Improved functionality and control in the isomerization of a calix[4]arene-capped azobenzene

Paul A. Bonvallet, Max R. Mullen, Paul J. Evans, Kristen L. Stoltz, Erica N. Story

Research output: Contribution to journalArticlepeer-review

15 Scopus citations


An improved azobenzene core capped by two calix[4]arene units isomerizes readily between trans and cis configurations via photochemical and/or thermal means. In addition, the presence of acid (particularly HCl) increases the rate of thermal cis→trans conversion. These enhancements to the functional response, control, and understanding of calixarene-capped azobenzene isomerization are important for future application in the dynamic encapsulation of small chemical species.

Original languageEnglish (US)
Pages (from-to)1117-1120
Number of pages4
JournalTetrahedron Letters
Issue number10
StatePublished - Mar 9 2011

Bibliographical note

Funding Information:
This work was funded by the College of Wooster , the Copeland Fund for Independent Study , the Wilson Fund , and NSF Grants CHE-9977546 and CHE-0704026 . We thank the Mass Spectrometry Center of the University of Akron and the Department of Macromolecular Science and Engineering at Case Western Reserve University ( NSF Grant CHE-0821515 ) for instrumental support.


  • Azobenzene
  • Calixarene
  • Photoisomerization
  • Stimuli-responsive material
  • Thermal isomerization


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