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Issue 24, 2011
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Bis- and tris-naphthoimidazolium derivatives for the fluorescent recognition of ATP and GTP in 100% aqueous solution†

Zhaochao Xu,‡ac   Na Ri Song,‡b   Jong Hun Moon,‡d   Jin Yong Lee*d  and  Juyoung Yoon*ab  
Author affiliations

* Corresponding authors

a Department of Chemistry and Nano Science, Ewha Womans University, Seoul 120-750, Korea
E-mail: jyoon@ewha.ac.kr
Fax: (+82) 2-3277-2384

b Department of Bioinspired Science, Ewha Womans University, Seoul 120-750, Korea

c Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China

d Department of Chemistry, Sungkyunkwan University, Suwon 440-746, Korea
E-mail: jinylee@skku.edu

Abstract

Naphthoimidazolium groups can form unique ionic hydrogen bonds with anions as imidazolium moieties, and in addition, they are fluorescent, so no further elaborative synthesis is needed to introduce a fluorescent group. In this paper, three naphthoimidazolium derivatives were synthesized and studied for the recognition of nucleotides. Compound 1 composed of a single naphthoimidazolium group and quaternary ammonium group did not show any significant fluorescent changes with various anions and nucleotides, such as ATP, GTP, CTP, TTP, UTP, ADP and AMP. A tripodal compound 3 bearing three naphthoimidazolium groups and three quaternary ammonium groups, respectively, showed large fluorescence enhancements with UTP, CTP and TTP and moderate fluorescence enhancements with ATP and pyrophosphate and a fluorescence quenching effect with GTP. On the other hand, compound 2 bearing two naphthoimidazolium groups and two quaternary ammonium groups displayed a selective fluorescence enhancement with ATP and a selective fluorescence quenching effect with GTP in 100% aqueous solution.

Graphical abstract: Bis- and tris-naphthoimidazolium derivatives for the fluorescent recognition of ATP and GTP in 100% aqueous solution

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Supplementary files

Article information

Submitted
08 Aug 2011
Accepted
19 Sep 2011
First published
19 Sep 2011
Org. Biomol. Chem., 2011,9, 8340-8345
Article type
Paper
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Bis- and tris-naphthoimidazolium derivatives for the fluorescent recognition of ATP and GTP in 100% aqueous solution

Z. Xu, N. R. Song, J. H. Moon, J. Y. Lee and J. Yoon, Org. Biomol. Chem., 2011, 9, 8340
DOI: 10.1039/C1OB06344H

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