Novel peripherally functionalized seco-porphyrazines: Synthesis, characterization and spectroscopic evaluation

Efstathia G. Sakellariou; Antonio Garrido Montalban; Scott L. Beall; David Henderson; Hubert G. Meunier; David Phillips; Klaus Suhling; Anthony G.M. Barrett; Brian M. Hoffman

doi:10.1016/j.tet.2003.09.060

Novel peripherally functionalized seco-porphyrazines: Synthesis, characterization and spectroscopic evaluation

Efstathia G. Sakellariou, Antonio Garrido Montalban, Scott L. Beall, David Henderson, Hubert G. Meunier, David Phillips, Klaus Suhling, Anthony G.M. Barrett^*, Brian M. Hoffman

^*Corresponding author for this work

Chemistry

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

40 Scopus citations

Abstract

Co-macrocyclizations of 2,3-dipropylmaleonitrile and 2,3-di-(4- (methoxycarbonyl)phenyl)maleonitrile, respectively, with N,N′-dibenzyl-N, N′-di-(11-tetrahydropyranyloxy-3,6,9-trioxo-undecyl))maleonitrile and N,N,N′,N′-tetramethylmaleonitrile were used to prepare derivatives of the 4,5-diamino-porphyrazine systems including the zinc(II) complexes. Subsequent oxidation of the macrocycles with potassium permanganate gave the corresponding seco-porphyrazines. These were shown to be efficient sensitizers for the production of singlet oxygen (Φ_Δ=0.15-0.57) by the determination of their photophysical properties.

Original language	English (US)
Pages (from-to)	9083-9090
Number of pages	8
Journal	Tetrahedron
Volume	59
Issue number	46
DOIs	https://doi.org/10.1016/j.tet.2003.09.060
State	Published - Nov 10 2003

Keywords

Linstead macrocyclization
Porphyrazine
Sensitization
Singlet oxygen

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2003.09.060

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@article{d78655f50ec14f37b4ed3cab7a14994e,

title = "Novel peripherally functionalized seco-porphyrazines: Synthesis, characterization and spectroscopic evaluation",

abstract = "Co-macrocyclizations of 2,3-dipropylmaleonitrile and 2,3-di-(4- (methoxycarbonyl)phenyl)maleonitrile, respectively, with N,N′-dibenzyl-N, N′-di-(11-tetrahydropyranyloxy-3,6,9-trioxo-undecyl))maleonitrile and N,N,N′,N′-tetramethylmaleonitrile were used to prepare derivatives of the 4,5-diamino-porphyrazine systems including the zinc(II) complexes. Subsequent oxidation of the macrocycles with potassium permanganate gave the corresponding seco-porphyrazines. These were shown to be efficient sensitizers for the production of singlet oxygen (ΦΔ=0.15-0.57) by the determination of their photophysical properties.",

keywords = "Linstead macrocyclization, Porphyrazine, Sensitization, Singlet oxygen",

author = "Sakellariou, {Efstathia G.} and Montalban, {Antonio Garrido} and Beall, {Scott L.} and David Henderson and Meunier, {Hubert G.} and David Phillips and Klaus Suhling and Barrett, {Anthony G.M.} and Hoffman, {Brian M.}",

note = "Funding Information: We thank GlaxoSmithKline for the generous endowment to A. G. M. B., the EPSRC and NSF for support, and the Royal Society and the Wolfson Foundation for a Royal Society–Wolfson Research Merit Award (to A. G. M. B.) and for establishing the Wolfson center for Organic Chemistry in Medical Sciences at Imperial College London.",

year = "2003",

month = nov,

day = "10",

doi = "10.1016/j.tet.2003.09.060",

language = "English (US)",

volume = "59",

pages = "9083--9090",

journal = "Tetrahedron",

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publisher = "Elsevier Limited",

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TY - JOUR

T1 - Novel peripherally functionalized seco-porphyrazines

T2 - Synthesis, characterization and spectroscopic evaluation

AU - Sakellariou, Efstathia G.

AU - Montalban, Antonio Garrido

AU - Beall, Scott L.

AU - Henderson, David

AU - Meunier, Hubert G.

AU - Phillips, David

AU - Suhling, Klaus

AU - Barrett, Anthony G.M.

AU - Hoffman, Brian M.

N1 - Funding Information: We thank GlaxoSmithKline for the generous endowment to A. G. M. B., the EPSRC and NSF for support, and the Royal Society and the Wolfson Foundation for a Royal Society–Wolfson Research Merit Award (to A. G. M. B.) and for establishing the Wolfson center for Organic Chemistry in Medical Sciences at Imperial College London.

PY - 2003/11/10

Y1 - 2003/11/10

N2 - Co-macrocyclizations of 2,3-dipropylmaleonitrile and 2,3-di-(4- (methoxycarbonyl)phenyl)maleonitrile, respectively, with N,N′-dibenzyl-N, N′-di-(11-tetrahydropyranyloxy-3,6,9-trioxo-undecyl))maleonitrile and N,N,N′,N′-tetramethylmaleonitrile were used to prepare derivatives of the 4,5-diamino-porphyrazine systems including the zinc(II) complexes. Subsequent oxidation of the macrocycles with potassium permanganate gave the corresponding seco-porphyrazines. These were shown to be efficient sensitizers for the production of singlet oxygen (ΦΔ=0.15-0.57) by the determination of their photophysical properties.

AB - Co-macrocyclizations of 2,3-dipropylmaleonitrile and 2,3-di-(4- (methoxycarbonyl)phenyl)maleonitrile, respectively, with N,N′-dibenzyl-N, N′-di-(11-tetrahydropyranyloxy-3,6,9-trioxo-undecyl))maleonitrile and N,N,N′,N′-tetramethylmaleonitrile were used to prepare derivatives of the 4,5-diamino-porphyrazine systems including the zinc(II) complexes. Subsequent oxidation of the macrocycles with potassium permanganate gave the corresponding seco-porphyrazines. These were shown to be efficient sensitizers for the production of singlet oxygen (ΦΔ=0.15-0.57) by the determination of their photophysical properties.

KW - Linstead macrocyclization

KW - Porphyrazine

KW - Sensitization

KW - Singlet oxygen

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M3 - Article

AN - SCOPUS:0142258283

SN - 0040-4020

VL - 59

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JO - Tetrahedron

JF - Tetrahedron

IS - 46

ER -

Novel peripherally functionalized seco-porphyrazines: Synthesis, characterization and spectroscopic evaluation

Abstract

Keywords

ASJC Scopus subject areas

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