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Long Oligofurans

Oligofurans were once too short, but now with as many as nine rings, they are back in vogue as electronic materials

by Celia Henry Arnaud
February 15, 2010 | A version of this story appeared in Volume 88, Issue 7

Credit: J. Am. Chem. Soc.
Packing of a six-ring α-oligofuran.
Credit: J. Am. Chem. Soc.
Packing of a six-ring α-oligofuran.

α-Oligofurans have been bypassed as electronic materials because scientists thought it wasn’t possible to make stable versions with more than five furan rings. Now, Michael Bendikov, Ori Gidron, and Yael Diskin-Posner of Israel’s Weizmann Institute of Science report the synthesis and characterization of α-oligofurans with as many as nine rings (J. Am. Chem. Soc., DOI: 10.1021/ja9093346). They made the oligomers by Stille coupling of shorter α-dibromooligofurans and monotin α-oligofurans. The long α-oligofurans have better fluorescence, solubility, packing, and rigidity than the corresponding oligothiophenes, which have been workhorses in organic electronics. “In the early days of conducting polymer research, the results with polyfuran were unimpressive and uninteresting, hence research on this material was not pursued,” says Fred Wudl, a materials chemist at the University of California, Santa Barbara. “Bendikov has shown, very elegantly, that indeed polyfuran should be revisited in all aspects related to organic electronics.”


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