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

研究成果: Article査読

4 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)1355-1362
ページ数8
ジャーナルChemical and Pharmaceutical Bulletin
59
11
DOI
出版ステータスPublished - 2011 11
外部発表はい

ASJC Scopus subject areas

  • 化学 (全般)
  • 創薬

フィンガープリント

「Photochemical cleavage reaction of 8-quinolinyl sulfonates that are halogenated and nitrated at the 7-position」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル