Cyclobutane-based peptides/terpyridine conjugates: Their use in metal catalysis and as functional organogelators

Oriol Porcar-Tost, Bernat Pi-Boleda, Jordi García-Anton, Ona Illa, Rosa M. Ortuño

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2 Citations (Scopus)

Abstract

© 2018 Elsevier Ltd Two new conjugates, hcptpyDP and hcptpyTP, of a terpyridine derivative incorporating artificial peptide moieties, have been synthesized and their use in the preparation of metal catalysts and organogelators has been investigated. Ru(II) complexes derived from these ligands showed electrochemical behavior and activity as catalysts in the epoxidation of olefins similar to that of Beller's catalyst. As organogelators, these conjugates were able to gelate a variety of solvents, from toluene to methanol, with satisfactory mgc (minimum gelation concentration) values. The presence of 4′-(4-carboxy)phenylterpyridine (hcptpy) moiety allows tuning the gelling properties and also influences the supramolecular self-assembling mode to produce chiral aggregates with respect to parent peptides DP and TP. In the case of the conjugates, π−π interactions provided by the aromatic moieties cooperate with inter-molecular hydrogen bonding between NH and CO in the amide groups. Further properties of peptide/terpyridine conjugates are under investigation in view of future applications.
Original languageEnglish
Pages (from-to)7252-7260
JournalTetrahedron
Volume74
DOIs
Publication statusPublished - 20 Dec 2018

Keywords

  • Cyclobutane-based peptides
  • Functional organogelators
  • Metal catalysis
  • Ruthenium complexes
  • Terpyridine conjugates

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