Synthesis of porphyrazine-octaamine, hexamine and diamine derivatives

Matthew J. Fuchter; L. Scott Beall; Sven M. Baum; Antonio Garrido Montalban; Efstathia G. Sakellariou; Neelakandha S. Mani; Todd Miller; Benjamin J. Vesper; Andrew J.P. White; David J. Williams; Anthony G.M. Barrett; Brian M. Hoffman

doi:10.1016/j.tet.2005.03.090

Synthesis of porphyrazine-octaamine, hexamine and diamine derivatives

Matthew J. Fuchter, L. Scott Beall, Sven M. Baum, Antonio Garrido Montalban, Efstathia G. Sakellariou, Neelakandha S. Mani, Todd Miller, Benjamin J. Vesper, Andrew J.P. White, David J. Williams, Anthony G.M. Barrett^*, Brian M. Hoffman

^*Corresponding author for this work

Chemistry

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

49 Scopus citations

Abstract

The syntheses of a variety of substituted diaminomaleonitriles, with variable nitrogen substituents, were undertaken. Linstead macrocyclization of the resulting diaminomaleonitriles gave access to a wide range of functionalized porphyrazine-octaamines and hexamines and norphthalocyaninediamines. Conversion of these macrocycles into metallic derivatives and studies of their electronic absorption, solubility and electrochemistry are described. These flexible tetraazaporphyrins show potential in a range of applications including biomedical agents, novel charge-transfer complexes, chemical sensors, novel electronic materials and non-linear optics.

Original language	English (US)
Pages (from-to)	6115-6130
Number of pages	16
Journal	Tetrahedron
Volume	61
Issue number	25
DOIs	https://doi.org/10.1016/j.tet.2005.03.090
State	Published - Jun 20 2005

Funding

We thank GlaxoSmithKline for the generous endowment (to A.G.M.B.), the Royal Society and the Wolfson Foundation for a Royal Society Wolfson Research Merit Award (to A.G.M.B.), the Wolfson Foundation for establishing the Wolfson Centre for Organic Chemistry in Medical Sciences at Imperial College London, the Engineering and Physical Sciences Research Council, the National Science Foundation and Schering AG for generous support of our studies.

Keywords

Aminoporphyrazine
Electrochemistry
Linstead macrocyclization
Nickel porphyrazines
Porphyrazine
UV-vis spectroscopy

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2005.03.090

Cite this

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title = "Synthesis of porphyrazine-octaamine, hexamine and diamine derivatives",

abstract = "The syntheses of a variety of substituted diaminomaleonitriles, with variable nitrogen substituents, were undertaken. Linstead macrocyclization of the resulting diaminomaleonitriles gave access to a wide range of functionalized porphyrazine-octaamines and hexamines and norphthalocyaninediamines. Conversion of these macrocycles into metallic derivatives and studies of their electronic absorption, solubility and electrochemistry are described. These flexible tetraazaporphyrins show potential in a range of applications including biomedical agents, novel charge-transfer complexes, chemical sensors, novel electronic materials and non-linear optics.",

keywords = "Aminoporphyrazine, Electrochemistry, Linstead macrocyclization, Nickel porphyrazines, Porphyrazine, UV-vis spectroscopy",

author = "Fuchter, {Matthew J.} and Beall, {L. Scott} and Baum, {Sven M.} and Montalban, {Antonio Garrido} and Sakellariou, {Efstathia G.} and Mani, {Neelakandha S.} and Todd Miller and Vesper, {Benjamin J.} and White, {Andrew J.P.} and Williams, {David J.} 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 Royal Society and the Wolfson Foundation for a Royal Society Wolfson Research Merit Award (to A.G.M.B.), the Wolfson Foundation for establishing the Wolfson Centre for Organic Chemistry in Medical Sciences at Imperial College London, the Engineering and Physical Sciences Research Council, the National Science Foundation and Schering AG for generous support of our studies. ",

year = "2005",

month = jun,

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doi = "10.1016/j.tet.2005.03.090",

language = "English (US)",

volume = "61",

pages = "6115--6130",

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AU - Fuchter, Matthew J.

AU - Beall, L. Scott

AU - Baum, Sven M.

AU - Montalban, Antonio Garrido

AU - Sakellariou, Efstathia G.

AU - Mani, Neelakandha S.

AU - Miller, Todd

AU - Vesper, Benjamin J.

AU - White, Andrew J.P.

AU - Williams, David J.

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 Royal Society and the Wolfson Foundation for a Royal Society Wolfson Research Merit Award (to A.G.M.B.), the Wolfson Foundation for establishing the Wolfson Centre for Organic Chemistry in Medical Sciences at Imperial College London, the Engineering and Physical Sciences Research Council, the National Science Foundation and Schering AG for generous support of our studies.

PY - 2005/6/20

Y1 - 2005/6/20

N2 - The syntheses of a variety of substituted diaminomaleonitriles, with variable nitrogen substituents, were undertaken. Linstead macrocyclization of the resulting diaminomaleonitriles gave access to a wide range of functionalized porphyrazine-octaamines and hexamines and norphthalocyaninediamines. Conversion of these macrocycles into metallic derivatives and studies of their electronic absorption, solubility and electrochemistry are described. These flexible tetraazaporphyrins show potential in a range of applications including biomedical agents, novel charge-transfer complexes, chemical sensors, novel electronic materials and non-linear optics.

AB - The syntheses of a variety of substituted diaminomaleonitriles, with variable nitrogen substituents, were undertaken. Linstead macrocyclization of the resulting diaminomaleonitriles gave access to a wide range of functionalized porphyrazine-octaamines and hexamines and norphthalocyaninediamines. Conversion of these macrocycles into metallic derivatives and studies of their electronic absorption, solubility and electrochemistry are described. These flexible tetraazaporphyrins show potential in a range of applications including biomedical agents, novel charge-transfer complexes, chemical sensors, novel electronic materials and non-linear optics.

KW - Aminoporphyrazine

KW - Electrochemistry

KW - Linstead macrocyclization

KW - Nickel porphyrazines

KW - Porphyrazine

KW - UV-vis spectroscopy

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Synthesis of porphyrazine-octaamine, hexamine and diamine derivatives

Abstract

Funding

Keywords

ASJC Scopus subject areas

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CCDC 264429: Experimental Crystal Structure Determination

CCDC 264428: Experimental Crystal Structure Determination

Cite this

Synthesis of porphyrazine-octaamine, hexamine and diamine derivatives

Abstract

Funding

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 264429: Experimental Crystal Structure Determination

CCDC 264428: Experimental Crystal Structure Determination

Cite this