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The porphyrin moiety and the axial ligands in these compounds contain different combinations of complimentary molecular recognition functions. The former bears <jats:italic>p<\/jats:italic>\u2010iodophenyl, <jats:italic>p<\/jats:italic>\u2010bromophenyl, 4\u2032\u2010pyridyl, or 3\u2032\u2010pyridyl substituents at the <jats:italic>meso<\/jats:italic> positions of the porphyrin ring. The latter comprises either a carboxylate or hydroxy anchor for attachment to the porphyrin\u2010inserted tin ion and a pyridyl\u2010, benzotriazole\u2010, or halophenyl\u2010type aromatic residue as the potential binding site. The various complexes were structurally analyzed by single\u2010crystal X\u2010ray diffraction, accompanied by computational modeling evaluations. Halogen\u2010bonding interactions between the lateral aryl substituents of one unit of the porphyrin complex and the axial ligands of neighboring moieties was successfully expressed in several of the resulting samples. Their occurrence is affected by structural (for example, specific geometry of the six\u2010coordinate complexes) and electronic effects (for example, charge densities and electrostatic potentials). The shortest intermolecular I\u22c5\u22c5\u22c5N halogen\u2010bonding distance of 2.991\u2005\u00c5 was observed between iodophenyl (porphyrin) and benzotriazole (axial ligand) moieties. Manifestation of halogen bonds in these relatively bulky compounds without further activation of the halophenyl donor groups by electron\u2010withdrawing substituents is particularly remarkable.<\/jats:p>","DOI":"10.1002\/chem.201301857","type":"journal-article","created":{"date-parts":[[2013,9,13]],"date-time":"2013-09-13T11:38:54Z","timestamp":1379072334000},"page":"14941-14949","source":"Crossref","is-referenced-by-count":54,"title":["Exploring Supramolecular Self\u2010Assembly of Tetraarylporphyrins by Halogen Bonding: Crystal Engineering with Diversely Functionalized Six\u2010Coordinate Tin(L)<sub>2<\/sub>\u2013Porphyrin Tectons"],"prefix":"10.1002","volume":"19","author":[{"given":"Hatem 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