Possible singlet oxygen generation from the photolysis of indigo dyes in methanol, DMSO, water, and ionic liquid, 1-butyl-3-methylimidazolium tetrafluoroborate
Possible singlet oxygen generation from the photolysis of indigo dyes in methanol, DMSO, water, and ionic liquid, 1-butyl-3-methylimidazolium tetrafluoroborate
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DOI：
10.1016/j.tet.2006.08.095
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发表时间：
2006-11-13
期刊：
影响因子：
2.1
通讯作者：
Gao, Ruomei
中科院分区：
文献类型：
--
作者：
Gandra, Naveen;Frank, Aaron T.;Gao, Ruomei
我们认为，单重态分子氧[O-1(2)((1)Delta(G))]是由蓝1[在空气中或O-2饱和的二甲基亚MSO和二甲亚砜(0.5%H_2SO_4)]L和蓝胭脂红2[在空气或O-2饱和的CH_3OH、D_2O和1-丁基-3-甲基咪唑四氟硼酸盐(BmIm-BF_4)]照射下形成的。1的量子产率为0.6，2的量子产率为0.3-0.5。通过监测O-1(2)在1270 nm处的发射，确定了O-1(2)与1和2的反应速率。1和2的低摩尔吸光系数(532 Nm)和快速的物理猝灭限制了它们在溶液中作为O-1(2)光敏剂的应用。化合物I和2在光解过程中由于自身敏化(I类或II类)光氧化反应而缓慢降解。1被单线态氧和超氧化物氧化裂解，2被超氧化物氧化裂解已被注意到(Kuramoto，N.；Kitao，T.J.Soc.染料颜色。1999，95,257-261；Kettle，A.J.；Clark，B.M.；温特伯恩，C.C.J.Biol。化学。2004年、第279、18521-18525)。(C)2006爱思唯尔有限公司。保留所有权利。
We suggest that singlet molecular oxygen [O-1(2) ((1)Delta(g))] is formed upon irradiation of indigo 1 [in air or O-2-saturated DMSO and DMSO (0.5% H2SO4)l and indigo carmine 2 [in air or O-2-saturated CH3OH, D2O, and 1-butyl-3-methylimidazolium tetrafluoroborate (BmIm-BF4)]. The quantum yield for production Of 102 is estimated to be 0.6 for 1 and 0.3-0.5 for 2. The rates of reaction Of O-1(2) with 1 and 2 were determined by monitoring the emission Of O-1(2) at 1270 nm over time. Low molar absorptivities (at 532 nm) and rapid physical quenching caused by 1 and 2 limit their utility as O-1(2) photosensitizers in solution. Compounds I and 2 degrade slowly during the photolysis due to a self-sensitized (type I or II) photooxidation reaction. Oxidative cleavage of 1 by singlet oxygen and superoxide, and 2 by superoxide has been noted before (Kuramoto, N.; Kitao, T. J. Soc. Dyers Color. 1979,95,257-261; Kettle, A. J.; Clark, B. M.; Winterbourn, C. C. J. Biol. Chem. 2004, 279, 18521-18525). (c) 2006 Elsevier Ltd. All rights reserved.