The Structural Diversity of Benzofuran Resorcinarene Leads to Enhanced Fluorescence

Tiia Riikka Tero, Kirsi Salorinne, Heli Lehtivuori, Janne A. Ihalainen, Maija Nissinen*

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review


An unexpected and previously unknown resorcinarene mono-crown with a fused benzofuran moiety in its macrocyclic core was obtained as a by-product from a bridging reaction of tetramethoxy resorcinarene with tetraethylene glycol ditosylate. The formation of the fused benzofuran moiety in the resorcinarene macrocycle resulted in a unique rigid and puckered boat conformation, as shown by XRD studies in the solid state. Modification of the macrocycle was also observed to affect the photophysical properties in solution by enhancing the fluorescence brightness compared with a conventional resorcinarene macrocycle. The fluorescent properties enabled unique detection of structural features, that is, the rigid boat conformation with the conjugated benzofuran system and the more flexible crown bridge part, in solution.

Original languageEnglish
Pages (from-to)1860-1867
Number of pages8
JournalChemistry - An Asian Journal
Issue number7
Publication statusPublished - Jul 2014


  • benzofuran
  • calixarenes
  • fluorescence
  • resorcinarenes
  • supramolecular chemistry
  • X-ray diffraction


Dive into the research topics of 'The Structural Diversity of Benzofuran Resorcinarene Leads to Enhanced Fluorescence'. Together they form a unique fingerprint.

Cite this