Photochemical cleavage reaction of 8-quinolinyl sulfonates that are halogenated and nitrated at the 7-position

Shinya Ariyasu, Kengo Hanaya, Megumi Tsunoda, Masanori Kitamura, Masanori Hayase, Ryo Abe, Shin Aoki

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Photochemical bond-cleavage reactions are potentially useful in chemistry, bioorganic chemistry and medicinal chemistry. We previously reported on a photochemical cleavage reaction of 8-quinolinyl sulfonate (8-QS) derivatives in aqueous solution at neutral pH, which we proposed to proceed via an excited triplet state. In this report, we report on the synthesis of some new photocleavable 8-QS derivatives, in which halogen atoms or a nitro group was introduced at the 7-position, in an attempt to improve photoreactive properties and to produce a red-shift in the irradiation wavelength. The introduction of bromine and iodine resulted in an acceleration in the photoreaction by about 1.5 times, possibly due to a heavy atom effect. It was also found that 7-nitro-8-QS absorbs at >360 nm, and, as a result, the S-O bond of this compound can be cleaved by photoirradiation with a fluorescent lamp in aqueous solution and on silicon surface.

Original languageEnglish
Pages (from-to)1355-1362
Number of pages8
JournalChemical and Pharmaceutical Bulletin
Volume59
Issue number11
DOIs
Publication statusPublished - 2011 Nov 1
Externally publishedYes

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Keywords

  • 8-Quinolinol
  • Halogenation
  • Nitration
  • Photolysis
  • Sulfonate

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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