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Synthesis, Characterization, and Electronic Structures of Porphyrins Fused with Polycyclic Aromatic Ring Systems
Author(s) -
Okujima Tetsuo,
Mack John,
Nakamura Jun,
Kubheka Gugu,
Nyokong Tebello,
Zhu Hua,
Komobuchi Naoki,
Ono Noboru,
Yamada Hiroko,
Uno Hidemitsu,
Kobayashi Nagao
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201602213
Subject(s) - acenaphthylene , porphyrin , magnetic circular dichroism , ring (chemistry) , molecular orbital , chemistry , circular dichroism , atomic orbital , polycyclic aromatic hydrocarbon , characterization (materials science) , computational chemistry , photochemistry , spectral line , crystallography , materials science , molecule , physics , organic chemistry , nanotechnology , electron , naphthalene , quantum mechanics , astronomy
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.