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Syntheses and Ion Selectivities of Dimeric Rhodamine 6G Chemosensors

Chang, Seung Hyun;Choi, Jin-Wook;Chung, Kwang-Bo

  • Received : 2013.05.24
  • Accepted : 2013.10.21
  • Published : 2013.10.31

Abstract

Novel rhodamine 6G fluorescent chemosensors 1 and 2 for the detection of transition metal cations were synthesized through the condensation of rhodamine 6G ethylenediamine with each of 2-hydroxy-1-naphthaldehyde and 2,6-pyridinedicarbaldehyde, respectively. 1 and 2 were characterized using $^{13}C$ NMR, $^1H$ NMR and mass spectroscopy. Fluorometric and colorimetric measurements involving various metal ions revealed the ring opening of the rhodamine 6G spirocycle framework. In the absence of metal cations, 2 was colorless and non-fluorescent, whereas the addition of metal cations ($Hg^{2+}$ and others) changed the color to pink, accompanied by the appearance of an orange fluorescence. The chemosensors exhibited high selectivity for $Hg^{2+}$ over other divalent first-row transition metals. The complexes of $Hg^{2+}$ with 1 and 2 were successfully isolated. A huge enhancement in the fluorescence for both one- and two-photon excitations makes these compounds suitable candidates to be used for fluorescent labeling of biological systems.

Keywords

Rhodamine 6G;Fluorescent;Colorimetric;Chemosensor;Mercury

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