Synthesis and characterizations of meso-disubstituted asymmetric porphycenes

Masatsugu Taneda; Akihiro Tanaka; Hisashi Shimakoshi; Atsushi Ikegami; Koichi Hashimoto; Masaaki Abe; Yoshio Hisaeda

doi:10.1016/j.tetlet.2013.08.026

Synthesis and characterizations of meso-disubstituted asymmetric porphycenes

Masatsugu Taneda, Akihiro Tanaka, Hisashi Shimakoshi, Atsushi Ikegami, Koichi Hashimoto, Masaaki Abe, Yoshio Hisaeda

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

10 Citations (Scopus)

Abstract

A post-synthetic method has been developed to synthesize novel asymmetric porphycenes bearing two different substituents on the meso-positions. Nitration of 9-acetoxy-2,7,12,17-tetra-n-propylporphycene with AgNO₃ in CH ₃COOH/CH₂Cl₂ occurs regioselectively at the 19-position of the macrocycle to give 9-acetoxy-19-nitro-2,7,12,17-tetra-n- propylporphycene (3a) which was readily converted to 9-acetoxy-19-amino-2,7,12, 17-tetra-n-propylporphycene (4a) by the reduction with SnCl₂ in pyridine.

Original language	English
Pages (from-to)	5727-5729
Number of pages	3
Journal	Tetrahedron Letters
Volume	54
Issue number	42
DOIs	https://doi.org/10.1016/j.tetlet.2013.08.026
Publication status	Published - Oct 16 2013

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2013.08.026

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@article{66bd70943f53481e94816439c60abf3f,

title = "Synthesis and characterizations of meso-disubstituted asymmetric porphycenes",

abstract = "A post-synthetic method has been developed to synthesize novel asymmetric porphycenes bearing two different substituents on the meso-positions. Nitration of 9-acetoxy-2,7,12,17-tetra-n-propylporphycene with AgNO3 in CH 3COOH/CH2Cl2 occurs regioselectively at the 19-position of the macrocycle to give 9-acetoxy-19-nitro-2,7,12,17-tetra-n- propylporphycene (3a) which was readily converted to 9-acetoxy-19-amino-2,7,12, 17-tetra-n-propylporphycene (4a) by the reduction with SnCl2 in pyridine.",

author = "Masatsugu Taneda and Akihiro Tanaka and Hisashi Shimakoshi and Atsushi Ikegami and Koichi Hashimoto and Masaaki Abe and Yoshio Hisaeda",

note = "Funding Information: This work was supported by a research fund from the Nissan Chemical Industries, Ltd , Grants-in-Aid for Scientific Research on Innovative Areas {\textquoteleft}Molecular Activation{\textquoteright} (No. 25105537 ) and {\textquoteleft}Coordination Programming{\textquoteright} (No. 24108730 ), Grants-in-Aid for Scientific Research (A) (No. 21245016 ) and (B) (No. 25288031 ), and the Global COE Program {\textquoteleft}Science for Future Molecular Systems{\textquoteright} from MEXT. The authors thank Professor Hiroyuki Furuta (Kyushu University) for measurements of the NIR spectra. ",

year = "2013",

month = oct,

day = "16",

doi = "10.1016/j.tetlet.2013.08.026",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - Synthesis and characterizations of meso-disubstituted asymmetric porphycenes

AU - Taneda, Masatsugu

AU - Tanaka, Akihiro

AU - Shimakoshi, Hisashi

AU - Ikegami, Atsushi

AU - Hashimoto, Koichi

AU - Abe, Masaaki

AU - Hisaeda, Yoshio

N1 - Funding Information: This work was supported by a research fund from the Nissan Chemical Industries, Ltd , Grants-in-Aid for Scientific Research on Innovative Areas ‘Molecular Activation’ (No. 25105537 ) and ‘Coordination Programming’ (No. 24108730 ), Grants-in-Aid for Scientific Research (A) (No. 21245016 ) and (B) (No. 25288031 ), and the Global COE Program ‘Science for Future Molecular Systems’ from MEXT. The authors thank Professor Hiroyuki Furuta (Kyushu University) for measurements of the NIR spectra.

PY - 2013/10/16

Y1 - 2013/10/16

N2 - A post-synthetic method has been developed to synthesize novel asymmetric porphycenes bearing two different substituents on the meso-positions. Nitration of 9-acetoxy-2,7,12,17-tetra-n-propylporphycene with AgNO3 in CH 3COOH/CH2Cl2 occurs regioselectively at the 19-position of the macrocycle to give 9-acetoxy-19-nitro-2,7,12,17-tetra-n- propylporphycene (3a) which was readily converted to 9-acetoxy-19-amino-2,7,12, 17-tetra-n-propylporphycene (4a) by the reduction with SnCl2 in pyridine.

AB - A post-synthetic method has been developed to synthesize novel asymmetric porphycenes bearing two different substituents on the meso-positions. Nitration of 9-acetoxy-2,7,12,17-tetra-n-propylporphycene with AgNO3 in CH 3COOH/CH2Cl2 occurs regioselectively at the 19-position of the macrocycle to give 9-acetoxy-19-nitro-2,7,12,17-tetra-n- propylporphycene (3a) which was readily converted to 9-acetoxy-19-amino-2,7,12, 17-tetra-n-propylporphycene (4a) by the reduction with SnCl2 in pyridine.

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JO - Tetrahedron Letters

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Synthesis and characterizations of meso-disubstituted asymmetric porphycenes

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