title: Photochemical cleavage reaction of 8-quinolinyl sulfonates that are halogenated and nitrated at the 7-position.
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.
authors: Center for Technologies against Cancer, Tokyo University of Science, 2641 Yamazaki, Noda 278–8510, Japan.
authors: Shinya
authors: S
authors: Ariyasu
authors: Kengo
authors: K
authors: Hanaya
authors: Megumi
authors: M
authors: Tsunoda
authors: Masanori
authors: M
authors: Kitamura
authors: Masanori
authors: M
authors: Hayase
authors: Ryo
authors: R
authors: Abe
authors: Shin
authors: S
authors: Aoki
mesh_terms: D000476:Alkanesulfonates / Q000138:chemical synthesis / Q000737:chemistry*; D054879:Halogenation; D006863:Hydrogen-Ion Concentration; D008027:Light; D009566:Nitrates / Q000737:chemistry*; D010782:Photolysis; D011789:Quantum Theory; D012825:Silicon / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet
chemical_list: D000476:Alkanesulfonates; D009566:Nitrates; D012825:Silicon