Discriminating detection of multiple analytes (F− and CN−) by a single probe through colorimetric and fluorescent dual channelsby Ying Wang, Qian Zhao, Libin Zang, Chunshuang Liang, Shimei Jiang

Dyes and Pigments

About

Year
2015
DOI
10.1016/j.dyepig.2015.07.039
Subject
Process Chemistry and Technology / Chemical Engineering (all)

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Text

Accepted Manuscript

Discriminating detection of multiple analytes (F‾ and CN‾) by a single probe through colorimetric and fluorescent dual channels

Ying Wang, Qian Zhao, Libin Zang, Chunshuang Liang, Shimei Jiang

PII: S0143-7208(15)00307-1

DOI: 10.1016/j.dyepig.2015.07.039

Reference: DYPI 4879

To appear in: Dyes and Pigments

Received Date: 29 April 2015

Revised Date: 27 July 2015

Accepted Date: 28 July 2015

Please cite this article as: Wang Y, Zhao Q, Zang L, Liang C, Jiang S, Discriminating detection of multiple analytes (F‾ and CN‾) by a single probe through colorimetric and fluorescent dual channels,

Dyes and Pigments (2015), doi: 10.1016/j.dyepig.2015.07.039.

This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.

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ACCEPTED MANUSCRIPT

Discriminating detection of multiple analytes (F‾ and

CN‾) by a single probe through colorimetric and fluorescent dual channels

Ying Wang,a,b Qian Zhao,a Libin Zang,a Chunshuang Lianga and Shimei Jiang*a

A new “one to more” type sensor has been developed for the selective and discriminating detection towards F‾ and CN‾ through the colorimetric and fluorescent channels, which was based on the different mechanisms for the two anions.

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ACCEPTED MANUSCRIPT 1

Discriminating detection of multiple analytes (F‾ and CN‾) by a single probe through colorimetric and fluorescent dual channels

Ying Wang,a,b Qian Zhao,a Libin Zang,a Chunshuang Lianga and Shimei Jiang*a aState Key Laboratory of Supramolecular Structure and Materials, Jilin University, 2699

Qianjin Avenue, Changchun 130012, P. R. China. bHeilongjiang Key Laboratory of Molecular Design and Preparation of Flame Retarded

Materials, College of Science, Northeast Forestry University, Harbin 150040, P. R. China. *Corresponding author: Shimei Jiang

E-mail: smjiang@jlu.edu.cn

Tel: +86-431-85168474

Fax: +86-431-85193421

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Abstract:

Two novel Schiff base type receptors containing phenol hydroxyl group (1) or methoxy group (2) were designed and synthesized. The receptor 1 with phenol hydroxyl group exhibited different colorimetric and fluorimetric responses to fluoride and cyanide ions. In the colorimetric channel, the colorless solution turned to yellow towards F‾, but red in the presence of CN‾. In the fluorimetric channel, the nonluminous solution showed different “turn-on” response to F‾ and CN‾, respectively. The distinguishing responses of receptor 1 to the two anions in dual channels were attributed to the disparate interaction mechanisms. F‾ was detected through the formation of hydrogen bonds and the subsequent deprotonation process.

CN‾ initially formed hydrogen bonds and then it attacked the receptor via a nucleophilic addition reaction. In contrast, the receptor 2 with methoxy group only showed remarkable color change from colorless to yellow towards F‾. These results proved that the phenol hydroxyl group played an important role in the discriminating detection of F‾ and CN‾.

Keywords: colorimetric and fluorescent probe, Schiff base, fluoride, cyanide.

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ACCEPTED MANUSCRIPT 3 1. Introduction

Among various anions, fluoride and cyanide ions are numerous indispensable in chemical, biological, clinical, environmental, and industrial fields [1]. Fluoride ion is in close contact with human’s daily life such as water supply treatment, osteoporosis treatment, dental care and even in chemical warfare agents. However, high doses of fluoride ions is hazardous, which can led to nephrolithiasis, kidney failure and dentalor skeletal fluorosis [2]. On the other hand, cyanide ion extraordinarily ubiquitous in many industrial processes is one of the most prevalent toxic anions to mammals, because a small amount of cyanide can cause vomiting, convulsions, loss of consciousness, and even death [3]. Therefore, the development of convenient and efficient detection techniques for fluoride and cyanide ions has drawn great attention in recent years. Compared with the traditional sophisticated analytical techniques, optical chemosensors that rely on fluorometric and colorimetric responses are simple, inexpensive and rapid methods [4]. Especially, “naked-eye” optical sensors are extremely dramatic [5].

More recently, “one to more” type sensors that can recognize two or more target analytes with distinct responses independently, have already become a new research focus [6]. Compared with most single-ion responsive chemosensors, they have advantages like faster analytical processing, cost reductions and potential application to molecular logic gates [7].

During the past years, the optical sensors for detecting either F‾ or CN‾ have been extensively exploited [8]. As the most electronegative atom, fluoride can form strong hydrogen bonds with some hydrogen bond donors. Thus, various chemosensors

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ACCEPTED MANUSCRIPT 4 containing acidic NH and OH groups have been developed to detect fluoride [9a, 9b].

On the other hand, some fluorescent sensors containing tert-butyldimethylsilyl (TBDMS) or tert-butyldiphenylsilyl (TBDPS) groups that are capable of detecting fluoride ions in water have been reported. The sensing strategy resulted from the chemical affinity between fluoride and silicon (fluoride-mediated cleavage of Si-O bond), enabling the probe molecule unreactive to potentially interfering anions and thus only sensitive to fluoride ions. Since such approach was first reported by Kim and Swager, several different chemosensors or probes that can detect NaF in aqueous media have been developed [9c, 9d]. Meanwhile, the detection of cyanide has been achieved through various approaches such as the formation of hydrogen bond [10], deprotonation process [11], chemodosimeters [12], and displaycement method [13].