Abstract
In this study, a photoelectrochemical (PEC) sensor based on perylene diimide derivatives (PDIs) was developed for the ultrasensitive quantification of dopamine (DA). PDIs were able to form self-assembled semiconductor nanostructures by strong π-π stacking, suitable for photoactive substances. Moreover, the shape of the PDI significantly affected the PEC properties of these nanostructures. The results showed that amino PDI with two-dimensional (2D) wrinkled layered nanostructures exhibited superior PEC properties relative to one-dimensional (1D) nanorods and fiber-based nanostructures (methyl and carboxyl PDIs). Based on these results, a mechanism for PEC sensor action was then proposed. The presence of 2D amino-PDI resulted in accelerated charge separation and transport. Furthermore, dopamine acted as effective electron donor to cause an increase in photocurrent. The as-obtained sensor was then used to detect small molecules like DA. A blue light optimized sensor at an applied potential of 0.7 V showed a detection limit of 1.67 nM with a wide linear range of 5 nM to 10 μM. On the other hand, the sensor presented acceptable reliability in determining DA in real samples. A recovery rate between 97.99 and 101.0% was obtained. Overall, controlling the morphology of semiconductors can influence PEC performance, which is a useful finding for the future development of PEC sensors.
Graphical Abstract
Similar content being viewed by others
References
Zhao W, Xu J, Chen H. Photoelectrochemical DNA biosensors. Chem Rev. 2014;114:7421–41.
Zhao W, Xu J, Chen H. Photoelectrochemical bioanalysis: the state of the art. Chem Soc Rev. 2015;44:729–41.
Li Y, Zhang N, Zhao W, Jiang D, Xu J, Chen H. Polymer dots for photoelectrochemical bioanalysis. Anal Chem. 2017;89:4945–50.
Chen Y, Yin H, Li F, Zhou J, Wang L, Wang J, Ai S. Polydopamine-sensitized WS2/black-TiO2 heterojunction for histone acetyltransferase detection with enhanced visible-light-driven photoelectrochemical activity. Chem Eng J. 2020;393: 124707.
Fu Y, Ding F, Chen J, Liu M, Zhang X, Du C, Si S. Label-free and near-zero-background-noise photoelectrochemical assay of methyltransferase activity based on a Bi2S3/Ti3C2 schottky junction. Chem Commun. 2020;56:5799–802.
Wei W, Liu D, Wei Z, Zhu Y. Short-range π–π stacking assembly on P25 TiO2 nanoparticles for enhanced visible-light photocatalysis. ACS Catal. 2016;7:652–63.
Luo YN, Tan XC, Young DJ, Chen QY, Huang YH, Feng DF, Ai CH, Mi Y. A photoelectrochemical aptasensor for the sensitive detection of streptomycin based on a TiO2/BiOI/BiOBr heterostructure. Anal Chim Acta. 2020;1115:33–40.
Tan C, Cao X, Wu X, He Q, Yang J, Zhang X, Chen J, Zhao W, Han S, Nam G, Sindoro M, Zhang H. Recent advances in ultrathin two-dimensional nanomaterials. Chem Rev. 2017;117:6225–331.
Hartnett P, Timalsina A, Matte H, Zhou N, Guo X, Zhao W, Facchetti A, Chang R, Hersam M, Wasielewski M, Marks T. Slip-stacked perylenediimides as an alternative strategy for high efficiency nonfullerene acceptors in organic photovoltaics. J Am Chem Soc. 2014;136:16345–56.
Zhang Y, Zheng Y, Li M, Hu T, Yuan R, Wei S. Cosensitization strategy with cascade energy level arrangement for ultrasensitive photoelectrochemical protein detection. Anal Chem. 2018;90:12278–83.
Perk B, Büyüksünetçi YT, Çetin R, Hakli Ö, Anik Ü. Electrochemical sensor based on perylene diimide derivative modified electrode. Monatsh Chem. 2021;152:193–9.
Zhang J, Li Y, Huang J, Hu H, Zhang G, Ma T, Chow P, Ade H, Pan D, Yan H. Ring-fusion of perylene diimide acceptor enabling efficient nonfullerene organic solar cells with a small voltage loss. J Am Chem Soc. 2017;139:16092–5.
Singh P, Mittal L, Kumar K, Sharma P, Bhargava G, Kumar S. Multifunctional metallo-supramolecular interlocked hexagonal microstructures for the detection of lead and thiols in water. Chem Commun. 2018;54:9482–5.
Hu R, Zhang X, Xu Q, Lu D, Yan Y, Xu Q, Ruan Q, Mo L, Zhang X. Universal aptameric biosensor: multiplexed detection of small analytes via aggregated perylene-based broad-spectrum quencher. Biosens Bioelectron. 2017;92:40–6.
Roy R, Sajeev NR, Sharma V, Koner AL. Aggregation induced emission switching based ultrasensitive ratiometric detection of biogenic diamines uing a perylenediimide-based smart fluoroprobe. ACS Appl Mater Interfaces. 2019;11:47207–17.
Krieg E, Weissman H, Shirman E, Shimoni E, Rybtchinski B. A recyclable supramolecular membrane for size-selective separation of nanoparticles. Nat Nanotechnol. 2011;6:141–6.
Datar A, Balakrishnan K, Zang L. One-dimensional self-assembly of a water soluble perylene diimide molecule by pH triggered hydrogelation. Chem Commun. 2013;49:6894–6.
Zhang J, Tan L, Jiang W, Hu W, Wang Z. N-alkyl substituted di(perylene bisimides) as air-stable electron transport materials for solution-processible thin-film transistors with enhanced performance. J Mater Chem C. 2013;1:3200–6.
Zhang S, Wang X, Huang Y, Zhai H, Liu Z. Ammonia sensing properties of perylene diimides: effects of core-substituted chiral groups. Sens Actuators B Chem. 2018;254:805–10.
Vajiravelu S, Ramunas L, Vidas GJ, Valentas G, Vygintas J, Valiyaveettil S. Effect of substituents on the electron transport properties of bay substituted perylene diimide derivatives. J Mater Chem. 2009;19:4268–75.
Yang C, Hu K, Wang D, Zubi Y, Lee S, Puthongkham P, Mirkin M, Venton B. Cavity carbon-nanopipette electrodes for dopamine detection. Anal Chem. 2019;91:4618–24.
Tang Y, Lv X, Gou W, Zhou X, Hao J, Feng J, Qi Y, Hu L, Yan Z. Ag nanozyme strengthened by folic acid: superior peroxidase-mimicking activity and application for visual monitoring of dopamine. Anal Bioanal Chem. 2022;414:6611–20.
Chang C, Lee C, Tai N. Nitrogen-incorporated ovoid-shaped nanodiamond films for dopamine detection. ACS Appl Nano Mater. 2020;3:11970–8.
Jiang L, Liu S, Ren L, Zhang P, Zhao X, Wang Y. Gold nanoparticles and invertase-based aptasensor for detection of dopamine hydrochloride. Food Sci. 2018;39:301–5.
Younus AR, Iqbal J, Muhammad N, Rehman F, Tariq M, Niaz A, Badshah S, Saleh TA, Rahim A. Nonenzymatic amperometric dopamine sensor based on a carbon ceramic electrode of type SiO2/C modified with Co3O4 nanoparticles. Microchim Acta. 2019;186:471.
Sun C, Shen J, Cui R, Yuan F, Zhang H, Wu X. Silver nanoflowers-enhanced Tb(III)/La(III) co-luminescence for the sensitive detection of dopamine. Anal Bioanal Chem. 2019;411:1375–81.
Kruss S, Salem DP, Vukovic L, Lima B, Vander Ende E, Boyden ES, Strano MS. High-resolution imaging of cellular dopamine efflux using a fluorescent nanosensor array. Proc Natl Acad Sci U S A. 2017;114(8):1789–94.
Du J, Yue R, Ren F, Yao Z, Jiang F, Yang P, Du Y. Novel graphene flowers modified carbon fibers for simultaneous determination of ascorbic acid, dopamine and uric acid. Biosens Bioelectron. 2014;53:220–4.
Ören T, Birel Ö, Anık Ü. Electrochemical determination of dopamine using a novel perylenediimide-derivative modified carbon paste electrode. Anal Lett. 2018;51:1680–93.
Varol TÖ, Perk B, Avci O, Akpolat O, Hakli Ö, Xue C, Anik Ü. Fabrication of graphene/azobenzene-perylene diimide derivative modified electrochemical sensors for the dopamine detection based on full factorial experimental design. Measurement. 2019;147: 106867.
Somayeh T, Hadi B. A Sensitive chlorpromazine voltammetric sensor based on graphene oxide modified glassy carbon electrode. Anal Bioanal Chem Res. 2019;6:171–82.
Hassan KM, Hadi B, Senthil K, Somayeh T, Peyman MJ, Fatemeh K, Ceren K, Yasser V, Mehdi B, Jalal R, Pau LS, Saravanan R, Li F, Najmeh Z. Recent advances in carbon nanomaterials-based electrochemical sensors for food azo dyes detection. Food Chem Toxicol. 2022;164: 112961.
Hadi B, Mohammad MA, Hossein N, Bahram G. Electrochemical characterization of 2, 2’-[1, 2-ethanediylbis (nitriloethylidyne)]-bis-hydroquinone-carbon nanotube paste electrode and its application to simultaneous voltammetric determination of ascorbic acid and uric acid. J Solid State Electr. 2009;13:353–63.
Zhang P, Zhu Q, Soomro RA, He S, Sun N, Qiao N, Xu B. In situ ice template approach to fabricate 3D flexible MXene film-based electrode for high performance supercapacitors. Adv Funct Mater. 2020;30:2000922.
Machín A, Fontánez K, Arango JC, Ortiz D, León JD, Pinilla S, Nicolosi V, Petrescu FI, Morant C, Márquez F. One-dimensional (1D) nanostructured materials for energy applications. Materials. 2021;14:2609.
Naqvi S, Kumar M, Kumar R. Facile synthesis and evaluation of electron transport and photophysical properties of photoluminescent PDI derivatives. ACS Omega. 2019;4:19735–45.
Bian Y, Chen J, Xu S, Zhou Y, Zhu L, Xiang Y, Xia D. The effect of a hydrogen bond on the supramolecular self-aggregation mode and the extent of metal-free benzoxazole-substituted phthalocyanines. New J Chem. 2015;39:5750–8.
Babaei H, McGaughey A, Wilmer C. Effect of pore size and shape on the thermal conductivity of metal-organic frameworks. Chem Sci. 2017;8:583–9.
Zhang X, Chi K, Li D, Deng Y, Ma Y, Xu Q, Hu R, Yang Y. 2D-porphrinic covalent organic framework-based aptasensor with enhanced photoelectrochemical response for the detection of C-reactive protein. Biosens Bioelectron. 2019;129:64–71.
Wen J, Xie J, Zhang H, Zhang A, Liu Y, Chen X, Li X. Constructing multi-functional metallic Ni interfacelayers in the g-C3N4 nanosheets/amorphous NiS heterojunctions for efficient photocatalytic H2 generation. ACS Appl Mater Interfaces. 2017;9:14031–42.
Teng Y, Jia X, Li J, Wang E. Ratiometric Fluorescence detection of tyrosinase activity and dopamine using thiolate-protected gold nanoclusters. Anal Chem. 2015;87:4897–902.
Maheshwaran S, Tamilalagan E, Chen S, Akilarasan M, Huang Y, AlMasoud N, Abualnaja KM, Ouladsmne M. Rationally designed f-MWCNT-coated bismuth molybdate (f-MWCNT@BMO) nanocomposites for the voltammetric detection of biomolecule dopamine in biological samples. Microchim Acta. 2021;188:315.
Zhang Y, Ren W, Fan Y, Dong J, Zhang H, Luo H, Li N. Label-free fluorescent discrimination and detection of epinephrine and dopamine based on bioinspired in situ copolymers and excitation wavelength switch. Anal Chim Acta. 2019;1054:167–75.
Yang J, Hu Y, Li Y. Molecularly imprinted polymer-decorated signal on-off ratiometric electrochemical sensor for selective and robust dopamine detection. Biosens Bioelectron. 2019;135:224–30.
Zhang Y, Xu M, Gao P, Gao W, Bian Z, Jia N. Photoelectrochemical sensing of dopamine using gold-TiO2 nanocomposites and visible-light illumination. Microchim Acta. 2019;186:326.
Wang H, Ye H, Zhang B, Zhao F, Zeng B. Synthesis of ZnIn2S4/CdS heterostructure based on electrostatic interaction mechanism for the indirect photoelectrochemical detection of dopamine. J Phys Chem C. 2018;122:20329–36.
Velmurugan S, Yang C-K. Fabrication of high-performance molybdenum disulfide graphitic carbon nitride p-n heterojunction stabilized rGO/ITO photoelectrode for photoelectrochemical determination of dopamine. ACS Appl Electron Mater. 2020;9:2845–56.
Chen Y, Li X, Cai G, Li M, Tang D. In situ formation of (0 0 1)TiO2/Ti3C2 heterojunctions for enhanced photoelectrochemical detection of dopamine. Electrochem Commun. 2021;125: 106987.
Acknowledgements
This work is supported by grants awarded by the National Natural Science Foundation of China (Grants 21864026 and 21605130) and the Natural Science Foundation of Yunnan Province (Grants 2018FB016 and 2016FD017).
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of Interest
The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
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
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Chi, KN., Liu, JW., Guan, Y. et al. Effect of perylene assembly shapes on photoelectrochemical properties and ultrasensitive biosensing behaviors toward dopamine. Anal Bioanal Chem 415, 5845–5854 (2023). https://doi.org/10.1007/s00216-023-04865-7
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00216-023-04865-7