Ring Expansion of Spiro-thiolactam in Rhodamine Scaffold: Switching the Recognition Preference by Adding One Atom
2012
Wu, Cong | Bian, Qing-Na | Zhang, Bian-Guo | Cai, Xin | Zhang, Shu-Dong | Zheng, Hong | Yang, Shi-Yao | Jiang, Yun-Bao
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 Hg²⁺ to Cu²⁺. This probe is shown to be an efficient “turn-on” fluorescent chemodosimeter for Cu²⁺ in a neutral aqueous medium. Mechanism studies suggested that the probe opened its spiro-ring by a Cu²⁺-induced transformation of the cyclic thiosemicarbazide moiety to an isothiocyanate group.
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