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rdf:type
lifeskim:mentions
pubmed:issue
35
pubmed:dateCreated
2008-8-27
pubmed:abstractText
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 studies and quantum chemical calculations. As an application of the TAC skeleton, the synthesis and electronic structures of tribenzo TAC (TBTAC)-C(60) conjugates, in which both components are covalently connected directly and thus show remarkable molecular orbital (MO) mixing between the constituting moieties, have also been reviewed.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Sep
pubmed:issn
1477-9234
pubmed:author
pubmed:issnType
Electronic
pubmed:day
21
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
4685-704
pubmed:meshHeading
pubmed:year
2008
pubmed:articleTitle
Hydrogenated tetraazaporphyrins--old but new core-modified phthalocyanine analogues.
pubmed:affiliation
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, 980-8578, Japan.
pubmed:publicationType
Journal Article, Review, Research Support, Non-U.S. Gov't