基于聚集诱导发光特性的荧光探针对汞离子的点亮型检测

doi:10.7517/j.issn.1674-0475.2016.06.513

影像科学与光化学 ›› 2016, Vol. 34 ›› Issue (6): 513-525.DOI: 10.7517/j.issn.1674-0475.2016.06.513

基于聚集诱导发光特性的荧光探针对汞离子的点亮型检测

潘小玲, 张亚会, 孔令伟, 石建兵, 佟斌, 董宇平

北京理工大学材料科学与工程学院北京市结构可控先进功能材料与绿色应用重点实验室, 北京 100081

收稿日期:2016-10-02 出版日期:2016-11-15 发布日期:2016-11-15
通讯作者: 石建兵, 董宇平
基金资助:
国家自然科学基金（973项目2013CB834704；51673024；21474009；51328302）资助

A “Turn-on” Fluorescent Chemosensor with the Aggregation-induced Emission Characteristic for High-selective Detection of Hg²⁺

PAN Xiaoling, ZHANG Yahui, KONG Lingwei, SHI Jianbing, TONG Bin, DONG Yuping

Beijing Key Laboratory of Construction Tailorable Advanced Functional Materials and Green Applications, School of Materials Science & Engineering, Beijing Institute of Technology, Beijing 100081, P. R. China

Received:2016-10-02 Online:2016-11-15 Published:2016-11-15

摘要/Abstract

摘要：

首先通过二溴六苯基丁二烯（HPB-Br）与4-乙烯基吡啶的Heck反应，获得含有两个吡啶基团的六苯基丁二烯（HPB-Py），再用碘甲烷甲基化得到含有双甲基吡啶碘盐的目标产物：六苯基-1，3-丁二烯衍生物（HPB-PyM）。作为HPB-PyM的前体化合物，HPB-Br和HPB-Py显示出优异的聚集诱导发光（AIE）特性。而HPB-PyM则呈现出聚集诱导猝灭（ACQ）特性，其固体呈橙红色荧光，发射波长λ_em=605 nm。当有汞离子存在的条件下，HPB-PyM基于AIE机制被点亮，并对Hg²⁺的检测具有响应速度快、灵敏度高和选择性强的特点，线性检测的最低限为4.153 μmol/L，证明HPB-PyM是一种新型“点亮”汞离子探针。

关键词: 六苯基-1,3-丁二烯衍生物, 高选择性, 检测汞离子, "点亮"荧光响应

Abstract:

A hexaphenyl-1,3-butadiene derivative containing methylpyridinium moiety, 4,4'-((1E,1'E)-(((1E,3E)-1,2,3,4-tetraphenylbuta-1,3-diene-1,4-diyl)bis(1,4-phenylene))bis(ethene-1,2-diyl))bis(N-methylpyridinium) iodide (HPB-PyM), was firstly synthesized through Heck reaction of HPB-Br with 4-vinylpyridine and subsequent methylation with iodomethane. As the precursors of HPB-PyM, HPB-Br and HPB-Py showed excellent aggregation-induced emission characteristic. In contrast, HPB-PyM exhibited orange emission (λ_em=605 nm) in the solid state with aggregation-caused quenching (ACQ) characteristic. Moreover, the fluorescence of HPB-PyM via AIE mechanism could be lightened and significantly enhanced by Hg²⁺ ions. As a "turn on" probe, HPB-PyM not only exhibited a rapid, sensitive, and selective response towards Hg²⁺ but also achieved linear and colorimetric detection for Hg²⁺ with a detection limit of 4.153 μmol/L.

Key words: hexaphenyl-1,3-butadiene derivative, high-selective, detection of Hg²⁺, "turn-on", fluorescent response

潘小玲, 张亚会, 孔令伟, 石建兵, 佟斌, 董宇平. 基于聚集诱导发光特性的荧光探针对汞离子的点亮型检测[J]. 影像科学与光化学, 2016, 34(6): 513-525.

PAN Xiaoling, ZHANG Yahui, KONG Lingwei, SHI Jianbing, TONG Bin, DONG Yuping. A “Turn-on” Fluorescent Chemosensor with the Aggregation-induced Emission Characteristic for High-selective Detection of Hg²⁺[J]. Imaging Science and Photochemistry, 2016, 34(6): 513-525.

参考文献

[1] Luo J, Xie Z, Lam J W Y, Cheng L, Chen H, Qiu C, Kwok H S, Zhan X, Liu Y, Zhu D, Tang B Z. Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole[J]. Chemical Communications, 2001,18(18):1740-1741.
[2] Shi X Y, Wang H, Han T Y, Feng X, Tong B, Shi J B, Zhi J G, Dong Y P. A highly sensitive, single selective, real-time and "turn-on" fluorescent sensor for Al³⁺ detection in aqueous media[J]. Journal of Materials Chemistry, 2012,22:19296-19302.
[3] Kong L W, Zhang Y H, Mao H L, Pan X L, Tian Y, Tian Z L, Zeng X K, Shi J B, Tong B, Dong Y P. Dimalononitrile-containing probe based on aggregation-enhanced emission feature for the multi-mode fluorescence detection of volatile amines[J]. Faraday Discussions, 2016, DOI:10.1039/C6FD00178E.
[4] Mei J, Leung N L, Kwok R T K, Lam J W Y, Tang B Z. Aggregation-induced emission-together we shine, united we soar[J]. Chemical Reviews, 2015,115:11718-11940.
[5] Valeur B, Leray I. Design principles of fluorescent molecular sensors for cation recognition[J]. Chemical Reviews, 2000,205(1):3-40.
[6] Kim H N, Ren W X, Kim J S, Yoon J. Fluorescent and colorimetric sensors for detection of lead, cadmium,and mercury ions[J]. Chemical Society Reviews, 2011,41(8):3210-3244.
[7] Fitzgerald W F, Lamborg C H, Hammerschmidt C R. Marine biogeochemical cycling of mercury[J]. Chemical Reviews, 2007, 107(2):641-662.
[8] Onyido I, Norris A R, Buncel E. Biomolecule-mercury interactions:modalities of DNA base-mercury binding mechanisms. remediation strategies[J]. Chemical Reviews, 2005,36(11):5911-5929.
[9] Henkel G, Krebs B. Metallothioneins:zinc, cadmium, mercury, and copper thiolates and selenolates mimicking protein active site features-structural aspects and biological implications[J]. Chemical Reviews, 2004,104(104):801-824.
[10] Nolan E M, Lippard S J. Tools and tactics for the optical detection of mercuric ion[J]. Chemical Reviews, 2008, 108(9):3443-3480.
[11] Tchounwou P B, Ayensu W K, Ninashvili N, Sutton D. Review:Environmental exposure to mercury and its toxicopathologic implications for public health[J]. Environmental Toxicology, 2003,18(3):149-175.
[12] Gong J, Zhou T, Song D, Zhang L, Hu X. Stripping voltammetric detection of mercury(Ⅱ) based on a bimetallic Au-Pt inorganic-organic hybrid nanocomposite modified glassy carbon electrode[J]. Analytical Chemistry, 2010,82(2):567-573.
[13] Anandhakumar S, Rajaram R, Mathiyarasu J. Unusual seedless approach to gold nanoparticle synthesis:application to selective rapid naked eye detection of mercury(Ⅱ)[J]. Analyst, 2014,139(13):3356-3359.
[14] Gu Z, Zhao M, Sheng Y, Bentolila L A, Tang Y. Detection of mercury ion by infrared fluorescent protein and its hydrogel-based paper assay[J]. Analytical Chemistry, 2011,83(6):2324-2329.
[15] DeSilva A P, Gunaratne H Q N, Gunnlaugsson T, Huxley A J M, McCoy C P, Rademacher J T, Rice T E. Signaling recognition events with fluorescent sensors and switches[J]. Chemical Reviews, 1997,97(5):1515-1566.
[16] Nolan E M, Lippard S J. Tools and tactics for the optical detection of mercuric ion[J]. Chemical Reviews, 2008,108(9):3443-3480.
[17] Coskun A, Yilmaz M D, Akkaya E U. Bis(2-pyridyl)-substituted boratriazaindacene as an NIR-emitting chemosensor for Hg(Ⅱ)[J]. Organic Letters, 2007,9(4):607-609.
[18] Bhalla V, Tejpal R, Kumar M, Sethi A. Terphenyl Derivatives as "turn on" fluorescent sensors for mercury[J]. Inorganic Chemistry, 2009,48(24):11677-11684.
[19] Kumar M, umar N, Bhalla V, Singh H, Sharma P R, Kaur T. Naphthalimide appended rhodamine derivative:through bond energy transfer for sensing of Hg²⁺ ions[J]. Organic Letters, 2011,13(6):1422-1425.
[20] Li C Y, Zhang X B, Qiao L, Zhao Y, He C M, Huan S Y, Lu L M, Jian L X, Shen G L, Yu R Q. Naphthalimide-porphyrin hybrid based ratiometric bioimaging probe for Hg²⁺:well-resolved emission spectra and unique specificity[J]. Analytical Chemistry, 2009,81(24):9993-10001.
[21] Hatai J, Pal S, Jose G P, Bandyopadhyay S. Histidine based fluorescence sensor detects Hg²⁺ in solution, paper strips, and in cells[J]. Inorganic Chemistry, 2012,51(19):10129-10135.
[22] Suresh M, Mandal A K, Saha S, Suresh E, Mandoli A, Liddo R D, Parnigotto P P, Das A. Azine-based receptor for recognition of Hg²⁺ ion:crystallographic evidence and imaging application in live cells[J]. Organic Letters, 2010,12(23):5406-5409.
[23] Srivastava P, Razi S S, Ali R, Gupta R C, Yadav S S, Narayan G, Misra A. Selective naked-eye detection of Hg²⁺ through an efficient turn-on photoinduced electron transfer fluorescent probe and its real applications[J]. Analytical Chemistry, 2014,86(17):8693-8699.
[24] Shellaiah M, Rajan Y C, Balu P, Murugan A. A pyrene based schiff base probe for selective fluore-scence turn-on detection of Hg²⁺ ions with live cell application[J]. New Journal of Chemistry, 2015,39:2523-2531.
[25] Chen C, Wang R, Guo L, Fu N, Dong H, Yuan Y. A squaraine-based colorimetric and "turn on" fluorescent sensor for selective detection of Hg²⁺ in an aqueous medium[J]. Organic Letters, 2011,13(5):1162-1165.
[26] Bera K, Das A K, Nag M, Basak S. Development of a rhodamine-rhodanine-based fluorescent mercury sensor and its use to monitor real-time uptake and distribution of inorganic mercury in live zebrafish larvae[J]. Analytical Chemistry, 2014,86(5):2740-2746.
[27] Zhou Y, Zhu C Y, Gao X S, You X Y, Yao C. Hg²⁺-selective ratiometric and "off-on" chemosensor based on the azadiene-pyrene derivative[J]. Organic Letters, 2010,12(11):2566-2569.
[28] Zhang Y H, Mao H L, Kong L W, Tian Y, Tian Z L, Zeng X K, Zhi J G, Shi J B, Tong B, Dong Y P. Effect of E-Z isomerization on the aggregation-induced emission features and mechanochromic performance[J]. Dyes and Pigments, 2016,133:354-362.

基于聚集诱导发光特性的荧光探针对汞离子的点亮型检测

A “Turn-on” Fluorescent Chemosensor with the Aggregation-induced Emission Characteristic for High-selective Detection of Hg²⁺

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基于聚集诱导发光特性的荧光探针对汞离子的点亮型检测

A “Turn-on” Fluorescent Chemosensor with the Aggregation-induced Emission Characteristic for High-selective Detection of Hg2+

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A “Turn-on” Fluorescent Chemosensor with the Aggregation-induced Emission Characteristic for High-selective Detection of Hg²⁺