ROM polymerization-capture-release strategy for the chromatography-free synthesis of novel unsymmetrical porphyrazines

Matthew J. Fuchter; Benjamin J. Vesper; Karen A. Murphy; Hazel A. Collins; David Phillips; Anthony G.M. Barrett; Brian M. Hoffman

doi:10.1021/jo047792q

ROM polymerization-capture-release strategy for the chromatography-free synthesis of novel unsymmetrical porphyrazines

Matthew J. Fuchter, Benjamin J. Vesper, Karen A. Murphy, Hazel A. Collins, David Phillips, Anthony G.M. Barrett^*, Brian M. Hoffman

^*Corresponding author for this work

Chemistry

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24 Scopus citations

Abstract

(Chemical Equation Presented) Crossover-Linstead macrocyclization reactions of two norbornenyl-tagged diaminomaleonitriles with dipropylmaleonitrile gave access to crude mixtures of porphyrazines containing diamino-hexapropyl- porphyrazine magnesium complexes. The mixtures were subjected to ring-opening metathesis polymerization to yield the insoluble diaminoporphyrazine- functionalized polymers. Acid-mediated cleavage from the polymer backbone followed by acylation of the resultant sensitive macrocyclic diamines gave monoacetyl-, monotrifluoroacetyl-, and ditrifluoroacetyl-substituted porphyrazinediamines. Conversion of these amido-porphyrazines to the corresponding zinc macrocycles and studies of their electronic absorption and emission spectra, electrochemistry, and photophysics are described.

Original language	English (US)
Pages (from-to)	2793-2802
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	70
Issue number	7
DOIs	https://doi.org/10.1021/jo047792q
State	Published - Apr 1 2005

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo047792q

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title = "ROM polymerization-capture-release strategy for the chromatography-free synthesis of novel unsymmetrical porphyrazines",

abstract = "(Chemical Equation Presented) Crossover-Linstead macrocyclization reactions of two norbornenyl-tagged diaminomaleonitriles with dipropylmaleonitrile gave access to crude mixtures of porphyrazines containing diamino-hexapropyl- porphyrazine magnesium complexes. The mixtures were subjected to ring-opening metathesis polymerization to yield the insoluble diaminoporphyrazine- functionalized polymers. Acid-mediated cleavage from the polymer backbone followed by acylation of the resultant sensitive macrocyclic diamines gave monoacetyl-, monotrifluoroacetyl-, and ditrifluoroacetyl-substituted porphyrazinediamines. Conversion of these amido-porphyrazines to the corresponding zinc macrocycles and studies of their electronic absorption and emission spectra, electrochemistry, and photophysics are described.",

author = "Fuchter, {Matthew J.} and Vesper, {Benjamin J.} and Murphy, {Karen A.} and Collins, {Hazel A.} and David Phillips and Barrett, {Anthony G.M.} and Hoffman, {Brian M.}",

year = "2005",

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doi = "10.1021/jo047792q",

language = "English (US)",

volume = "70",

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journal = "Journal of Organic Chemistry",

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publisher = "American Chemical Society",

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ROM polymerization-capture-release strategy for the chromatography-free synthesis of novel unsymmetrical porphyrazines. / Fuchter, Matthew J.; Vesper, Benjamin J.; Murphy, Karen A.; Collins, Hazel A.; Phillips, David; Barrett, Anthony G.M.; Hoffman, Brian M.

In: Journal of Organic Chemistry, Vol. 70, No. 7, 01.04.2005, p. 2793-2802.

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

TY - JOUR

T1 - ROM polymerization-capture-release strategy for the chromatography-free synthesis of novel unsymmetrical porphyrazines

AU - Fuchter, Matthew J.

AU - Vesper, Benjamin J.

AU - Murphy, Karen A.

AU - Collins, Hazel A.

AU - Phillips, David

AU - Barrett, Anthony G.M.

AU - Hoffman, Brian M.

PY - 2005/4/1

Y1 - 2005/4/1

N2 - (Chemical Equation Presented) Crossover-Linstead macrocyclization reactions of two norbornenyl-tagged diaminomaleonitriles with dipropylmaleonitrile gave access to crude mixtures of porphyrazines containing diamino-hexapropyl- porphyrazine magnesium complexes. The mixtures were subjected to ring-opening metathesis polymerization to yield the insoluble diaminoporphyrazine- functionalized polymers. Acid-mediated cleavage from the polymer backbone followed by acylation of the resultant sensitive macrocyclic diamines gave monoacetyl-, monotrifluoroacetyl-, and ditrifluoroacetyl-substituted porphyrazinediamines. Conversion of these amido-porphyrazines to the corresponding zinc macrocycles and studies of their electronic absorption and emission spectra, electrochemistry, and photophysics are described.

AB - (Chemical Equation Presented) Crossover-Linstead macrocyclization reactions of two norbornenyl-tagged diaminomaleonitriles with dipropylmaleonitrile gave access to crude mixtures of porphyrazines containing diamino-hexapropyl- porphyrazine magnesium complexes. The mixtures were subjected to ring-opening metathesis polymerization to yield the insoluble diaminoporphyrazine- functionalized polymers. Acid-mediated cleavage from the polymer backbone followed by acylation of the resultant sensitive macrocyclic diamines gave monoacetyl-, monotrifluoroacetyl-, and ditrifluoroacetyl-substituted porphyrazinediamines. Conversion of these amido-porphyrazines to the corresponding zinc macrocycles and studies of their electronic absorption and emission spectra, electrochemistry, and photophysics are described.

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ROM polymerization-capture-release strategy for the chromatography-free synthesis of novel unsymmetrical porphyrazines

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