| Synthesis of 5,15-diaryltetrabenzoporphyrins. | |
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MedLine Citation:
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PMID: 18452337 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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A general method of synthesis of 5,15-diaryltetrabenzoporphyrins (Ar 2TBPs) has been developed, based on 2 + 2 condensation of dipyrromethanes followed by oxidative aromatization. Two pathways to Ar 2TBPs were investigated: the tetrahydroisoindole pathway and the dihydroisoindole pathway. In the tetrahydroisoindole pathway, precursor 5,15-diaryltetracyclohexenoporphyrins (5,15-Ar 2TCHPs) were assembled from cyclohexeno-fused meso-unsubstituted dipyrromethanes and aromatic aldehydes or, alternatively, by way of the classical MacDonald synthesis. In the first case, scrambling was observed. Aromatization by tetracyclone was more effective than aromatization by DDQ but failed in the cases of porphyrins with electron-withdrawing substituents in the meso-aryl rings. The dihydroisoindole pathway was found to be much superior to the tetrahydroisoindole pathway, and it was developed into a general preparative method, consisting of (1) the synthesis of 4,7-dihydroisoindole and its transformation into meso-unsubstituted dipyrromethanes, (2) the synthesis of 5,15-diaryloctahydrotetrabenzoporphyrins (5,15-Ar 2OHTBPs), and (3) their subsequent aromatization by DDQ. Ar 2TBP free bases exhibit optical absorption spectra similar to those of meso-unsubstituted tetrabenzoporphyrins and fluoresce with high quantum yields. Pd complex of Ph 2TBP was found to be highly phosphorescent at room temperature. |
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Authors:
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Mikhail A Filatov; Artem Y Lebedev; Sergei A Vinogradov; Andrei V Cheprakov |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't Date: 2008-05-02 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 73 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2008 Jun |
Date Detail:
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Created Date: 2008-06-02 Completed Date: 2008-08-21 Revised Date: 2010-12-03 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 4175-85 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Moscow State University, Moscow 119899, Russia. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Magnetic Resonance Spectroscopy Mass Spectrometry / methods Porphyrins / chemical synthesis* Spectrophotometry, Ultraviolet |
| Grant Support | |
ID/Acronym/Agency:
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EB 007279/EB/NIBIB NIH HHS; HL 081273/HL/NHLBI NIH HHS; R01 EB007279-02/EB/NIBIB NIH HHS; R01 HL081273-01A1/HL/NHLBI NIH HHS; R01 HL081273-02/HL/NHLBI NIH HHS; R01 HL081273-03/HL/NHLBI NIH HHS; R01 NS031465-13A2/NS/NINDS NIH HHS; R01 NS031465-14/NS/NINDS NIH HHS; R01 NS031465-15/NS/NINDS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Porphyrins |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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