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Issue 7, 2009
From the journal:

Organic & Biomolecular Chemistry

A red-shift colorimetric and fluorescent sensor for Cu2+ in aqueous solution: unsymmetrical 4,5-diaminonaphthalimide with N-H deprotonation induced by metal ions†

Junhai Huang,a   Yufang Xua  and  Xuhong Qian*a  

* Corresponding authors

a Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai, China
E-mail: xhqian@ecust.edu.cn
Fax: +86 21 64252603
Tel: +86 21 64253589

Abstract

4,5-Diamino-1,8-naphthalimide (DNP)-based chemosensor H1 was designed and synthesized. Probe H1 specifically recognized Cu2+ ions in neutral aqueous solution. The capture of Cu2+ by the receptor resulted in deprotonation of the secondary amine conjugated to the 1,8-naphthalimide chromophore, so that the electron-donation ability of the “N” atom would be greatly enhanced; thus probe H1 showed a 50 nm red-shift in absorption (from 464 nm to 514 nm) and a large colorimetric response, it also exhibited an on-off fluorescent response. Specifically, H1 is a pH-independent sensor in the range of 6.0 to 12.0 and can be used as a probe for Cu2+ in strong basic conditions. These results opened up new possibilities for construction of red-shift colorimetric and fluorescent sensors.

Graphical abstract: A red-shift colorimetric and fluorescent sensor for Cu2+ in aqueous solution: unsymmetrical 4,5-diaminonaphthalimide with N-H deprotonation induced by metal ions

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Article information

DOI
https://doi.org/10.1039/B818611A
Article type
Paper
Submitted
21 Oct 2008
Accepted
26 Nov 2008
First published
10 Feb 2009

Org. Biomol. Chem., 2009,7, 1299-1303

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A red-shift colorimetric and fluorescent sensor for Cu2+ in aqueous solution: unsymmetrical 4,5-diaminonaphthalimide with N-H deprotonation induced by metal ions

J. Huang, Y. Xu and X. Qian, Org. Biomol. Chem., 2009, 7, 1299 DOI: 10.1039/B818611A

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