Optical, electrochemical, and magnetic properties of pyrrole- And thiophene-bridged 5,15-diazaporphyrin dimers

Satoshi Omomo, Yasuhisa Maruyama, Ko Furukawa, Taniyuki Furuyama, Haruyuki Nakano, Nagao Kobayashi, Yoshihiro Matano

Research output: Contribution to journalArticle

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Abstract

The first examples of pyrrole- and thiophenebridged 5,15-diazaporphyrin (DAP) dimers are prepared through Stille coupling reactions of nickel(II) and copper(II) complexes of 3-bromo-10,20-dimesityl-5,15-diazaporphyrin (mesityl = 2,4,6-trimethylphenyl) with the respective 2,5-bis-(tributylstannyl)heteroles. The effects of the heterole spacers and meso nitrogen atoms on the optical, electrochemical, and magnetic properties of the DAP dimers are investigated by UV/Vis absorption spectroscopy, density functional theory calculations, magnetic circular dichroism spectroscopy, cyclic voltammetry, and EPR spectroscopy. The heterole spacers are found to have a significant impact on the electronic transitions over the entire p-system. In particular, the pyrrolebridged DAP dimers exhibit high light-harvesting potential in the low-energy visible/near-infrared region owing to the intrinsic charge-transfer character of the lowest excitation.

Original languageEnglish
Pages (from-to)2003-2010
Number of pages8
JournalChemistry - A European Journal
Volume21
Issue number5
DOIs
Publication statusPublished - Jan 26 2015

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Thiophenes
Pyrroles
Thiophene
Electrochemical properties
Dimers
Magnetic properties
Optical properties
Circular dichroism spectroscopy
Nickel
Ultraviolet spectroscopy
Absorption spectroscopy
Cyclic voltammetry
Density functional theory
Paramagnetic resonance
Charge transfer
Copper
Nitrogen
Spectroscopy
Infrared radiation
Atoms

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

Optical, electrochemical, and magnetic properties of pyrrole- And thiophene-bridged 5,15-diazaporphyrin dimers. / Omomo, Satoshi; Maruyama, Yasuhisa; Furukawa, Ko; Furuyama, Taniyuki; Nakano, Haruyuki; Kobayashi, Nagao; Matano, Yoshihiro.

In: Chemistry - A European Journal, Vol. 21, No. 5, 26.01.2015, p. 2003-2010.

Research output: Contribution to journalArticle

Omomo, Satoshi ; Maruyama, Yasuhisa ; Furukawa, Ko ; Furuyama, Taniyuki ; Nakano, Haruyuki ; Kobayashi, Nagao ; Matano, Yoshihiro. / Optical, electrochemical, and magnetic properties of pyrrole- And thiophene-bridged 5,15-diazaporphyrin dimers. In: Chemistry - A European Journal. 2015 ; Vol. 21, No. 5. pp. 2003-2010.
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AU - Furuyama, Taniyuki

AU - Nakano, Haruyuki

AU - Kobayashi, Nagao

AU - Matano, Yoshihiro

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