Abstract
Carbon dots doped with nitrogen and copper have been synthesized via a hydrothermal method. They possess favorable peroxidase-like catalytic activity over a wide range of pH values and temperatures. Specifically, they were used to catalyze the oxidation of ortho- and para-phenylenediamine (OPD and PPD) by H2O2. The resulting products possess different colors (yellow for OPD and brown for PPD), which can be visually discriminated. The corresponding typical absorption peaks of oxidized products for OPD and PPD are at 413 nm and 500 nm, respectively. The method displays excellent discrimination ability and selectivity over potential interferents. The detection limits are 1.1 μM for OPD and 1.9 μM for PPD. The respective linear ranges are from 5 to 200 μM for OPD and from 2.5 to 700 μM for PPD. The method was applied to the quantification of OPD and PPD in spiked natural waters.
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References
Yan ZY, Yu Y, Chen JQ (2015) Glycine-functionalized carbon quantum dots as chemiluminescence sensitization for detection of m-phenylenediamine. Anal Methods 7(3):1133–1139
Li N, Gu Y, Gao MM, Wang ZL, Xiao DL, Li Y, Lin R, He H (2015) Colorimetric determination of o-phenylenediamine in water samples based on the formation of silver nanoparticles as a colorimetric probe. Spectrochim Acta A 140:328–333
Ngamdee K, Martwiset S, Tuntulani T, Ngeontae W (2012) Selective fluorescence sensors for p-phenylenediamine using formyl boronate ester with an assistance of micelles. Sensors Actuators B Chem 173:682–691
Nezamzadeh-Ejhieh A, Salimi Z (2010) Heterogeneous photodegradation catalysis of o-phenylenediamine using CuO/X zeolite. Appl Catal A Gen 390(1–2):110–118
Lee SJ, Nam YS, Nah IW, Lee YH, Lee KB (2017) Colorimetric determination of p-phenylenediamine using silver nanoparticles modified with poly (ethylene glycol) methyl ether thiol. J Nanosci Nanotechnol 17(5):3261–3267
Ma PY, Liang FH, Wang D, Yang QQ, Cao BC, Song DQ, Gao DJ, Wang XH (2014) Selective determination of o-phenylenediamine by surface-enhanced Raman spectroscopy using silver nanoparticles decorated with α-cyclodextrin. Microchim Acta 182(1–2):167–174
Dong SQ, Chi LZ, Zhang S, He PG, Wang QJ, Fang YZ (2008) Simultaneous determination of phenylenediamine isomers and dihydroxybenzene isomers in hair dyes by capillary zone electrophoresis coupled with amperometric detection. Anal Bioanal Chem 391(2):653–659
Hudari FF, Almeida LC, Silva BF, Zanoni MVB (2014) Voltammetric sensor for simultaneous determination of p-phenylenediamine and resorcinol in permanent hair dyeing and tap water by composite carbon nanotubes/chitosan modified electrode. Microchem J 116:261–268
Guo DD, Lou CY, Wang NN, Chen ML, Zhang PM, Wu SC, Zhu Y (2017) Poly (styrene-divinyl benzene-glycidylmethacrylate) stationary phase grafted with poly amidoamine (PAMAM) dendrimers for rapid determination of phenylene diamine isomers in HPLC. Talanta 168:188–195
Shi BF, Su YB, Zhang LL, Huang MJ, Li XF, Zhao SL (2016) Facilely prepared Fe3O4/nitrogen-doped graphene quantum dot hybrids as a robust nonenzymatic catalyst for visual discrimination of phenylenediamine isomers. Nanoscale 8(20):10814–10822
Maria-Hormigos R, Jurado-Sanchez B, Escarpa A (2018) Self-propelled micromotors for naked-eye detection of phenylenediamines isomers. Anal Chem 90(16):9830–9837
Sun HJ, Zhou Y, Ren JS, Qu XG (2018) Carbon nanozymes: enzymatic properties, catalytic mechanism, and applications. Angew Chem Int Ed 57(30):9224–9237
Xie JX, Zhang XD, Wang H, Zheng HZ, Huang YM, Xie JX (2012) Analytical and environmental applications of nanoparticles as enzyme mimetics. TrAC Trend Anal Chem 39:114–129
Nasir M, Nawaz MH, Yaqub M, Hayat A, Rahim A (2017) An overview on enzyme-mimicking nanomaterials for use in electrochemical and optical assays. Microchim Acta 184(2):323–342
Lin LP, Song XH, Chen YY, Rong MC, Zhao TT, Wang YR, Chen X (2015) Intrinsic peroxidase-like catalytic activity of nitrogen-doped graphene quantum dots and their application in the colorimetric detection of H2O2 and glucose. Anal Chim Acta 869:89–95
Liao H, Liu GJ, Liu Y, Li R, Fu WS, Hu LZ (2017) Aggregation-induced accelerating peroxidase-like activity of gold nanoclusters and their applications for colorimetric Pb2+ detection. Chem Commun 53:10160–10163
Liao H, Hu LZ, Zhang YZ, Yu XR, Liu YL, Li R (2018) A highly selective colorimetric sulfide assay based on the inhibition of the peroxidase-like activity of copper nanoclusters. Microchim Acta 185:143
Hu LZ, Liao H, Feng LY, Wang M, Fu WS (2018) Accelerating the peroxidase-like activity of gold nanoclusters at neutral pH for colorimetric detection of heparin and heparinase activity. Anal Chem 90(10):6247–6252
Liu HM, Wang BC, Li DH, Zeng XY, Tang X, Gao QS, Cai JY, Cai HH (2018) MoS2 nanosheets with peroxidase mimicking activity as viable dual-mode optical probes for determination and imaging of intracellular hydrogen peroxide. Microchim Acta 185(6):287
Tran HV, Nguyen TV, Nguyen ND, Piro B, Huynh CD (2018) A nanocomposite prepared from FeOOH and N-doped carbon nanosheets as a peroxidase mimic, and its application to enzymatic sensing of glucose in human urine. Microchim Acta 185:270
Tang S, Wang M, Li G, Li X, Chen W, Zhang L (2018) Ultrasensitive colorimetric determination of silver(I) based on the peroxidase mimicking activity of a hybrid material composed of graphitic carbon nitride and platinum nanoparticles. Microchim Acta 185(5):273
Lin LP, Luo YX, Tsai PY, Chen X (2018) Metal ions doped carbon quantum dots: synthesis, physicochemical properties, and their applications. TrAC Trend Anal Chem 103:87–101
Huang HW, Liu LF, Zhang LY, Zhao Q, Zhou Y, Yuan SS, Tang ZL, Liu XY (2017) Peroxidase-like activity of ethylene diamine tetraacetic acid and its application for ultrasensitive detection of tumor biomarkers and circular tumor cells. Anal Chem 89(1):666–672
Ren XL, Liu J, Ren J, Tang FQ, Meng XW (2015) One-pot synthesis of active copper-containing carbon dots with laccase-like activities. Nanoscale 7(46):19641–19646
Durán GM, Benavidez TE, Contento AM, Ríos A, García CD (2017) Analysis of penicillamine using Cu-modified graphene quantum dots synthesized from uric acid as single precursor. J Pharm Anal 7(5):324–331
Xia JB, Yuan SW, Wang Z, Kirklin S, Dorney B, Liu DJ, Yu LP (2010) Nanoporous polyporphyrin as adsorbent for hydrogen storage. Macromolecules 43(7):3325–3330
Wu WT, Zhan LT, Fan WY, Song JZ, Li XM, Li ZT, Wang RQ, Zhang JQ, Zheng JT, Wu MB, Zeng HB (2015) Cu-N dopants boost electron transfer and photooxidation reactions of carbon dots. Angew Chem Int Ed 54(22):6540–6544
Ma YS, Cen Y, Sohail M, Xu GH, Wei FD, Shi ML, Xu XM, Song YY, Ma YJ, Hu Q (2017) A ratiometric fluorescence universal platform based on N, Cu codoped carbon dots to detect metabolites participating in H2O2-generation reactions. ACS Appl Mater Interfaces 9(38):33011–33019
Bao YW, Hua XW, Li YH, Jia HR, Wu FG (2018) Hyperthemia-promoted cytosolic and nuclear delivery of copper/carbon quantum dot-crosslinked nanosheets: multimodal imaging-guided photothermal cancer therapy. ACS Appl Mater Interfaces 10(2):1544–1555
Guldi DM, Rahman GM, Jux N, Balbinot D, Hartnagel U, Tagmatarchis N, Prato M (2005) Functional single-wall carbon nanotube nanohybrids associating SWNTs with water-soluble enzyme model systems. J Am Chem Soc 127(27):9830–9838
Luque GL, Rojas MI, Rivas GA, Leiva EPM (2010) The origin of the catalysis of hydrogen peroxide reduction by functionalized graphene surfaces: a density functional theory study. Electrochim Acta 56(1):523–530
Tang YF, Allen BL, Kauffman DR, Star A (2009) Electrocatalytic activity of nitrogen-doped carbon nanotube cups. J Am Chem Soc 131(37):13200–13201
Fornera S, Yazawa K, Walde P (2011) Spectrophotometric quantification of lactose in solution with a peroxidase-based enzymatic cascade reaction system. Anal Bioanal Chem 401:2307–2310
Khattar R, Yadav A, Mathur P (2015) Copper (II) complexes as catalyst for the aerobic oxidation of o-phenylenediamine to 2, 3-diaminophenazine. Spectrochim Acta A 142:375–381
Acknowledgments
This research work was financially supported by Nature Science Foundation from Science and Technology Department of Fujian Province (No. 2018J05013), Education Research Project for Young and Middle-aged Teachers of Fujian Province (No. JT180136), Outstanding Youth Research Training Program of Fujian Agriculture and Forestry University (xjq201818) and National Natural Science Foundation of China (No. 21876141), which are gratefully acknowledged.
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Lin, L., Xiao, Y., Wang, Y. et al. Hydrothermal synthesis of nitrogen and copper co-doped carbon dots with intrinsic peroxidase-like activity for colorimetric discrimination of phenylenediamine isomers. Microchim Acta 186, 288 (2019). https://doi.org/10.1007/s00604-019-3404-y
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DOI: https://doi.org/10.1007/s00604-019-3404-y