Ratiometric fluorescent and colorimetric sensors for Cu2+ based on 4,5-disubstituted-1,8-naphthalimide and sensing cyanide via Cu2+ displacement approach

Zhaochao Xu; Jie Pan; David R. Spring; Jingnan Cui; Juyoung Yoon

doi:10.1016/j.tet.2010.01.008

Ratiometric fluorescent and colorimetric sensors for Cu²⁺ based on 4,5-disubstituted-1,8-naphthalimide and sensing cyanide via Cu²⁺ displacement approach

Zhaochao Xu, Jie Pan, David R. Spring, Jingnan Cui, Juyoung Yoon

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

177 Scopus citations

Abstract

Two 4,5-disubstituted-1,8-naphthalimide derivatives 1 and 2 were synthesized as ratiometric fluorescent and colorimetric sensors for Cu²⁺, respectively. In 100% aqueous solutions of 1, the presence of Cu²⁺ induces a strong and increasing fluorescent emission centered at 478 nm at the expense of the fluorescent emission of 1 centered at 534 nm. Compound 2 senses Cu²⁺ by means of a colorimetric (primrose yellow to pink) method with a thorough quench in emission attributed to the deprotonation of the secondary amine conjugated to the naphthalimide fluorophore. 1-Cu²⁺ and 2-Cu²⁺ sense cyanide in ratiometric way via colorimetric and fluorescent changes.

Original language	English
Pages (from-to)	1678-1683
Number of pages	6
Journal	Tetrahedron
Volume	66
Issue number	9
DOIs	https://doi.org/10.1016/j.tet.2010.01.008
State	Published - 27 Feb 2010

Bibliographical note

Funding Information:
This work was supported by Basic Science Research Program ( 20090083065 ) and the Converging Research Center Program ( 2009-0093677 ) through the National Research Foundation of Korea ( NRF ) funded by the Ministry of Education, Science and Technology, and State Key Laboratory of Fine Chemicals of China ( KF0809 ).

Keywords

Colorimetric
Cu
Cyanide
Fluorescent
Naphthalimide
Ratiometric

Access to Document

10.1016/j.tet.2010.01.008

Cite this

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title = "Ratiometric fluorescent and colorimetric sensors for Cu2+ based on 4,5-disubstituted-1,8-naphthalimide and sensing cyanide via Cu2+ displacement approach",

abstract = "Two 4,5-disubstituted-1,8-naphthalimide derivatives 1 and 2 were synthesized as ratiometric fluorescent and colorimetric sensors for Cu2+, respectively. In 100% aqueous solutions of 1, the presence of Cu2+ induces a strong and increasing fluorescent emission centered at 478 nm at the expense of the fluorescent emission of 1 centered at 534 nm. Compound 2 senses Cu2+ by means of a colorimetric (primrose yellow to pink) method with a thorough quench in emission attributed to the deprotonation of the secondary amine conjugated to the naphthalimide fluorophore. 1-Cu2+ and 2-Cu2+ sense cyanide in ratiometric way via colorimetric and fluorescent changes.",

keywords = "Colorimetric, Cu, Cyanide, Fluorescent, Naphthalimide, Ratiometric",

author = "Zhaochao Xu and Jie Pan and Spring, {David R.} and Jingnan Cui and Juyoung Yoon",

note = "Funding Information: This work was supported by Basic Science Research Program ( 20090083065 ) and the Converging Research Center Program ( 2009-0093677 ) through the National Research Foundation of Korea ( NRF ) funded by the Ministry of Education, Science and Technology, and State Key Laboratory of Fine Chemicals of China ( KF0809 ). ",

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language = "English",

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T1 - Ratiometric fluorescent and colorimetric sensors for Cu2+ based on 4,5-disubstituted-1,8-naphthalimide and sensing cyanide via Cu2+ displacement approach

AU - Xu, Zhaochao

AU - Pan, Jie

AU - Spring, David R.

AU - Cui, Jingnan

AU - Yoon, Juyoung

N1 - Funding Information: This work was supported by Basic Science Research Program ( 20090083065 ) and the Converging Research Center Program ( 2009-0093677 ) through the National Research Foundation of Korea ( NRF ) funded by the Ministry of Education, Science and Technology, and State Key Laboratory of Fine Chemicals of China ( KF0809 ).

PY - 2010/2/27

Y1 - 2010/2/27

N2 - Two 4,5-disubstituted-1,8-naphthalimide derivatives 1 and 2 were synthesized as ratiometric fluorescent and colorimetric sensors for Cu2+, respectively. In 100% aqueous solutions of 1, the presence of Cu2+ induces a strong and increasing fluorescent emission centered at 478 nm at the expense of the fluorescent emission of 1 centered at 534 nm. Compound 2 senses Cu2+ by means of a colorimetric (primrose yellow to pink) method with a thorough quench in emission attributed to the deprotonation of the secondary amine conjugated to the naphthalimide fluorophore. 1-Cu2+ and 2-Cu2+ sense cyanide in ratiometric way via colorimetric and fluorescent changes.

AB - Two 4,5-disubstituted-1,8-naphthalimide derivatives 1 and 2 were synthesized as ratiometric fluorescent and colorimetric sensors for Cu2+, respectively. In 100% aqueous solutions of 1, the presence of Cu2+ induces a strong and increasing fluorescent emission centered at 478 nm at the expense of the fluorescent emission of 1 centered at 534 nm. Compound 2 senses Cu2+ by means of a colorimetric (primrose yellow to pink) method with a thorough quench in emission attributed to the deprotonation of the secondary amine conjugated to the naphthalimide fluorophore. 1-Cu2+ and 2-Cu2+ sense cyanide in ratiometric way via colorimetric and fluorescent changes.

KW - Colorimetric

KW - Cu

KW - Cyanide

KW - Fluorescent

KW - Naphthalimide

KW - Ratiometric

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