A series of substituted 2,3,5,6-tetraarylbenzo[1,2-b:5,4-b']difurans 1
was synthesized. This synthesis is based upon the photocyclization of
2,5-dibenzoylresorcinol dibenzyl ethers to the corresponding tetrahyd
robenzo[1,2-b:5,4-b']difurans. Treatment of the photoproducts with met
hanesulfonyl chloride in pyridine afforded 1 in overall yields ranging
from 30-72%. A number of these compounds have high fluorescence quant
um yields (phi(f) = 0.76-0.90), and their fluorescence spectra exhibit
large solvatochromic shifts. These compounds may be suitable for use
as fluorescent probes.