A fluoresceinophane: 1(9),4,16-trioxa-1(2,10)-anthracena-2(1,2)-benzenacyclohexadecaphane-1(7),3(1(9)H)-dione.
A novel macrocycle containing fluorescein, the highly fluorescent title compound, C(31)H(32)O(5), has a xanthene core and a benzyl unit that are planar. The latter is rotated by 72.99 (3) degrees from the xanthene mean plane. The C(11) alkyl tether and the xanthene group adopt a cage-like structure and the xanthene adopts a quinoid-type configuration. The compound crystallizes as a racemic mixture with one molecule of each isomer per unit cell. Even though the planes described by the xanthene and the benzene rings of different molecules are separated by 3.341 (4) and 3.73 (1) A, respectively, there is insufficient overlap between the aryl units to promote pi-stacking.
Dufresne
Stéphane
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Department of Chemistry, University of Montreal, Montréal, Québec, Canada.
Pérez Guarìn
Sergio Andrés
SA
Skene
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