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Effects of interaction between the chelate rings and π‐conjugated systems in fused salphen complexes on UV‐Vis‐NIR spectra
Author(s) -
Houjou Hirohiko,
Yagi Keisuke,
Yoshikawa Isao,
Mutai Toshiki,
Araki Koji
Publication year - 2017
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3635
Subject(s) - chemistry , conjugated system , ring (chemistry) , acene , naphthalene , annulation , chelation , density functional theory , photochemistry , absorption spectroscopy , absorption (acoustics) , spectral line , solvent , aromaticity , computational chemistry , inorganic chemistry , organic chemistry , molecule , polymer , physics , quantum mechanics , astronomy , acoustics , catalysis
Dinuclear (Zn 2 , Ni 2 , and NiZn) complexes of fused salphen with acene‐type annelation were synthesized from 3,7‐diformyl‐2,6‐dihydroxynaphthalene. The spectroscopic properties of these complexes were compared with those of their constitutional isomers with phene‐type annelation. The acene‐type complexes exhibited a characteristic absorption band in the near‐infrared region that showed a noticeable solvent effect. Time‐dependent density functional theory calculations suggested that the absorption arose from a π → π* transition localized at the naphthalene ring, which was perturbed by the adjoining chelate rings. Effects of the connection topology in the fused salphen complexes are discussed by comparison with those of polycyclic aromatic hydrocarbons.