Ham. Biemans et al., HEXAKIS PORPHYRINATO BENZENES - A NEW CLASS OF PORPHYRIN ARRAYS, Journal of the American Chemical Society, 120(43), 1998, pp. 11054-11060
A new type of porphyrin array has been synthesized by the coupling of
six porphyrin moieties to a central benzene core via an ether linkage.
The resulting porphryin supermolecule has a diameter up to 80 PI. and
a mass of 8500 daltons. In solution, the six porphyrins around the ce
ntral benzene ring arrange themselves into three sets of offset overla
pping dimers, which are rapidly interconverting at room temperature. S
olution UV-vis and fluorescence studies, however, indicate that there
are no electronic interactions between the individual porphyrin molecu
les. Upon spreading a chloroform solution of these porphyrin molecules
on a surface, they self-assemble Co form ring-shaped architectures on
a micrometer scale. Near-field scanning optical microscopy studies re
veal that the porphyrin moieties within the rings have an ordered arra
ngement with respect to their position in the ring after the sample ha
s been annealed at 80 degrees C for 2 days.