An Efficient Ag+-Selective Fluorescent Chemosensor Derived from Tribenzotriquinacene

Zhi-Min Li; Da Hu; Jun Wei; Qiuli Qi; Xiao-Ping Cao; Hak-Fun Chow; Dietmar Kuck

doi:10.1055/s-0036-1591759

Synthesis, Table of Contents

Synthesis 2018; 50(07): 1457-1461
DOI: 10.1055/s-0036-1591759

paper

An Efficient Ag⁺-Selective Fluorescent Chemosensor Derived from Tribenzotriquinacene

Authors

Zhi-Min Li

^aState Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, P. R. of China Email: caoxplzu@163.com
Da Hu

^aState Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, P. R. of China Email: caoxplzu@163.com
Jun Wei

^aState Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, P. R. of China Email: caoxplzu@163.com
Qiuli Qi

^bDepartment of Chemistry and Institute of Molecular Functional Materials, The Chinese University of Hong Kong, Shatin, Hong Kong, P. R. of China Email: hfchow@cuhk.edu.hk
Xiao-Ping Cao *

^aState Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, P. R. of China Email: caoxplzu@163.com
Hak-Fun Chow *

^bDepartment of Chemistry and Institute of Molecular Functional Materials, The Chinese University of Hong Kong, Shatin, Hong Kong, P. R. of China Email: hfchow@cuhk.edu.hk
Dietmar Kuck *

^cDepartment of Chemistry and Center for Molecular Materials (CM2), Bielefeld University, 33615 Bielefeld, Germany Email: dietmar.kuck@uni-bielefeld.de

Abstract

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Abstract

A new C _3v-symmetrical tribenzotriquinacene (TBTQ) derivative bearing six 8-quinolinyloxymethyl units at the rim of the bowl-shaped molecular framework is synthesized in a single-step by six-fold etherification of the corresponding hexakis(chloromethyl)-TBTQ precursor with 8-hydroxyquinoline. The resulting compound acts as a fluorescence chemosensor, producing a ‘turn-off’ fluorescent quenching response in the presence of Ag⁺ ions, and is highly selective toward Ag⁺ over other cations, such as Al³⁺, Ca²⁺, Cd²⁺, Co²⁺, Cr³⁺, Cu²⁺, Fe³⁺, Ga³⁺, Hg²⁺, In³⁺, K⁺, Mg²⁺, Mn²⁺, Na⁺, Ni²⁺, Pb²⁺, Pd²⁺, and Zn²⁺. The fluorescence intensity change of the chemosensor solution can be clearly observed by the naked eye upon addition of silver salts.

Key words

tribenzotriquinacenes - 8-quinolinyloxy derivatives - fluorescent chemosensors - chemoselectivity - silver ions

Full Text

References

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