Effect of Substituents in Directing the Formation of Benzochlorins and Isobacteriochlorins in Porphyrin and Chlorin Systems

A first synthesis of free-base fluorinated benzochlorins by acid-catalyzed cyclization of 20-(2-trisiloxy-trifluoromethylvinyl)octaethylporphyrin is achieved. Under similar reaction conditions, the purpurin-18-N-hexylimide analogues produced the corresponding fluorinated and nonfluorinated ethyliden...

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Published inOrganic letters Vol. 1; no. 12; pp. 1961 - 1964
Main Authors Mettath, Sashikumar, Li, Guolin, Srikrishnan, Thamarapu, Mehta, Ricky, Grossman, Zachary D, Dougherty, Thomas J, Pandey, Ravindra K
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.12.1999
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Crystallography, X-Ray
Cyclization
Fluorine - chemistry
Magnetic Resonance Spectroscopy
Mass Spectrometry
Photochemistry
Physical Sciences
Porphyrins - chemical synthesis
Porphyrins - chemistry
Science & Technology
CHLOROPHYLL-A
PHOTODYNAMIC THERAPY
EFFICACY
ANALOGS
DERIVATIVES
PHOTOSENSITIZERS
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Summary:A first synthesis of free-base fluorinated benzochlorins by acid-catalyzed cyclization of 20-(2-trisiloxy-trifluoromethylvinyl)octaethylporphyrin is achieved. Under similar reaction conditions, the purpurin-18-N-hexylimide analogues produced the corresponding fluorinated and nonfluorinated ethylidene-substituted isobacteriochlorins and fluorinated chlorin, respectively. The structure of the porphyrin based fluorinated benzochlorin was also confirmed by X-ray analysis.
Bibliography:Medline
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ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol990311i