Intramolecular interactions of a phenyl/perfluorophenyl pair in the formation of supramolecular nanofibers and hydrogels

Shu Min Hsu, Yu Chun Lin, Jui Wen Chang, Yu Hao Liu, Hsin-Chieh Lin*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

56 Scopus citations

Abstract

A new system for the incorporation of a phenyl/perfluorophenyl pair in the structure of a peptide hydrogelator was developed. The strategy is based on the idea that the integration of an end-capped perfluorophenyl group and a phenylalanine with a phenyl moiety in the side chain forms an intramolecular phenyl/perfluorophenyl pair, which can be used to promote the formation of the supramolecular nanofibers and hydrogels. This work illustrates the importance of structure-hydrogelation relationship and provides new insights into the design of self-assembly nanobiomaterials. Intramolecular binding: The incorporation of a phenyl/perfluorophenyl pair into the structure of a peptide hydrogelator leads to the formation of the supramolecular nanofibers. The quadrupole-dipole- quadrupole (q-d-q) interactions between the aromatic rings facilitate self-assembly. This work illustrates the importance of the structure- hydrogelation relationship and provides new insights into the design of self-assembled nanobiomaterials.

Original languageEnglish
Pages (from-to)1921-1927
Number of pages7
JournalAngewandte Chemie - International Edition
Volume53
Issue number7
DOIs
StatePublished - 10 Feb 2014

Keywords

  • hydrogels
  • nanofibers
  • noncovalent interactions
  • self-assembly
  • supramolecular chemistry

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