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

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 chemo...

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Bibliographic Details
Published in:Organic letters 2012-08, Vol.14 (16), p.4198-4201
Main Authors: Wu, Cong, Bian, Qing-Na, Zhang, Bian-Guo, Cai, Xin, Zhang, Shu-Dong, Zheng, Hong, Yang, Shi-Yao, Jiang, Yun-Bao
Format: Article
Language:English
Subjects:
Copper - analysis
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Hydrazines - chemical synthesis
Hydrazines - chemistry
Mercury - analysis
Molecular Structure
Rhodamines - chemical synthesis
Rhodamines - chemistry
Spiro Compounds - chemistry
Water
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol3018598