title: Synthesis, Characterization, and Electronic Structures of Porphyrins Fused with Polycyclic Aromatic Ring Systems.
abstract: A series of porphyrins fused with acenaphthylene, phenanthroline, and benzofluoranthene polycyclic aromatic rings were prepared by means of a 3+1 porphyrin synthesis approach and subsequent retro-Diels-Alder reaction of bicyclo[2.2.2]octadiene-fused precursors. Analysis of the magnetic circular dichroism spectra and the results of time-dependent DFT calculations are used to identify the reasons for the trends observed in the wavelengths and relative intensities of the Q bands of the products. Michl's perimeter model is used as a conceptual framework to explain the changes in the relative energies of the frontier π-molecular orbitals.
authors: Graduate School of Science and Engineering, Ehime University, Matsuyama, 790-8577, Japan. okujima.tetsuo.mu@ehime-u.ac.jp.
authors: Tetsuo
authors: T
authors: Okujima
authors: Department of Chemistry, Rhodes University, Grahamstown, 6410, South Africa. j.mack@ru.ac.za.
authors: John
authors: http://orcid.org/0000-0002-1345-9262
authors: J
authors: Mack
authors: Graduate School of Science and Engineering, Ehime University, Matsuyama, 790-8577, Japan.
authors: Jun
authors: J
authors: Nakamura
authors: Department of Chemistry, Rhodes University, Grahamstown, 6410, South Africa.
authors: Gugu
authors: G
authors: Kubheka
authors: Department of Chemistry, Rhodes University, Grahamstown, 6410, South Africa.
authors: Tebello
authors: T
authors: Nyokong
authors: Graduate School of Science, Tohoku University, Sendai, 980-8578, Japan.
authors: Hua
authors: H
authors: Zhu
authors: Graduate School of Science and Engineering, Ehime University, Matsuyama, 790-8577, Japan.
authors: Naoki
authors: N
authors: Komobuchi
authors: Graduate School of Science and Engineering, Ehime University, Matsuyama, 790-8577, Japan.
authors: Noboru
authors: N
authors: Ono
authors: Graduate School of Materials Science, Nara Institute of Science and Technology, Ikoma, 630-0192, Japan.
authors: Hiroko
authors: H
authors: Yamada
authors: Graduate School of Science and Engineering, Ehime University, Matsuyama, 790-8577, Japan.
authors: Hidemitsu
authors: H
authors: Uno
authors: Faculty of Textile Science and Technology, Shinshu University, Ueda, 386-8567, Japan. nagaok@shinshu-u.ac.jp.
authors: Nagao
authors: N
authors: Kobayashi
keywords: cycloaddition; density functional calculations; fused-ring systems; magnetic circular dichroism; porphyrinoids