title: Effect of substituents in directing the formation of benzochlorins and isobacteriochlorins in porphyrin and chlorin systems.
abstract: [formula: see text] 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.
authors.affiliation: Department of Nuclear Medicine, and Molecular & Cellular Biophysics, Roswell Park Cancer Institute, Buffalo, New York 14263, USA.
authors.forename: S
authors.initials: S
authors.lastname: Mettath
authors.forename: G
authors.initials: G
authors.lastname: Li
authors.forename: T
authors.initials: T
authors.lastname: Srikrishnan
authors.forename: R
authors.initials: R
authors.lastname: Mehta
authors.forename: Z D
authors.initials: ZD
authors.lastname: Grossman
authors.forename: T J
authors.initials: TJ
authors.lastname: Dougherty
authors.forename: R K
authors.initials: RK
authors.lastname: Pandey
mesh_terms: D018360:Crystallography, X-Ray; D003500:Cyclization; D005461:Fluorine / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010777:Photochemistry; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D011166:Porphyrins; C006969:chlorin; D005461:Fluorine