title: Incorporation of the 1,5-naphthalene subunit into heteroporphyrin structure: toward helical aceneporphyrinoids.
abstract: 5,10,15,20-Tetraaryl-22-hetero-1,5-naphthiporphyrins, which contain a 1,5-naphthylene moiety instead of one pyrrole embedded in the macrocyclic framework of heteroporphyrins, were obtained by the [3 + 1] approach using the 1,5-naphthylene analogue of tripyrrane (1,5-bis(phenyl(2-pyrolyl)methyl)naphthalene) and 2,5-bis(arylhydroxymethyl)heterocyclopentadiene (heterocyclopentadiene: thiophene, selenophene, tellurophene). The steric constraints, imposed by the substitution mode of the 1,5-naphthylene building block, resulted in the specific helical conformation of 22-hetero-1,5-naphthiporphyrins. The spectroscopic and structural properties of these aceneporphyrinoids indicate a lack of macrocycle aromaticity. Their protonation yielded solely dicationic species.
authors.affiliation: Department of Chemistry, University of Wrocław, 14 F. Joliot-Curie Street, 50-383 Wrocław, Poland.
authors.forename: Bartosz
authors.initials: B
authors.lastname: Szyszko
authors.forename: Ewa
authors.initials: E
authors.lastname: Pacholska-Dudziak
authors.forename: Lechosław
authors.initials: L
authors.lastname: Latos-Grażyński
mesh_terms: D008958:Models, Molecular; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry*; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D009281:Naphthalenes; D011166:Porphyrins