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Porphyrin substituent regiochemistry, conformation and packing - the case of 5,10-diphenylporphyrin
(2015)
5,10-Disubstituted porphyrins are more recent additions to the family of meso-substituted porphyrins. A crystallographic comparison of 5,10-diphenylporphyrin with the regioisomeric 5,15-disubstituted system reveals striking differences in their conformation. In the free base porphyrins the former uses mainly out-of-plane distortion to alleviate steric strain while in-plane core elongation predominates in the latter. In contrast, the structure of the Cu(II) complex is planar and forms strong p-p aggregates with very small lateral shifts. Macroscopically, the packing is similar to that of porphyrin sponges of the 5,10,15,20-tetraphenylporphyrin type.