Abstract
A novel deep-ultraviolet and dual-emission carbon nanodots (DUCDs)-based dual-channel ratiometric probe was prepared by a one-pot environmental-friendly hydrothermal process using guanidine as the only starting material for sensing polyphenol in tea sample (TPPs). Under the exposure to TPPs, the DUCDs not only provided a characteristic colorimetric response to TPPs, but also displayed TPPs-sensitive ratiometric fluorescence quenching. The detection mechanism was proved to be that enrichment-specific hydroxyl sites (e.g., -NH2 and -COOH) of DUCDs can specifically react with phenolic hydroxyl groups of TPPs to generate dynamic amide and carboxylate bonds by dehydration and/or condensation reaction. As a result, a new carbon nanomaterial with decrement of surface passivation groups, inherent light-absorbing, and invalid fluorescence emission was generated. The ratio (FL297nm/FL395nm) of fluorescence intensity at 297 nm and 395 nm of DUCDs excited at 275 nm decreased with increasing TPPs concentration. The linearity range was 5.0 ng/mL to 100 µg/mL with a detection limit (DL) of 3.5 ± 0.04 ng/mL for TPPs (n = 3, 3σ/k). Colorimetry of DUCDs, best measured as absorbance at 320 nm, was increased linearly in the TPP concentration range 200 ng/mL–200 µg/mL with a DL of 94.7 ± 0.04 ng/mL (n = 3, 3σ/k). The probe was successfully applied to the determination of TPPs in real tea samples, showing potential application prospects in food analysis.
Graphical abstract
Similar content being viewed by others
References
He HF, Wei K, Yin J, Ye Y (2020) Insight into tea flavonoids: composition and chemistry. Food Rev Int 37:1–12
Saikrithika S, Senthil Kumar A (2020) Electrochemical detections of tea polyphenols: a review. Electroanalysis 32:2343–2360
Wei Q, Liu T, Pu H, Sun DW (2020) Development of a fluorescent microwave-assisted synthesized carbon dots/Cu2+ probe for rapid detection of tea polyphenols. J Food Process Eng 43:e13419
Fujiki H, Watanabe T, Sueoka E, Rawangkan A, Suganuma M (2018) Cancer prevention with green tea and its principal constituent, EGCG: from early investigations to current focus on human cancer stem cells. Mol Cell 41:73–82
Yan M, Shen X, Zhong S, Diao M, Zhao C, Xu Y, Zhang T (2021) Self-assembly system based on water-soluble perylene diimide for sensitive detection and discrimination of tea polyphenols. Dyes Pigments 186:108989
Kodagoda KHGK, Wickramasinghe I (2017) Health benefits of green and black tea: a review. Int J Adv Engi Res Sci 4:107–112
Okada F, Furuya K (1971) Inhibitory effect of tea catechins on some plant virus diseases. Chagyo Kenkyu Hokoku 1971:69–76
Yang Y, Zhang T (2019) Antimicrobial activities of tea polyphenol on phytopathogens: a review. Molecules 24:816
Chen Y, Cheng S, Dai J, Wang L, Xu Y, Peng X, Xie X, Peng C (2021) Molecular mechanisms and applications of tea polyphenols: a narrative review. J Food Biochem 45:e13910
Golden EB, Lam PY, Kardosh A, Gaffney KJ, Cadenas E, Louie SG, Petasis NA, Chen TC, Schönthal AH (2009) Green tea polyphenols block the anticancer effects of bortezomib and other boronic acid-based proteasome inhibitors. Blood 113:5927–5937
Nian B, Chen L, Yi C, Shi X, Jiang B, Jiao W, Liu Q, Lv C, Ma Y, Zhao M (2019) A high performance liquid chromatography method for simultaneous detection of 20 bioactive components in tea extracts. Electrophoresis 40:2837–2844
Roowi S, Stalmach A, Mullen W, Lean MEJ, Edwards CA, Crozier A (2010) Green tea flavan-3-ols: colonic degradation and urinary excretion of catabolites by humans. J Agric Food Chem 58:1296–1304
García-Villalba R, Espín JC, Tom’as-Barber’an FA, Rocha-Guzm’an NE (2017) Comprehensive characterization by LC-DAD-MS/MS of the phenolic composition of seven quercus leaf teas. J Food Compos Anal 63:38–46
Duan Y, Luo X, Qin Y, Zhang H, Sun G, Sun X, Yan Y (2013) Determination of epigallocatechin-3-gallate with a high-efficiency electrochemical sensor based on a molecularly imprinted poly(o-phenylenediamine) film. J Appl Polym Sci 129:2882–2890
Zhao S, Chen C, Li Z, Yuan Z, Lu C (2017) Hydroxyl radical induced chemiluminescence of hyperbranched polyethyleneimine protected silver nanoclusters and its application in tea polyphenols detection. Anal Methods 9:3114–3120
Xu X, Ye H, Wang W, Yu L, Chen G (2006) Determination of flavonoids in houttuynia cordata thunb. and saururus chinensis (Lour.) bail. by capillary electrophoresis with electrochemical detection. Talanta 68:759–764
Wang HF, Wu YY, Yan XP (2013) Room-temperature phosphorescent discrimination of catechol from resorcinol and hydroquinone based on sodium tripolyphosphate capped Mn-doped ZnS quantum dots. Anal Chem 85:1920–1925
Wang ZX, Yu XH, Li F, Kong FY, Lv WX, Wang W (2018) Multiplexed ratiometric photoluminescent detection of pyrophosphate using anisotropic boron-doped nitrogen-rich carbon rugby ball-like nanodots. J Mater Chem B 6:1771–1781
Huang T, Yan S, Yu Y, Xue Y, Yu Y, Han C (2022) Dual-responsive ratiometric fluorescent probe for hypochlorite and peroxynitrite detection and imaging in vitro and in vivo. Anal Chem 94:1415–1424
Cui F, Sun J, de Dieu HJ, Yang X, Ji J, Zhang Y, Lei H, Li Z, Zheng J, Fan M, Sun X (2019) Ultrasensitive fluorometric angling determination of staphylococcus aureus in vitro and fluorescence imaging in vivo using carbon dots with full-color emission. Anal Chem 91:14681–14690
Tong L, Wang X, Chen Z, Liang Y, Yang Y, Gao W, Liu Z, Tang B (2020) One-step fabrication of functional carbon dots with 90% fluorescence quantum yield for long-term lysosome imaging. Anal Chem 92:6430–6436
Wang ZX, Jin X, Wang WJ, Kong FY, Zhu J, Ding LHY, YJ, Wang W, (2021) Green synthesis of a deep-ultraviolet carbonized nanoprobe for ratiometric fluorescent detection of feroxacin and enrofloxacin in food and serum samples. Analyst 146:874–881
Wang ZX, Hu L, Gao YF, Kong FY, Li HY, Zhu J, Fang HL, Wang W (2020) Aggregation-induced emission behavior of dual-NIR-emissive zinc-doped carbon nanosheets for ratiometric anthrax biomarker detection. ACS Appl Bio Mater 3:9031–9042
Wang ZX, Gao YF, Yu XH, Kong FY, Lv WX, Wang W (2018) Photoluminescent coral-like carbon-branched polymers as nanoprobe for fluorometric determination of captopril. Microchim Acta 185:422
Bao L, Zhang ZL, Tian Q, Zhang L, Liu C, Lin Y, Qi B, Pang DW (2011) Electrochemical tuning of luminescent carbon nanodots: from preparation to luminescence mechanism. Adv Mater 23:5801–5806
Lin H, Gan T, Wu K (2009) Sensitive and rapid determination of catechol in tea samples using mesoporous Al-doped silica modified electrode. Food Chem 113:701–704
Zhou J, Zhou H, Tang J, Deng S, Yan F, Li W, Qu M (2017) Carbon dots doped with heteroatoms for fluorescent bioimaging: a review. Microchim Acta 184:343–368
Liu Q, Guo B, Rao Z, Zhang B, Gong JR (2013) Strong two-photon-induced fluorescence from photostable, biocompatible nitrogen-doped graphene quantum dots for cellular and deep-tissue imaging. Nano Lett 13:2436–2441
Zhu S, Zhang J, Tang S, Qiao C, Wang L, Wang H, Liu X, Li B, Li Y, Yu W, Wang X, Sun H, Yang B (2012) Surface chemistry routes to modulate the photoluminescence of graphene quantum dots: from fluorescence mechanism to up-conversion bioimaging applications. Adv Funct Mater 22:4732–4740
Shangguan J, He D, He X, Wang K, Xu F, Liu J, Tang J, Yang X, Huang J (2016) Label-free carbon-dots-based ratiometric fluorescence pH nanoprobes for intracellular pH sensing. Anal Chem 88:7837–7843
Bai J, Yuan G, Chen X, Zhang L, Zhu Y, Wang X, Ren L (2021) Simple strategy for scalable preparation carbon dots: RTP, time-dependent fluorescence, and NIR behaviors. Adv Sci 8:e2104278
Zhang Q, Wang R, Feng B, Zhong X, Ostrikov KK (2021) Photoluminescence mechanism of carbon dots: triggering high-color-purity red fluorescence emission through edge amino protonation. Nat Commun 12:6856
Yang H, Liu Y, Guo Z, Lei B, Zhuang J, Zhang X, Liu Z, Hu C (2019) Hydrophobic carbon dots with blue dispersed emission and red aggregation-induced emission. Nat Commun 10:1789
Song SY, Liu KK, Wei JY, Lou Q, Shang Y, Shan CX (2019) Deep-ultraviolet emissive carbon nanodots. Nano Lett 19:5553–5561
Liu KK, Song SY, Sui LZ, Wu SX, Jing PT, Wang RQ, Li QY, Wu GR, Zhang ZZ, Yuan KJ, Shan CX (2019) Efficient red/near-infrared-emissive carbon nanodots with multiphoton excited upconversion fluorescence. Adv Sci 6:1900766
Ding H, Yu SB, Wei JS, Xiong HM (2016) Full-color light-emitting carbon dots with a surface-state-controlled luminescence mechanism. ACS Nano 10:484–491
Lu S, Sui L, Liu J, Zhu S, Chen A, Jin M, Yang B (2017) Near-infrared photoluminescent polymer-carbon nanodots with two-photon fluorescence. Adv Mater 29:1603443
Zhu J, Hu J, Hu Q, Zhang X, Ushakova EV, Liu K, Wang S, Chen X, Shan C, Rogach AL, Bai X (2022) White light afterglow in carbon dots achieved via synergy between the room-temperature phosphorescence and the delayed fluorescence. Small 18:e2105415
Yu Y, Wang X, Jia X, Feng Z, Zhang L, Li H, He J, Shen G, Ding X (2021) Aptamer probes labeled with lanthanide-doped carbon nanodots permit dual-modal fluorescence and mass cytometric imaging. Adv Sci 8:e2102812
Zhou D, Li D, Jing P, Zhai Y, Shen D, Qu S, Rogach AL (2017) Conquering aggregation-induced solid-state luminescence quenching of carbon dots through a carbon dots-triggered silica gelation process. Chem Mater 29:1779–1787
Jiang K, Wang Y, Cai C, Lin H (2018) Conversion of carbon dots from fluorescence to ultralong room-temperature phosphorescence by heating for security applications. Adv Mater 30:1800783
Reckmeier CJ, Schneider J, Susha AS, Rogach AL (2016) Luminescent colloidal carbon dots: optical properties and effects of doping. Opt Express 24:A312–A340
Pan L, Sun S, Zhang A, Jiang K, Zhang L, Dong C, Huang Q, Wu A, Lin H (2015) Truly fluorescent excitation-dependent carbon dots and their applications in multicolor cellular imaging and multidimensional sensing. Adv Mater 27:7782–7787
Wang S, Liu P, Qin Y, Chen Z, Shen J (2016) Rapid synthesis of protein conjugated gold nanoclusters and their application in tea polyphenol sensing. Sensor Actuat B-Chem 223:178–185
Weyl DA, Murfin D (1966) Fluorescence of phto-degraded tyrosine solutions. Nature 212:921–922
Edelhoch H, Perlman RL, Wilchek M (1969) Tyrosine fluorescence of in proteins. Ann NY Acad Sci 158:391–409
Alghamdi A, Wellbrock T, Birch DJS, Vyshemirsky V, Rolinski OJ (2019) Cu2+ effects on beta-amyloid oligomerisation monitored by the fluorescence of intrinsic tyrosine. ChemPhysChem 20:3181–3185
Preston GW, Phillips DH (2016) Quantification of a peptide standard using the intrinsic fluorescence of tyrosine. Anal Bioanal Chem 408:2187–2193
Funding
Financial support for this work was provided by the National Natural Science Foundation of China (21705140, 21876144, 21974120), and the Natural Science Foundation of Jiangsu Province (BK20170474).
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of interest
The authors declare no competing interests.
Additional information
Publisher's note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Wang, ZX., Hu, L., Wang, WJ. et al. One-pot green preparation of deep-ultraviolet and dual-emission carbon nanodots for dual-channel ratiometric determination of polyphenol in tea sample. Microchim Acta 189, 241 (2022). https://doi.org/10.1007/s00604-022-05330-5
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s00604-022-05330-5