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  • Title: Ring expansion of spiro-thiolactam in rhodamine scaffold: switching the recognition preference by adding one atom.
    Author: Wu C, Bian QN, Zhang BG, Cai X, Zhang SD, Zheng H, Yang SY, Jiang YB.
    Journal: Org Lett; 2012 Aug 17; 14(16):4198-201. PubMed ID: 22870948.
    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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