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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Ring expansion of spiro-thiolactam in rhodamine scaffold: switching the recognition preference by adding one atom
Cong Wu1, Qing-Na Bian, Bian-Guo Zhang
1Department of Chemistry, College of Chemistry and Chemical Engineering, and the MOE Key Laboratory of Analytical Sciences, Xiamen University, Xiamen 361005, China.
Abstract:
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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