Abstract
We have studied the CdTe quantum dot-induced phototransformation of 2,4-dichlorophenol (2,4-DCP) and its subsequent chemiluminescence (CL) reaction. Quantum dots (QDs) of different size and capped with thioglycolic acid were prepared and characterized by molecular spectroscopy, X-ray diffraction and transmission electron microscopy. In the presence of QDs, 2,4-DCP is photochemically transformed into a long-living light emitting precursor which can react with N-bromosuccinimide to produce CL with peak wavelengths at 475 and 550 nm. The formation of singlet oxygen during the phototransformation process was confirmed by the enhancement effect of deuterium oxide on the CL reaction and the change in the UV spectrum of a chemical trap. The CL intensity is linearly related to the concentration of 2,4-DCP in the range from 0.36 to 36 μmol L−1, and the detection limit (at 3σ) is 0.13 μmol L−1.
Similar content being viewed by others
References
Smith AM, Nie SM (2004) Chemical analysis and cellular imaging with quantum dots. Analyst 129:672–677
Sapsford KE, Pons T, Medintz IL, Mattoussi H (2006) Biosensing with luminescent semiconductor quantum dots. Sensors 6:925–953
Chan WCW, Nie SM (1998) Quantum dot bioconjugates for ultrasensitive nonisotopic detection. Science 281:2016–2018
Bruchez MJ, Moronne M, Gin P, Weiss S, Alivisatos AP (1998) Semiconductor nanocrystals as fluorescent biological labels. Science 281:2013–2016
Coe S, Woo W, Bawendi M, Bulović V (2002) Electroluminescence from single monolayers of nanocrystals in molecular organic devices. Nature 420:800–803
Hansen JA, Wang J, Kawde A, Xiang Y, Gothelf KV, Gollins G (2006) Quantum-dot/aptamer-based ultrasensitive multi-analyte electrochemical biosensor. J Am Chem Soc 128:2228–2229
Ding ZF, Quinn BM, Haram SK, Pell LE, Korgel BA, Bard AJ (2002) Electrochemistry and electrogenerated chemiluminescence from silicon nanocrystal quantum dots. Science 296:1293–1297
Huang XY, Li L, Qian HF, Dong CQ, Ren JC (2006) A resonance energy transfer between chemiluminescence donors and luminescent quantum dots as acceptors (CRET). Angew Chem Int Ed 45:5140–5143
Wang ZP, Li J, Liu B, Hu JQ, Yao X, Li JH (2005) Chemiluminescence of CdTe nanocrystals induced by direct chemical oxidation and its size-dependent and surfactant-sensitized effect. J Phys Chem B 109:23304–23311
Guo JZ, Cui H (2007) Lucigenin chemiluminescence induced by noble metal nanoparticles in the presence of adsorbates. J Phys Chem C 111:12254–12259
Guo JZ, Cui H, Zhou W, Wang W (2008) Ag nanoparticle-catalyzed chemiluminescent reaction between luminol and hydrogen peroxide. J Photochem Photobiol A Chem 193:89–96
Li YX, Yang P, Wang P, Huang X, Wang L (2007) CdS nanocrystal induced chemiluminescence: reaction mechanism and applications. Nanotechnology 18:225602–225609
Li Z, Wang YX, Zhang GX, Xu WB, Han YJ (2010) Chemiluminescence resonance energy transfer in the luminol-CdTe quantum dots conjugates. J Lumin 130:995–999
Sun CY, Liu B, Li JH (2008) Sensitized chemiluminescence of CdTe quantum-dots on Ce(IV)-sulfite and its analytical applications. Talanta 75:447–454
Chen H, Lin L, Lin Z, Guo GS, Lin JM (2010) Chemiluminescence arising from the decomposition of peroxymonocarbonate and enhanced by CdTe quantum dots. J Phys Chem A 114:10049–10058
García-Campaňa AM, Baeyens WRG (2001) Chemiluminescence in analytical chemistry. Marcel Dekker, New York
Kanwal S, Fu XH, Su XG (2010) Size dependent active effect of CdTe quantum dots on pyrogallol-H2O2 chemiluminescence system for chromium (III) detection. Microchim Acta 169:167–172
Feng QZ, Li HF, Zhang ZY, Lin JM (2011) Gold nanoparticles for enhanced chemiluminescence and determination of 2,4-dichlorophenol in environmental water samples. Analyst 136:2156–2160
Li SF, Tao SJ, Wang FF, Hong JG, Wei XW (2010) Chemiluminescence reactions of luminol system catalyzed by nanoparticles of a gold/silver alloy. Microchim Acta 169:73–78
Albert-García JR, Icardo MC, Calatayud JM (2006) Analytical strategy photodegradation/chemiluminescence/continuous-flow multicommutation methodology for the determination of the herbicide propanil. Talanta 69:608–614
Palomeque M, García Bautista JA, Catalá Icardo M, García Mateo JV, Martínez Calatayud J (2004) Photochemical-chemiluminometric determination of aldicarb in a fully automated multicommutation based flow-assembly. Anal Chim Acta 512:149–156
Chivulescu A, Catalá-Icardo M, García Mateo JV, Martínez Calatayud J (2004) New flow-multicommutation method for the photo-chemiluminometric determination of the carbamate pesticide asulam. Anal Chim Acta 519:113–120
Song SJ, Song QJ, Chen ZL (2007) Online phototransformation-flow injection chemiluminescence determination of triclosan. Anal Bioanal Chem 387:2917–2922
Zhang JL, Song QJ, Hu X, Zhang EH, Gao H (2008) Dye–sensitized phototransformation of chlorophenols and their subsequent chemiluminescence reactions. J Lumin 128:1880–1885
Huang SS, Qu YX, Li RN, Shen J, Zhu LW (2008) Biosensor based on horseradish peroxide modified carbon nanotubes for determination of 2,4-dichlorophenol. Microchim Acta 162:261–268
Kong LM, Huang SS, Yue ZL, Peng B, Li MY, Zhang J (2009) Sensitive mediator-free tyrosinase biosensor for the determination of 2,4-dichlorophenol. Microchim Acta 165:203–209
Yaghini E, Seifalian AM, MacRobert AJ (2009) Quantum dots and their potential biomedical application in photosensitization for photodynamic therapy. Nanomedicine 4:353–363
Bang JH, Kamat PV (2009) Quantum dots sensitized solar cells. A tale of two semiconductor nanocrystals: CdSe and CdTe. ACS Nano 3:1467–1476
Nardello V, Azaroual N, Cervoise I, Vermeersch G, Aubry JM (1996) Synthesis and photooxidation of sodium 1,3-cyclohexadiene-1,4-diethanoate:a new colorless and water-soluble trap of singlet oxygen. Tetrahedron 52:2031–2046
Yu WW, Qu LH, Guo WZ, Peng XG (2003) Experimental determination of the extinction coefficient of CdTe, CdSe, and CdS nanocrystals. Chem Mater 15:2854–2860
Adam W, Kazakov DV, Kazakov VP (2005) Singlet-oxygen chemiluminescence in peroxide reactions. Chem Rev 105:3371–3387
Suzuki N, Takahashi A, Mashika S, Mizumoto I, Inaba H (1990) N, N’-dibromo-5,5-dimethylhydantoin and N-bromosuccinimide, chemical source of singlet molecular oxygen: observation of singlet oxygen with ultra-sensitive near-infraed chemiluminescence spectroscopy. Agric Biol Chem 54:459–462
Samia ACS, Chen XB, Burda C (2003) Semiconductor quantum dots for photodynamic therapy. J Am Chem Soc 125:15736–15737
Ma J, Chen JY, Zhang Y, Wang PN, Guo J, Yang WL, Wang CC (2007) Photochemical instability of thiol-capped CdTe quantum dots in aqueous solution and living cells: process and mechanism. J Phys Chem B 111:12012–12016
Cho SJ, Maysinger D, Jain M, Röder B, Hackbarth S, Winnik FM (2007) Long—term exposure to CdTe quantum dots causes functional impairments in live cells. Langmuir 23:1974–1980
Merkel PB, Nilsson R, Kearns DR (1972) Deuterium effects on singlet oxygen lifetimes in solutions. New test of singlet oxygen reactions. J Am Chem Soc 94:1030–1031
Liu JX, Chen H, Lin L, Lu C, Lin JM (2010) Sensitized chemiluminescence reaction between hydrogen peroxide and periodate of different types of Mn-doped ZnS quantum dots. Chin Sci Bull 55:3479–3484
Liu JX, Chen H, Lin Z, Lin JM (2010) Preparation of surface imprinting polymer capped Mn-doped ZnS quantum dots and their application for chemiluminescence detection of 4-nitrophenol in tap water. Anal Chem 82:7380–7386
Matsui J, Akamatsu K, Nishigushi S, Miyoshi D, Nawafune H, Tamaki K, Sugimoto N (2004) Composite of Au nanoparticles and molecularly imprinted polymer as a sensing material. Anal Chem 76:1310–1315
Acknowledgements
This work was supported financially by the National Natural Science Foundation of China (No. 20977042, 21175060), the Doctor Candidate Foundation of Jiangnan Unversity (No. JUDCF09009), the Rearing Fund for the Excellent Doctoral Dissertation of Jiangnan University.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
ESM 1
(DOC 32 kb)
Rights and permissions
About this article
Cite this article
Wu, H., Ding, Z., Peng, M. et al. Quantum dot induced phototransformation of 2,4-dichlorophenol, and its subsequent chemiluminescence reaction. Microchim Acta 178, 203–210 (2012). https://doi.org/10.1007/s00604-012-0830-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00604-012-0830-5