Hydrogenated tetraazaporphyrins--old but new core-modified phthalocyanine analogues

Dalton Transactions : an International Journal of Inorganic Chemistry
Takamitsu Fukuda, Nagao Kobayashi

Abstract

The synthesis, and spectroscopic and electrochemical properties of hydrogenated tetraazaporphyrins (TAPs), namely tetraazachlorins (TACs), tetraazabacteriochlorins (TABCs) and tetraazaisobacteriochlorins (TAiBCs), have been reviewed. While the first synthesis of this type of hydrogenated aromatic macrocycle was achieved as early as 1958 by Linstead et al. (G. E. Ficken, R. P. Linstead, E. Stephen and M. Whalley, J. Chem. Soc., 1958, 3879), the development of modern synthetic strategies enables us to isolate stable forms of the hydrogenated TAP derivatives. Benzo-, 2,3-naphtho- and 1,2-naphtho-fused derivatives were synthesized extensively, and all structural isomers have been elucidated. The chemical structures have been characterized using a variety of techniques, including mass spectrometry, (1)H and (13)C NMR, X-ray crystallography and IR spectroscopy. The spectroscopic properties (e.g., electronic absorption, magnetic circular dichroism (MCD), and fluorescence) of these compounds differ significantly from those of the original TAPs, or phthalocyanines (Pcs), due to the symmetry-lowering effects of the core aromatic macrocycles. The experimentally observed properties have been rationalized on the basis of electrochemical stu...Continue Reading

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Citations

Aug 9, 2016·Chemical Reviews·Masahiko Taniguchi, Jonathan S Lindsey
Mar 4, 2009·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Ida LanzoEmilia Sicilia
Apr 17, 2010·Chemistry, an Asian Journal·Sang Uck LeeYoshiyuki Kawazoe
Mar 29, 2012·Chemical Communications : Chem Comm·Soji ShimizuNagao Kobayashi
Apr 18, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Lijuan YuXingguo Li
Dec 24, 2010·Chemical Reviews·John Mack, Nagao Kobayashi

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