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

Chem Commun (Camb). 2019 Jul 18;55(59):8548-8551. doi: 10.1039/c9cc03906f.

Abstract

Benzene-1,3,5-tricarboxamide monomers derived from alkyl esters of tryptophan (BTA Trp) self-assemble into helices with an inner threefold hydrogen bond network surrounded by a second network involving the indole N-H groups. As a consequence of this extra stabilization of its helical assemblies, BTA Trp forms more viscous solutions than a range of ester and alkyl BTAs.