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4,5-Dimethylthio-4’-[2-(9-anthryloxy)ethylthio]tetrathiafulvalene, a Highly Selective and Sensitive Chemiluminescence Probe for Singlet Oxygen

Date: 09-24-2004   source: Huimin   Print

Xiaohua Li Guanxin Zhang Huimin Ma* Deqing Zhang* Jun Li and Daoben Zhu*

45-Dimethylthio-4’-[2-(9-anthryloxy)ethylthio]tetrathiafulvalene has been designed and synthesized as a highly selective and sensitive chemiluminescence (CL) probe for singlet oxygen (1O2). The design strategy for the probe is directed by the idea of photoinduced electron transfer process and carried out through the incorporation of electron-rich tetrathiafulvalene unit into a reactive luminophore of anthracene specific for 1O2. Upon reaction with reactive oxygen species (ROS) such as hydrogen peroxide hypochlorite superoxide hydroxyl radical or 1O2 the probe exhibits both strong CL response to and high selectivity for 1O2 only rather than the other ROS. This remarkable CL property permits 1O2 to be distinguished easily from the other ROS and makes the probe possible to be used widely for 1O2 detection in many chemical and biological systems and even in light water (H2O) environments. This applicability has been demonstrated by monitoring the 1O2 generation in a metal-catalyzed decomposition system of tert-butyl hydroperoxide. Moreover the CL reaction mechanism of the present system is also discussed clearly confirming that the introduction of electron-rich tetrathiafulvalene into the 9-position of anthracene can greatly activate its reactivity towards 1O2.

J. Am. Chem. Soc. 2004 126 11543-11548.

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