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

Sashikumar Mettath; Guolin Li; Thamarapu Srikrishnan; Ricky Mehta; Zachary D. Grossman; Thomas J. Dougherty; Ravindra K. Pandey

doi:10.1021/ol990311i

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

Sashikumar Mettath
, Guolin Li
, Thamarapu Srikrishnan
, Ricky Mehta
, Zachary D. Grossman
, Thomas J. Dougherty
, Ravindra K. Pandey

Institute for Lasers Photonics and Biophotonics

Roswell Park Cancer Institute

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

Abstract

(matrix presented) 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.

Original language	English
Pages (from-to)	1961-1964
Number of pages	4
Journal	Organic Letters
Volume	1
Issue number	12
DOIs	https://doi.org/10.1021/ol990311i
State	Published - Dec 16 1999

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10.1021/ol990311i

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title = "Effect of Substituents in Directing the Formation of Benzochlorins and Isobacteriochlorins in Porphyrin and Chlorin Systems",

abstract = "(matrix presented) 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.",

author = "Sashikumar Mettath and Guolin Li and Thamarapu Srikrishnan and Ricky Mehta and Grossman, \{Zachary D.\} and Dougherty, \{Thomas J.\} and Pandey, \{Ravindra K.\}",

year = "1999",

month = dec,

day = "16",

doi = "10.1021/ol990311i",

language = "English",

volume = "1",

pages = "1961--1964",

journal = "Organic Letters",

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publisher = "American Chemical Society",

number = "12",

}

TY - JOUR

T1 - Effect of Substituents in Directing the Formation of Benzochlorins and Isobacteriochlorins in Porphyrin and Chlorin Systems

AU - Mettath, Sashikumar

AU - Li, Guolin

AU - Srikrishnan, Thamarapu

AU - Mehta, Ricky

AU - Grossman, Zachary D.

AU - Dougherty, Thomas J.

AU - Pandey, Ravindra K.

PY - 1999/12/16

Y1 - 1999/12/16

N2 - (matrix presented) 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.

AB - (matrix presented) 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.

UR - https://www.scopus.com/pages/publications/0033576421

U2 - 10.1021/ol990311i

DO - 10.1021/ol990311i

M3 - Article

C2 - 10836054

AN - SCOPUS:0033576421

SN - 1523-7060

VL - 1

SP - 1961

EP - 1964

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

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

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