The structural diversity of benzofuran resorcinarene leads to enhanced fluorescence
Tero, T.-R., Salorinne, K., Lehtivuori, H., Ihalainen, J., & Nissinen, M. (2014). The structural diversity of benzofuran resorcinarene leads to enhanced fluorescence. Chemistry - An Asian Journal, 9 (7), 1860-1867. doi:10.1002/asia.201402016
Published inChemistry - An Asian Journal
© 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. This is a final draft version of an article whose final and definitive form has been published by Wiley. Published in this repository with the kind permission of the publisher.
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.