A terminally protected dipeptide: from crystal structure and self-assembly, through co-assembly with carbon-based materials, to a ternary catalyst for reduction chemistry in water

Daniela Mazzier, Francesco Carraro, Marco Crisma, Marzio Rancan, Claudio Toniolo, Alessandro Moretto*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

A terminally protected, hydrophobic dipeptide Boc-l-Cys(Me)-l-Leu-OMe (1) was synthesized and its 3D-structure was determined by single crystal X-ray diffraction analysis. This peptide is able to hierarchically self-assemble in a variety of superstructures, including hollow rods, ranging from the nano- to the macroscale, and organogels. In addition, 1 is able to drive fullerene (C60) or multiwalled carbon nanotubes (MWCNTs) in an organogel by co-assembling with them. A hybrid 1-C60-MWCNT organogel was prepared and converted (through a high vacuum-drying process) into a robust, high-volume, water insoluble, solid material where C60 is well dispersed over the entire superstructure. This ternary material was successfully tested as a catalyst for: (i) the reduction reaction of water-soluble azo compounds mediated by NaBH4 and UV-light with an overall performance remarkably better than that provided by C60 alone, and (ii) the NaBH4-mediated reduction of benzoic acid to benzyl alcohol. Our results suggest that the self-assembly properties of 1 might be related to the occurrence in its single crystal structure of a sixfold screw axis, a feature shared by most of the linear peptides known so far to give rise to nanotubes.

Original languageEnglish
Pages (from-to)238-245
Number of pages8
JournalSoft Matter
Volume12
Issue number1
DOIs
Publication statusPublished - 7 Oct 2015
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)
  • Condensed Matter Physics

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