Skip to main content
Log in

Fluorescent Carbon Dots as Cost-Effective and Facile Probes for Caffeic Acid Sensing via a Fluorescence Quenching Process

  • ORIGINAL ARTICLE
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

Caffeic acid (CA), a familiar color stabilizing reagent, has aroused general concern due to its uncontrolled addition, and thus the detection of CA is increasingly important. In our report, the bright carbon dots (CDs) were prepared via hydrothermal treatment with urea and citric acid act as raw material and their characteristics were discussed through X-ray diffraction (XRD), transmission electron microscopy (TEM) and so on. Impressively, the strong emission of the as-prepared CDs (Quantum Yield: 24.3%) decreased sharply upon a full reaction with the added CA. Hence, we first present an improved strategy for determining CA based upon the quenching of the strong emission of CDs. In this strategy, 0.79–100.0 µmol L− 1 caffeic acid could be simply detected, and a detection limit of 0.24 µmol L− 1 was allowed. Additionally, CA in red wine samples can be successfully detected by this method and the exploration of the quenching mechanism of the CA-CDs system was done.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Scheme 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Silberberg M, Morand C, Mathevon T, Besson C, Manach C, Scalbert A, Remesy C (2006) The bioavailability of polyphenols is highly governed by the capacity of the intestine and of the liver to secrete conjugated metabolites. Eur J Nutr 45:88–96

    Article  PubMed  CAS  Google Scholar 

  2. Abu-amsha R, Croft KD, Puddey IB, Proudfoot JM, Beilin LJ (1996) Phenolic content of various beverages determines the extent of inhibition of human serum and low-density lipoprotein oxidation in vitro: identification and mechanism of action of some cinnamic acid derivatives from red wine. Clin Sci 91:449–458

    Article  PubMed  CAS  Google Scholar 

  3. Filik H, Cetintas G, Avan AA, Aydar S, Koc SN, Boz I (2013) Square-wave stripping voltammetric determination of caffeic acid on electrochemically reduced graphene oxide-na-fion composite film. Talanta 116:245 – 25

  4. Vilian ATE, Chen SM, Chen YH, Ali MA, Al-Hemaid FMA (2014) An electrocatalytic oxidation and voltammetric method using a chemically reduced graphene oxide film for the determination of caffeic acid. J Colloid Interf Sci 423:33–40

    Article  CAS  Google Scholar 

  5. Sousa WR, da Rocha C, Cardoso CL, Silva DHS, Zanoni MVB (2004) Determination of the relative contribution of phenolic antioxidants in orange juice by voltammetric methods. J Food Compos Anal 17:619–633

    Article  CAS  Google Scholar 

  6. da Silva LF, Ramos Stradiotto N, Oliveira HP (2008) Determination of Caffeic Acid in Red Wine by Voltammetric Method. Electroanal 20:1252–1258

    Article  CAS  Google Scholar 

  7. Sordoń W, Salachna A, Jakubowska M (2016) Voltammetric determination of caffeic, syringic and vanillic acids taking into account uncertainties in both axes. J Electroanal Chem 764:23–30

    Article  CAS  Google Scholar 

  8. Karikalan N, Karthik R, Chen SM, Chen HA (2017) A voltammetric determination of caffeic acid in red wines based on the nitrogen doped carbon modified glassy carbon electrode. Sci Rep 7:45924

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  9. Peng YY, Liu FH, Ye JN (2005) Determination of phenolic acids and flavones in lonicera japonica thumb by capillary electrophoresis with electrochemical detection. Electroanal 17:356–362

    Article  CAS  Google Scholar 

  10. Franquet-Griell H, Checa A, Núñez O, Saurina J, Hernández-Cassou S, Puignou L (2012) Determination of polyphenols in spanish wines by capillary zone electrophoresis. Application to wine characterization by using chemometrics. J Agric Food Chem 60:8340–8349

    Article  PubMed  CAS  Google Scholar 

  11. Chu TY, Chang CH, Liao YC, Chen YC (2001) Microwave-accelerated derivatization processes for the determination of phenolic acids by gas chromatography–mass spectrometry. Talanta 54:1163–1171

    Article  PubMed  CAS  Google Scholar 

  12. Porgalı E, Büyüktuncel E (2012) Determination of phenolic composition and antioxidant capacity of native red wines by high performance liquid chromatography and spectrophototometric methods. Food Res Int 45:145–154

    Article  CAS  Google Scholar 

  13. Fracassetti D, Lawrence N, Tredoux AGJ, Tirelli A, Nieuwoudt HH, Du Toit WJ (2011) Quantification of catechin and caffeic acid in grape juice and wine by a novel ultra-performance liquid chromatography method. Food Chem 128:1136–1142

    Article  CAS  Google Scholar 

  14. Tian CL, Wang M, Liu XK, Wang HP, Zhao CJ (2014) HPLC quantification of nine chemical constituents from the five parts of Abutilon theophrasti Medic. J Chromatogr Sci 52:258–263

    Article  PubMed  CAS  Google Scholar 

  15. Diaconu M, Litescu C, Radu GL (2011) Bienzymatic sensor based on the use of redox enzymes and chitosan–MWCNT nanocomposite. Evaluation of total phenolic content in plant extracts. Microchim Acta 172:177–184

    Article  CAS  Google Scholar 

  16. Tian J, Liu SP, Liu ZF, Yang JD, Zhu JH, Qiao M, Hu XL (2014) Fluorescence quenching and spectrophotometric methods for the determination of daunorubicin with meso-tera (4-sulphophenyl) porphyrin as probe. Spectrochim Acta A 120:7–13

    Article  CAS  Google Scholar 

  17. Duan RL, Li CY, Liu SP, Liu ZF, Li YF, Zhu JH, Hu XL (2015) A selective fluorescence quenching method for the determination of trace hypochlorite in water samples with nile blue A. J Taiwan Inst Chem E 50:43–48

    Article  CAS  Google Scholar 

  18. Fan XQ, Liu SP, He YQ (2011) Study on the interaction of CdTe quantum dots with coumaric acid and caffeic acid based on fluorescence reversible tune. Colloid Surface B 88:23–30

    Article  CAS  Google Scholar 

  19. Xiang X, Shi JB, Huang FH, Zheng MM, Deng QC (2015) Quantum dots-based label-free fluorescence sensor for sensitive and non-enzymatic detection of caffeic acid. Talanta 141:182–187

    Article  PubMed  CAS  Google Scholar 

  20. Xu XY, Ray R, Gu YL, Ploehn HJ, Gearheart L, Raker K, Scrivens WA (2004) Electrophoretic analysis and purification of fluorescent single-walled carbon nanotube fragments. J Am Chem Soc 126:12736–12737

    Article  PubMed  CAS  Google Scholar 

  21. Zhu JH, Li MM, Liu SP, Liu ZF, Li YF, Hu XL (2015) Fluorescent carbon dots for auramine O determination and logic gate operation. Sens Actuators B Chem 219:261–267

    Article  CAS  Google Scholar 

  22. Yuan YS, Zhao X, Qiao M, Zhu JH, Liu SP, Yang JD, Hu XL (2016) Determination of sunset yellow in soft drinks based on fluorescence quenching of carbon dots. Spectrochim Acta A 167:106–110

    Article  CAS  Google Scholar 

  23. Devi P, Kaur G, Thakur A, Kaur N, Grewal A, Kumar P (2017) Waste derivitized blue luminescent carbon quantum dots for selenite sensing in water. Talanta 170:49–55

    Article  PubMed  CAS  Google Scholar 

  24. Wee SS, Ng YH, Ng SM (2013) Synthesis of fluorescent carbon dots via simple acid hydrolysis of bovine serum albumin and its potential as sensitive sensing probe for lead (II) ions. Talanta 116:71–76

    Article  PubMed  CAS  Google Scholar 

  25. Ma YH, Zhang Z, Xu YL, Ma M, Chen B, Wei L, Xiao LH (2016) A bright carbon-dot-based fluorescent probe for selective and sensitive detection of mercury ions. Talanta 161:476–481

    Article  PubMed  CAS  Google Scholar 

  26. Zhu JL, Sun S, Jiang K, Wang YH, Liu WQ, Lin HW (2017) A highly sensitive and selective fluorimetric probe for intracellular peroxynitrite based on photoinduced electron transfer from ferrocene to carbon dots. Biosens Bioelectron 97:150–156

    Article  PubMed  CAS  Google Scholar 

  27. Yang H, Yang L, Yuan YS, Pan S, Yang JD, Yan JJ, Zhang H, Sun QQ, Hu XL (2018) A portable synthesis of water-soluble carbon dots for highly sensitive and selective detection of chlorogenic acid based on inner filter effect. Spectrochim Acta A 189:139–146

    Article  CAS  Google Scholar 

  28. Zhang QY, Zhang CH, Li ZB, Ge JY, Li CZ, Dong C, Shuang SM (2015) Nitrogen-doped carbon dots as fluorescent probe for detection of curcumin based on the inner filter effect. Rsc Adv 5:95054–95060

    Article  CAS  Google Scholar 

  29. Yuan YS, Jiang JZ, Liu SP, Yang JD, zhang H, Yan JJ, Hu XL (2017) Fluorescent carbon dots for glyphosate determination based on fluorescence resonance energy transfer and logic gate operation. Sens Actuators B Chem 242:545–553

    Article  CAS  Google Scholar 

  30. Wang Q, Zhang SR, Zhong YG, Yang XF, Li Z, Li H (2017) Preparation of yellow-green-emissive carbon dots and their application in constructing a fluorescent turn-on nanoprobe for imaging of selenol in living cells. Anal Chem 89:1734–1741

    Article  PubMed  CAS  Google Scholar 

  31. Duan RL et al (2017) Spectrofluorometric determination of ascorbic acid using thiamine and potassium ferricyanide. Instrum Sci Technol 45:312–323

    Article  CAS  Google Scholar 

  32. Wang J, Liu HB, Park S, Kim SY, Joo T, Ha CS (2012) γ-Oxo-1-pyrenebutyric acid used for fluorescent detection of serum albumins and trypsin. Rsc Adv 2:4242–4249

    Article  CAS  Google Scholar 

  33. Evale BG, Hanagodimath SM (2010) Static and dynamic quenching of biologically active coumarin derivative by aniline in benzene-acetonitrile mixtures. J Lumin 130:1330–1337

    Article  CAS  Google Scholar 

  34. Li XL, Hu YJ, Wang H, Yu BQ, Yue HL (2012) Molecular spectroscopy evidence of berberine binding to DNA: comparative binding and thermodynamic profile of intercalation. Biomacromol 13:873–880

    Article  CAS  Google Scholar 

  35. Yuan YS, Yang L, Liu SP, Yang JD, Zhang H, Yan JJ, Hu XL (2017) Enzyme-catalyzed Michael addition for the synthesis of warfarin and its determination via fluorescence quenching of l-tryptophan. Spectrochim Acta A 176:183–188

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors gratefully acknowledge financial support for this study by grants of the National Natural Science Foundation of China (Grant no. 21705132; Grant no.21475014), the Special Fund of Chongqing Key Laboratory (CSTC) and the Fundamental Research Funds for the Central Universities (XDJK 2013A022).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Xiaoli Hu.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sun, Q., Long, Y., Li, H. et al. Fluorescent Carbon Dots as Cost-Effective and Facile Probes for Caffeic Acid Sensing via a Fluorescence Quenching Process. J Fluoresc 28, 523–531 (2018). https://doi.org/10.1007/s10895-018-2213-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-018-2213-8

Keywords

Navigation