The structural diversity of benzofuran resorcinarene leads to enhanced fluorescence.
An unexpected and previously unknown resorcinarene mono-crown with a fused benzofuran moiety in its macrocyclic core was obtained as a byproduct 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.
Department of Chemistry, Nanoscience Center, University of Jyväskylä, P.O. Box 35, 40014 JYU (Finland).
Tiia-Riikka
TR
Tero
Kirsi
K
Salorinne
Heli
H
Lehtivuori
Janne A
JA
Ihalainen
Maija
M
Nissinen
D001572:Benzofurans / Q000138:chemical synthesis / Q000737:chemistry*; D047250:Calixarenes / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D018360:Crystallography, X-Ray; D005453:Fluorescence; D008968:Molecular Conformation; D015394:Molecular Structure; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D013329:Structure-Activity Relationship
D001572:Benzofurans; C466160:resorcinarene; D047250:Calixarenes; D010649:Phenylalanine; C105430:benzofuran
X-ray diffraction; benzofuran; calixarenes; fluorescence; resorcinarenes; supramolecular chemistry