices consisting of monopolymeric material have been obtained from N-octyl- and N-dodecyl-D-gluconamides in water. The have been characterized by electron microscopy, image analysis, and computer modelling. The pitch of helices is equal to (2π×molecular bilayer diameter); their gradient conforms with the magic angle (54.7 o ). The quadruple helices rearrange in aqueous gels to a single helix made of circular 4-fold layers of molecules, a pitch of 7.4 nm, and a gradient of 82±3 o

Magic angle (54.7.degree.) gradient and minimal surfaces in quadruple micellar helices

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Magic angle (54.7.degree.) gradient and minimal surfaces in quadruple micellar helices