@article{SengeDahmsHoldtetal.2015, author = {Senge, Mathias O. and Dahms, Katja and Holdt, Hans-J{\"u}rgen and Kelling, Alexandra}, title = {Porphyrin substituent regiochemistry, conformation and packing - the case of 5,10-diphenylporphyrin}, series = {Zeitschrift f{\"u}r Naturforschung : B, Chemical sciences}, volume = {70}, journal = {Zeitschrift f{\"u}r Naturforschung : B, Chemical sciences}, number = {2}, publisher = {De Gruyter}, address = {T{\"u}bingen}, issn = {0932-0776}, doi = {10.1515/znb-2014-0217}, pages = {119 -- 123}, year = {2015}, abstract = {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.}, language = {en} }