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.