Ring Expansion of Spiro-thiolactam in Rhodamine Scaffold: Switching the Recognition Preference by Adding One Atom

作者：Cong Wu, Qing‐Na Bian, Bian-Guo Zhang, Xin Cai, Shudong Zhang, Hong Zheng, Shi‐Yao Yang, Yun‐Bao Jiang · 发表于：Organic Letters · 年份：2012 · DOI：10.1021/ol3018598 · 被引用次数：50 · 研究领域：Molecular Sensors and Ion Detection、Neuroscience and Neuropharmacology Research、Luminescence and Fluorescent Materials

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.