Synthesis, Optical Properties, and Electronic Structures of Tetrakis(pentafluorophenyl)tetrathiaisophlorin Dioxide

Vijay Lakshmi Mishra, Taniyuki Furuyama, Nagao Kobayashi, Kenta Goto, Takaaki Miyazaki, Jye Shane Yang, Teruo Shinmyozu

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

The synthesis, structure, optical and redox properties, and electronic structure of tetrakis(pentafluorophenyl)tetrathiaisophlorin dioxide (12) are reported. Oxidation of tetrakis(pentafluorophenyl)tetrathiaisophlorin (11) with dimethyldioxirane afforded the oxidized product, which was the tetrathiaisophlorin with two thiophene 1-oxide moieties (12). More significant nonplanarity and greater bond length alternation in 12 than those of 11 were observed by X-ray structural analysis. The absorption spectrum of 12 contains two bands at λ=348 and 276 nm, with a weak tail that extends to λ≈650 nm. Analysis of the magnetic circular dichroism spectrum of 12, based on Michl's 4N-perimeter model and molecular orbital calculations, indicate that the broad band at λ=348 nm appears to contain N2and P2bands, and 12 is classified as a 4nπ system, similar to 11. The nuclear-independent chemical shift values and1H NMR spectroscopy data indicate that 12 has more antiaromatic character than 11.

Original languageEnglish
Pages (from-to)9190-9197
Number of pages8
JournalChemistry - A European Journal
Volume22
Issue number27
DOIs
Publication statusPublished - Jun 27 2016

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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