Synthesis and spectroscopic and electrochemical studies of pyrazine-or pyridine-ring-fused tetraazachlorins, bacteriochlorins, and isobacteriochlorins

Elena A. Makarova, Ekaterina V. Dzyuina, Takamitsu Fukuda, Hironori Kaneko, Naoaki Hashimoto, Yuu Kikukawa, Nagao Kobayashi, Evgeny A. Lukyanets

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

Mixed condensation of tetramethylsuccinonitrile and either 2,3-dicyano-5,6-diethylpyrazine, 2,3-dicyanopyridine, or 3,4- pyridinedicarboximide in the presence of nickel chloride forms novel pyrazine-, 2, 3-pyridine-, or 3, 4-pyridine-ring-fused tetraazachlorin (TAC), tetraazabacteriochlorin (TABC), and tetraazaisobacteriochlorin (TAiBC) derivatives. All possible structural isomers were separated using repeated thin-layer chromatography and have been investigated by absorption and magnetic circular dichroism spectroscopy. Similarly to previously reported TAC analogues, the TAC and TABC derivatives show large splitting of the Q band, while a single, intense absorption band is observed for the TAiBC derivatives. Although the absorption spectra are practically identical in shape for the separated structural isomers of TACs and TABCs, the Q-band maxima of the TAiBCs depend significantly on their structures. The observed spectroscopic properties were interpreted on the basis of electrochemical data and the results of (time-dependent) DFT calculations.

Original languageEnglish
Pages (from-to)164-173
Number of pages10
JournalInorganic chemistry
Volume48
Issue number1
DOIs
Publication statusPublished - 2009 Jan 5

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry

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