Porous 3-D honeycomb architecture by self-assembly of helical H-bonded molecular tapes

Abstract

Enantiopure dipeptide-derived 1,3,5-triazepan-2,6-diones and form H-bonded 3(1) helical molecular tapes with P chirality in the solid state; in the case of , these columnar tapes self-assemble through aromatic-aromatic interactions to give hollow tubular structures.

Synthetic Methods for the Preparation of Triazepandiones and Review of their Applications

“…Crystal structures have been reported for compounds 118a,m [46], 118c [47], 118h [48], 118k,l,n,p,r, 120a,i, 121a and 122c [43]. Supramolecular organization of compounds 118a and 118m showed a remarkable formation of helical H-bonded molecular tapes that Scheme 23.…”

“…Solution phase synthesis of 1,3,5-triazepan-2,6-diones via a succinimidyl carbamate. self assemble into a 3D-honeycomb architecture for 118a [46].…”

1,3,5‐Triazepan‐2,6‐diones as Structurally Diverse and Conformationally Constrained Dipeptide Mimetics: Identification of Malaria Liver Stage Inhibitors from a Small Pilot Library

“…The quasi-equatorial position of the side chains on C a carbons is common to both scaffolds. [40] In 1996 Lenman et al reported the design and synthesis of cis-peptidyl prolinamide mimetics based on a 4,5-fused 1,2,5-triazepane-3,6-dione skeleton that differ from the original cis-proline peptide by only two hydrogens.…”

5-(3,4-Dimethoxybenzyl)-7-isopropyl-1,3,5-triazepane-2,6-dione acetonitrile solvate refined using a multipolar atom model

“…Interestingly, the nature and the number of substitutents on the ring can dramatically affect the overall geometry, with the side chain at C7 adopting a pseudo-equatorial or pseudo-axial orientation. Moreover, 1,3,5-triazepane-2,6-diones can be used in crystal engineering to create helical molecular tapes that can self-assemble to form channel-type structures (Schaffner et al, 2006). We report here the structure of the title compound, (I), an analogue of cyclo(l-Val-gSar-CO) (Aubert et al, 2007) in which the methyl group at N3 is replaced by the much bulkier 3,4-dimethoxybenzyl group.…”