Ring expansion of spiro-thiolactam in rhodamine scaffold: switching the recognition preference by adding one atom

Cong Wu, Qing-Na Bian, Bian-Guo Zhang, Xin Cai, Shu-Dong Zhang, Hong Zheng, Shi-Yao Yang, Yun-Bao Jiang
Organic Letters 2012 August 17, 14 (16): 4198-201
A new rhodamine spiro scaffold with a six-membered reactive ring was developed by inserting a nitrogen atom in the known probe rhodamine B spiro thiohydrazide, which switched the recognition preference of the probe from Hg(2+) to Cu(2+). This probe is shown to be an efficient "turn-on" fluorescent chemodosimeter for Cu(2+) in a neutral aqueous medium. Mechanism studies suggested that the probe opened its spiro-ring by a Cu(2+)-induced transformation of the cyclic thiosemicarbazide moiety to an isothiocyanate group.

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