Extra hydrogen bonding interactions by peripheral indole groups stabilize benzene-1,3,5-tricarboxamide helical assemblies

Abstract

The indole groups (Ind) of these BTA monomers provide an additional hydrogen bonding interaction that enables the formation of remarkably stable supramolecular helices.

Higher-order interfiber interactions in the self-assembly of benzene-1,3,5-tricarboxamide-based peptides in water

“…BTA-based molecules are traditionally depicted as perfectly C3-symmetrical units; however, analysis of the available crystalline BTA-based molecule structure provides evidence that even the amide groups of BTA do not necessarily retain C3 symmetry in three-dimensional space (relative to the BTA ring). [48][49][50][51][52] The molecule can be distorted from flat and C3 symmetrical, which can be further enhanced by substituent flexibility; however, the hydrogen bond network between the BTA amide groups remains unperturbed.…”

From Physical Chemistry to Chemical Physics

“…The flexibility of the side-chains present in BTA Gly monomers allows a range of energetically close conformations to be accessible in the dimeric state. Such conformations have not been detected in the case of other ester BTA monomers, [57][58][59]62 highlighting the richness of the structures accessible by simple modulation of the group connected to the amide  carbon. The co-assembly of monomers of different nature constitutes the next step for the construction of intricate functional supramolecular architectures.…”

“…44 Moreover, mixing different types of BTA monomers has recently emerged as a remarkable method to control the chirality and structure of helical co-assemblies [45][46][47][48] and construct elaborate functional supramolecular materials. 37-39, 41, 49 Deriving BTA monomers by grafting -amino esters (ester BTAs, Chart 1b) [50][51][52][53][54][55][56][57][58][59][60][61][62] is an appealing strategy to modulate the nature of groups and functions attached to the amide functions. Previous studies have revealed that the nature of the self-assemblies formed by ester BTAs is strongly dependent on the nature and stereochemistry of the group (R 1 in Chart 1b) located next to the amide function as well as on experimental conditions.…”

Hierarchical self-assembly of aromatic peptide conjugates into supramolecular polymers: it takes two to tango

“…11C). 172 Small-Angle Neutron Scattering experiments revealed long and rigid one-dimensional cylinders with L > 1000 Å and DP w > 275, and circular dichroism showed intense signals that originate from the chiral nanoscale organization of the supramolecular polymers (Fig. 11D).…”