Effect of substituents in directing the formation of benzochlorins and isobacteriochlorins in porphyrin and chlorin systems.
[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.
Mettath
S
S
Department of Nuclear Medicine, and Molecular & Cellular Biophysics, Roswell Park Cancer Institute, Buffalo, New York 14263, USA.
Li
G
G
Srikrishnan
T
T
Mehta
R
R
Grossman
Z D
ZD
Dougherty
T J
TJ
Pandey
R K
RK
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*
D011166:Porphyrins; C006969:chlorin; D005461:Fluorine