Redox-controlled fluorescence modulation in a BODIPY-quinone dyad
Redox-controlled fluorescence modulation in a BODIPY-quinone dyad
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DOI：
10.1002/ejoc.200800191
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发表时间：
2008-06-01
影响因子：
2.8
通讯作者：
Clegg, William
中科院分区：
文献类型：
--
作者：
Benniston, Andrew C.;Copley, Graeme;Clegg, William
两个密切相关的硼二吡咯亚甲基（BODIPY）衍生的二联体，将氧化还原醌单元附加在meso位置的合成和性能进行了描述。对于一个二联体，醌单元直接连接到BODIPY核心，而亚苯基间隔子将第二化合物中的两个单元分开。每个醌单元通过化学和电化学方法容易地转化为相应的氢醌衍生物。通常与BODIPY单元相关的强荧光在两种二联体中以其醌形式有效地猝灭。这是由于第一激发单重态通过分子内电子转移过程失活。通过比较，观察到中等强度的荧光对苯二酚衍生物含有亚苯基间隔，但不是类似的直接耦合二分体。在生物膜模拟物中测试了亚苯基间隔的BODIPY醌和氢醌二联体对还原和氧化物质如抗坏血酸盐和过氧化物的潜在传感能力。在标准UV光激发下，荧光的可逆调制可以容易地通过眼睛检测。((c)Wiley-VCH Verlag GmbH & Co. KGaA，69451魏因海姆，德国，2008）。
The synthesis and properties of two closely related boron dipyrromethene (BODIPY) derived dyads, incorporating redoxactive quinone units appended at the meso position, are described. For one dyad, the quinone unit is attached directly to the BODIPY core, whereas a phenylene spacer separates the two units in the second compound. Each of the quinone units is readily converted, by both chemical and electrochemical means, to the corresponding hydroquinone derivative. The strong fluorescence normally associated with the BODIPY unit is efficiently quenched in both dyads in their quinone forms. This is attributed to deactivation of the first excited singlet state by a way of an intramolecular electron-transfer process. By comparison, moderately intense fluorescence is observed for the hydroquinone derivative containing the phenylene spacer, but not for the analogous directly coupled dyad. The potential sensing capabilities of the phenylene-spaced BODIPY quinone and hydroquinone dyads, towards reducing and oxidising species such as ascorbate and peroxide, were tested in a biomembrane mimic. A reversible modulation in fluorescence could be readily detected by eye under standard UV-Iight excitation. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).