Bis(dimethylamino)porphyrazines: Synthetic, structural, and spectroscopic investigations

Antonio Garrido Montalban; Wade Jarrell; Eric Riguet; Quentin J. McCubbin; Mairin E. Anderson; Andrew J.P. White; David J. Williams; Anthony G.M. Barrett; Brian M. Huffman

doi:10.1021/jo991646g

Bis(dimethylamino)porphyrazines: Synthetic, structural, and spectroscopic investigations

Antonio Garrido Montalban, Wade Jarrell, Eric Riguet, Quentin J. McCubbin, Mairin E. Anderson, Andrew J.P. White, David J. Williams, Anthony G.M. Barrett^*, Brian M. Huffman

^*Corresponding author for this work

Chemistry

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Abstract

The synthesis and isolation of unsymmetrical porphyrazines bearing two, four, and six bis(dimethylamino) functionalities has been achieved via the base-catalyzed cross-condensation of 1,2-dicyanobenzene 8 and bis(dimethylamino)maleonitrile 7. In addition, the benzo-fused hexaaminoporphyrazine dimer 10 was prepared from condensation of dinitrile 7 (in excess) with benzenebis(1,3-diiminopyrroline) 9. Electrochemical studies reveal that all porphyrazines may be readily oxidized. The X-ray structures of porphyrazines 2b and 5a and the cis isomer 3a are presented. The latter is the first structure of a porphyrazine having a cis-type substitution pattern. The extended π-conjugation in dimer 10 causes a ~100 nm red-shifted Q-band in the electronic absorption spectrum.

Original language	English (US)
Pages (from-to)	2472-2478
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	65
Issue number	8
DOIs	https://doi.org/10.1021/jo991646g
State	Published - Apr 21 2000

ASJC Scopus subject areas

Organic Chemistry

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@article{815e6bb4a7a5458db5236adc258a5248,

title = "Bis(dimethylamino)porphyrazines: Synthetic, structural, and spectroscopic investigations",

abstract = "The synthesis and isolation of unsymmetrical porphyrazines bearing two, four, and six bis(dimethylamino) functionalities has been achieved via the base-catalyzed cross-condensation of 1,2-dicyanobenzene 8 and bis(dimethylamino)maleonitrile 7. In addition, the benzo-fused hexaaminoporphyrazine dimer 10 was prepared from condensation of dinitrile 7 (in excess) with benzenebis(1,3-diiminopyrroline) 9. Electrochemical studies reveal that all porphyrazines may be readily oxidized. The X-ray structures of porphyrazines 2b and 5a and the cis isomer 3a are presented. The latter is the first structure of a porphyrazine having a cis-type substitution pattern. The extended π-conjugation in dimer 10 causes a ~100 nm red-shifted Q-band in the electronic absorption spectrum.",

author = "{Garrido Montalban}, Antonio and Wade Jarrell and Eric Riguet and McCubbin, {Quentin J.} and Anderson, {Mairin E.} and White, {Andrew J.P.} and Williams, {David J.} and Barrett, {Anthony G.M.} and Huffman, {Brian M.}",

year = "2000",

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doi = "10.1021/jo991646g",

language = "English (US)",

volume = "65",

pages = "2472--2478",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Bis(dimethylamino)porphyrazines

T2 - Synthetic, structural, and spectroscopic investigations

AU - Garrido Montalban, Antonio

AU - Jarrell, Wade

AU - Riguet, Eric

AU - McCubbin, Quentin J.

AU - Anderson, Mairin E.

AU - White, Andrew J.P.

AU - Williams, David J.

AU - Barrett, Anthony G.M.

AU - Huffman, Brian M.

PY - 2000/4/21

Y1 - 2000/4/21

N2 - The synthesis and isolation of unsymmetrical porphyrazines bearing two, four, and six bis(dimethylamino) functionalities has been achieved via the base-catalyzed cross-condensation of 1,2-dicyanobenzene 8 and bis(dimethylamino)maleonitrile 7. In addition, the benzo-fused hexaaminoporphyrazine dimer 10 was prepared from condensation of dinitrile 7 (in excess) with benzenebis(1,3-diiminopyrroline) 9. Electrochemical studies reveal that all porphyrazines may be readily oxidized. The X-ray structures of porphyrazines 2b and 5a and the cis isomer 3a are presented. The latter is the first structure of a porphyrazine having a cis-type substitution pattern. The extended π-conjugation in dimer 10 causes a ~100 nm red-shifted Q-band in the electronic absorption spectrum.

AB - The synthesis and isolation of unsymmetrical porphyrazines bearing two, four, and six bis(dimethylamino) functionalities has been achieved via the base-catalyzed cross-condensation of 1,2-dicyanobenzene 8 and bis(dimethylamino)maleonitrile 7. In addition, the benzo-fused hexaaminoporphyrazine dimer 10 was prepared from condensation of dinitrile 7 (in excess) with benzenebis(1,3-diiminopyrroline) 9. Electrochemical studies reveal that all porphyrazines may be readily oxidized. The X-ray structures of porphyrazines 2b and 5a and the cis isomer 3a are presented. The latter is the first structure of a porphyrazine having a cis-type substitution pattern. The extended π-conjugation in dimer 10 causes a ~100 nm red-shifted Q-band in the electronic absorption spectrum.

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EP - 2478

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 8

ER -

Bis(dimethylamino)porphyrazines: Synthetic, structural, and spectroscopic investigations

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