Research Advance on the Fluorescent Probe of Palladium Ions

doi:10.11944/j.issn.1000-0518.2016.10.160238

Chinese Journal of Applied Chemistry ›› 2016, Vol. 33 ›› Issue (10): 1099-1114.DOI: 10.11944/j.issn.1000-0518.2016.10.160238

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Research Advance on the Fluorescent Probe of Palladium Ions

LI Haidong,YAO Qichao,FAN Jiangli,DU Jianjun,PENG Xiaojun()

State Key Laboratory of Fine Chemicals,Dalian University of Technology,Dalian,Liaoning 116024,China

Received:2016-06-06 Accepted:2016-07-14 Published:2016-10-08 Online:2016-10-08
Contact: PENG Xiaojun
Supported by:
Supported by the National Natural Science Foundation of China(No.21136002, No.21421005)

Abstract

Abstract:

A significant quantity of palladium is widely used in various materials, such as pharmacy, fuel cell, dental alloys and electronics, which inevitably cause its residues in the environment with pernicious effect on the body health. Therefore, it is of great significance to the detection and recognition of palladium. Owing to simple operation, high sensitivity, high sensitivity, low limit of detection, excellent high spatial and temporal resolution and especially nondestructive characteristics, fluorescent technique has been paid special attention. A variety of methods are discussed and introduced, which are applied in the design of fluorescent probes developed to detect the low concentration of palladium as well as mechanism of action in this review. Subsequently, the type of fluorescent probes mainly is classified into three kinds:quenching, turn-on and ratio based on response models. Although the molecular design of fluorescence probes of palladium has made an important progress, the response time of probes towards palladium is still uncontrollable. Additionally, it is not ideal for most fluorescent sensors to the detection of palladium in complex system. Developing rapid, high sensitive and selective fluorescent probes are suggested for future research to the detection of palladium ions in complex bio-system.

Key words: palladium, fluorescent probes, dyes, detection method, environment detection, drug residue, research advance, bio-imaging

LI Haidong,YAO Qichao,FAN Jiangli,DU Jianjun,PENG Xiaojun. Research Advance on the Fluorescent Probe of Palladium Ions[J]. Chinese Journal of Applied Chemistry, 2016, 33(10): 1099-1114.

References

[1]	Lesniewska B A,Godlewska-Zyłkiewicz B,Bocca B,et al.Platinum, Palladium and Rhodium Content in Road Dust, Tunnel Dust and Common Grass in Biaystok Area(Poland):A Pilot Study[J]. Sci Total Environ,2004,321(1/3):93-104.
[2]	Zischka M,Schramel P,Muntau H,et al.A New Certified Reference Material for the Quality Control of Palladium, Platinum and Rhodium in Road Dust[J]. Trends Anal Chem,2002,21(12):851-868.
[3]	Ravindra K,Bencs L,Van Grieken R.Platinum Group Elements in the Environment and Their Health Risk[J]. Sci Total Environ,2004,318(1/3):1-43.
[4]	Kielhorn J,Melber C,Keller D,et al.Palladium-A Review of Exposure and Effects to Human Health[J]. Int J Hyg Environ Health,2002,205(6):417-432.
[5]	CHANG Xijun,HUANG Yan,WANG Sui. Interaction Between Pd(Ⅱ) and Gamma Seroglobulinum Humanum[J]. Chinese J Anal Chem,2005,33(1):60-62(in Chinese). 常希俊,黄艳,王邃. 钯(Ⅱ)离子与人血丙种球蛋白的作用研究[J]. 分析化学,2005,33(1):60-62.
[6]	Ghosh A,Nandi S,Sengupta A,et al.Single Crystal X-ray Structurally Characterized Palladium(Ⅱ) Selective Fluorescence and Colorimetric Indicator for Human Breast Cancer Cell Imaging[J]. Inorg Chim Acta,2015,436:52-56.
[7]	Wang K,Lai G,Li Z,et al.A Novel Colorimetric and Fluorescent Probe for the Highly Selective and Sensitive Detection of Palladium Based on Pd(0) Mediated Reaction[J]. Tetrahedron,2015,71(41):7874-7878.
[8]	Wang P,Xia J,Gu Y.A Novel NIR Fluorescent Probe for Palladium Detection Based on Pd(0) Mediated Reaction[J]. Tetrahedron Lett,2015,56(46):6491-6494.
[9]	Chen Y,Chen B,Luo D,et al.A Facile Naphthalene-Based Fluorescent ‘Turn-On’ Chemodosimeter for Palladium Ions in Aqueous Solution[J]. Tetrahedron Lett,2016,57(10):1192-1195.
[10]	Qin J,Li X,Chen Z,et al.A Highly Selective and Commercially Available Fluorescence Probe for Palladium Detection[J]. Sens Actuators B Chem,2016,232:611-618.
[11]	Cui H,Chen H,Pan Y,et al.A Two-Photon Fluorescent Turn-On Probe for Palladium Imaging in Living Tissues[J]. Sens Actuators B Chem,2015,219:232-237.
[12]	Wang J Y,Liu Z R,Ren M,et al.A Fast-Responsive Two-Photon Fluorescent Probe for Detecting Palladium(0) with a Large Turn-On Fluorescence Signal[J]. J Photochem Photobiol A,2016,317:108-114.
[13]	Ali F,Taye N,Chattopadhyay S,et al.A New Turn On Pd2+-Specific Fluorescence Probe and Its Use as an Imaging Reagent for Cellular Uptake in Hct116 Cells[J]. Chem Commun,2015,51(17):3649-3652.
[14]	Chan J,Dodani S C,Chang C J.Reaction-Based Small-Molecule Fluorescent Probes for Chemoseletive Bioimaging[J]. Nature Chem,2012,4(12):973-984.
[15]	YU Haibo,LI Hongling,ZHANG Xinfu,et al.A Mitochondrial-Targetable and Turn-On Fluorescent Probe Based on Nile Red and Monitoring for H2S in Living Cells[J]. Acta Chim Sin,2015,73(5):450-456(in Chinese). 于海波,李红玲,张新富,等. 基于Nile Red的线粒体靶向性增强型硫化氢荧光探针及其细胞成像[J]. 化学学报,2015,73(5):450-456.
[16]	ZHANG Yong,LI Wei,WANG Qiang,et al.A Benzoxazole-Based Fluorescent Probe for Visual Detection of Hg2+[J]. Acta Chim Sin,2013,71(11):1496-1499(in Chinese). 张勇,李伟,王强,等. 一种基于苯并噁唑类的可视化检测汞离子的荧光探针[J]. 化学学报,2013,71(5):1496-1499.
[17]	CHEN Bin.Optical Probes Based on Coumarin and Rhoodamine Derivatives[D]. Dalian:State Key Laboratory of Fine Chemicals,Dalian University of Technology,2014(in Chinese). 陈斌. 基于香豆素及罗丹明的硫化氢及铜离子光学探针[D]. 大连:大连理工大学国家重点实验室,2014.
[18]	Zhang J F,Zhou Y,Yoon J Y,et al.Recent Progress in Fluorescent and Colorimetric Chemosensors for Detection of Precious Metal Ions(Silver, Gold and Platinum Ions)[J]. Chem Soc Rev,2011,40(7):3416-3429.
[19]	Li H D,Yao Q C,Fan J L,et al.A Fluorescent Probe for Ratiometric Imaging of SO2 Derivatives in Mitochondria of Living Cells[J]. Ind Eng Chem Res,2016,55(6):1477-1483.
[20]	TANG Kun,QIU Na,WU Pin,et al.Novel Water-Soluble Asymmetric Pentamethine Cyanine Dyes:Synthesis, Fluorescent Properties and Fluorescent Labeling[J]. Chinese J Appl Chem,2014,31(11):1255-1260(in Chinese). 汤昆,邱娜,吴品,等. 新型水溶性不对称五甲川吲哚菁染料的合成,荧光性能及荧光标记[J]. 应用化学,2014,31(11):1255-1260.
[21]	Tsien R Y.New Calcium Indicators and Buffers with High Selectivity Against Magnesium and Protons:Design, Synthesis, and Properties of Prototype Structures[J]. Biochemistry,1980,19(11):2396-2404.
[22]	YANG Zhigang,HE Yanxia,DAI Bin,et al.The Spectral Properties of Cy5 with Aldehyde Group Substituted at Meso-position of the Polymethine Chain Utilized as Fluorescent Viscosity Sensor[J]. Acta Chim Sin,2011,69(4):445-451(in Chinese). 杨志刚,和艳霞,戴彬,等. 中位醛基取代Cy5的光谱性能及作为粘度荧光探针的研究[J]. 化学学报,2011,69(4):445-451.
[23]	Ko S-K,Chen X Q,Yoon J Y,et al.Zebrafish as a Good Vertebrate Model for Molecular Imaging Using Fluorescent Probes[J]. Chem Soc Rev,2011,40(5):2120-2130.
[24]	YANG Tingting,GUO Zhiqian,SHAO Andong,et al.A Turn-On Fluorescent Probe for Cysteine Based on Benzopyran[J]. Chinese J Appl Chem,2016,33(4):397-405 (in Chinese). 杨婷婷,郭志前,邵安东,等. 基于苯并吡喃腈的激活型半胱氨酸荧光探针[J]. 应用化学,2016,33(4):397-405.
[25]	YUAN Yuehua,TIAN Maozhong,FENG Feng,et al.Rhodamine-Based Fluorescent Probes for Cations[J]. Prog Chem,2010,22(10):1929-1939(in Chinese). 袁跃华,田茂忠,冯峰,等. 罗丹明类阳离子荧光探针[J]. 化学进展,2010,22(10):1929-1939.
[26]	QIAO Bo.Rhodamine-Based Ratiometric Fluorescent Probe for the Determination of Pd2+ Ions[D]. Danlian:State Key Laboratory of Fine Chemicals,Dalian University of Technology,2014(in Chinese). 乔博. 基于罗丹明的比率型钯离子荧光探针研究[D]. 大连:大连理工大学精细化工国家重点实验室,2014.
[27]	Duan L P,Xu Y F,Qian X H.Highly Sensitive and Selective Pd2+ Sensor of Naphthalimide Derivative Based on Complexation with Alkynes and Thio-Heterocycle[J]. Chem Commun,2008,(47):6339-6341.
[28]	Hou J-T,Li K,Yu K K,et al.Novel Triazole-Based Fluorescent Probes for Pd2+ in Aqueous Solutions:Design, Theoretical Calculations and Imaging[J]. Analyst,2013,138(21):6632-6638.
[29]	Song F L,Garner A L,Koide K.A Highly Sensitive Fluorescent Sensor for Palladium Based on the Allylic Oxidative Insertion Mechanism[J]. J Am Chem Soc,2007,129(41):12354-12355.
[30]	Li H L,Fan J L,Du J J,et al.A Fluorescent and Colorimetric Probe Specific for Palladium Detection[J]. Chem Commun,2010,46(7):1079-1081.
[31]	Li H L,Fan J L,Hu M M,et al.Highly Sensitive and Fast-Responsive Fluorescent Chemosensor for Palladium:Reversible Sensing and Visible Recovery[J]. Chem-Eur J,2012,18(39):12242-12250.
[32]	Li H L,Cao J F,Zhu H,et al.Optical Pd2+ Sensing by Rhodamine Hydrazone Ligands:Different Stoichiometries in Aqueous/Nonaqueous Environments[J]. Tetrahedron Lett,2013,54(33):4357-4361.
[33]	Goswami S,Sen D,Das N K,et al.A New Rhodamine Based Colorimetric ‘Off-On’ Fluorescence Sensor Selective for Pd2+ Along with the First Bound X-ray Crystal Structure[J]. Chem Commun,2011,47(32):9101-9103.
[34]	Ren W X,Pradhan T,Yang Z,et al.Rapid Responsive Palladium Sensor under Mild Condition[J]. Sens Actuators B Chem,2012,171:1277-1282.
[35]	Keum D H,Kim S W,Kim Y M.A Fluorescence Turn-On Sensor for the Detection of Palladium Ions that Operates Through in Situ Generation of Palladium Nanoparticles[J]. Chem Commun,2014,50(10):1268-1270.
[36]	Yang M P,Bai Y J,Meng W F,et al.A Novel Selective Fluorescent and Colorimetric Chemosensor for the Visual Detection of Pd2+ and Application of Imaging in Living Cells[J]. Inorg Chem Commun,2014,46:310-314.
[37]	Chen Y,Zhang M,Han Y,et al.A Depropargylation-Triggered Spontaneous Cyclization Based Fluorescent “Turn-On” Chemodosimeter for the Detection of Palladium Ions and Its Application in Live-Cell Imaging[J]. RSC Adv,2016,6(10):8380-8383.
[38]	Chen X Q,Ying Z,Peng X J,et al.Fluorescent and Colorimetric Probes for Detection of Thiols[J]. Chem Soc Rev,2010,39(6):2120-2135.
[39]	Li H D,Yao Q C,Fan J L,et al.A Fluorescent Probe for H2S in Vivo with Fast Response and High Sensitivity[J]. Chem Commun,2015,51(90):16225-16228.
[40]	Jiang J,Jiang H,Liu W,et al.A Colorimetric and Ratiometric Fluorescent Probe for Palladium[J]. Org Lett,2011,13(18):4922-4925.
[41]	Chen H,Lin W Y,Yuan L.Construction of a Near-Infrared Fluorescence Turn-On and Ratiometric Probe for Imaging Palladium in Living Cells[J]. Org Biomol Chem,2013,11(12):1938-1941.
[42]	Cui L,Zhu W P,Xu Y F,et al.A Novel Ratiometric Sensor for the Fast Detection of Palladium Species with Large Red-Shift and High Resolution Both in Aqueous Solution and Solid State[J]. Anal Chim Acta,2013,786:139-145.
[43]	Wang J Y,Song F L,Wang J Y,et al.A Near-Infrared and Ratiometric Fluorescent Chemosensor for Palladium[J]. Analyst,2013,138(13):3667-3672.
[44]	Wang X H,Guo Z Q,Zhu S Q,et al.A Naked-Eye and Ratiometric Near-Infrared Probe for Palladium via Modulation of a π-Conjugated System of Cyanines[J]. Chem Commun,2014,50(88):13525-13528.
[45]	Sun S,Qiao B,Jiang N,et al.Naphthylamine-Rhodamine-Based Ratiometric Fluorescent Probe for the Determination of Pd2+[J]. Org Lett,2014,16(4):1132-1135.
[46]	Qiao B,Sun S,Jiang N,et al.A Ratiometric Fluorescent Probe for Determining Pd2+ Ions Based on Coordination[J]. Dalton Trans,2014,43(12):4626-4630.
[47]	Xiang K Q,Liu Y C,Li C J,et al.A Colorimetric and Ratiometric Fluorescent Probe for Detection of Palladium in the Red Light Region[J]. RSC Adv,2015,5(65):52516-52521.
[48]	Luo W F,Liu W S.A Two-Photon Ratiometric ESIPT Probe for the Discrimination of Different Palladium Species and Its Application in Bioimaging[J]. J Mater Chem B,2016,4(22):3911-3915.

Research Advance on the Fluorescent Probe of Palladium Ions

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