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Palladium Complexes of Carbazole‐Based Chalcogenaisophlorins: Synthesis, Structure, and Solid‐State NIR Absorption Spectra
Author(s) -
Maeda Chihiro,
Takaishi Kazuto,
Ema Tadashi
Publication year - 2017
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201700430
Subject(s) - chemistry , antiaromaticity , carbazole , palladium , dimer , intermolecular force , absorption (acoustics) , crystallography , absorption spectroscopy , infrared spectroscopy , annulation , spectroscopy , photochemistry , diffraction , molecule , organic chemistry , aromaticity , materials science , optics , physics , quantum mechanics , composite material , catalysis
Annulation reactions of the butadiyne‐bridged carbazole dimer 1 produced carbazole‐based chalcogenaisophlorins 2 – 4 , which were transformed into the corresponding palladium complexes 2Pd – 4Pd . The structures were characterized by NMR spectroscopy and X‐ray diffraction analysis. Metallation fixed the structures which displayed weak antiaromatic character derived from the 20π isophlorin framework. These complexes showed weak near‐infrared (NIR) absorption typical for antiaromatic porphyrinoids in solution. In addition, 2Pd and 3Pd showed relatively strong solid‐state NIR absorption. X‐ray diffraction analyses of 2Pd and 3Pd revealed trimeric and dimeric stacked layered structures, respectively, and DFT calculations suggest that the solid‐state NIR absorption is ascribed to intermolecular charge transfer.