Chiral and non-chiral assemblies from lipidated serine-based pseudopeptidic moleculesElectronic supplementary information (ESI) available: Experimental details, NMR, mass spectra, and microscopy images. See DOI: 10.1039/c6me00009f

• Main Authors: Bijesh, M. B, Dheepthi, N. U, Sapala, Appa Rao, Shandilya, Ashutosh, Khare, Kedar, Haridas, V
• Format: Journal Article
• Published: 02.08.2016
• DOI: 10.1039/c6me00009f

A series of lipidated molecules l -A1- l -A5 containing two serine units linked by a variety of aromatic spacers were designed and synthesized. Compound l -A1 containing a m -xylylene unit self-assembled into intertwined twisted-ribbons, while compound l -A2 containing a p -xylylene unit formed nano-sized twisted-ribbons. A racemic mixture of l -A1 and d -A1 showed tapes, while a racemate from l -A2 and d -A2 showed fibres. In contrast, compounds l -A3 and l -A4 containing a benzene-1,3-dicarbonyl spacer showed a fibrillar morphology. Control over self-assembly was achieved by the choice of aromatic spacers and N-terminal substituents. The need for molecular curvature for the formation of twisted ribbons was demonstrated by the inability of control compound l -A5 to form twisted-ribbons. Through various examples, we demonstrated serine as an excellent building block for the design of chiral and non-chiral self-assembled materials. The fine parameters such as pitch, angle and helicity can be altered using clever molecular engineering.