Coping Well with Crowding

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Science  20 Jan 2006:
Vol. 311, Issue 5759, pp. 307
DOI: 10.1126/science.311.5759.307a

Perylene bisimides, which are highly efficient and tunable fluorophores, are linear molecules with two imide groups (-CONRCO-) straddling the naphthalenic ends. Ilhan et al. report the synthesis of “Z-shaped” analogs in which the imide groups attach symmetrically but to only one aromatic ring each on opposite sides of the molecule, through the Diels-Alder trapping of a diketone-substituted anthracene with N-octylmaleimide, which produces o-xylyenols. Subsequent dehydration and aromatization steps yielded the Z-shaped bisimides; the more crowded substitution pattern as compared to the linear isomers causes twisting of the perylene core. Despite this twisting, the absorption and emission spectra show only a slight blue shift. This route should allow the synthesis of other perylene bisimides substituted at the imide and phenyl positions. — PDS

J. Am. Chem. Soc. 10.1021/ja056912o (2005).

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