Abstract
4,4’-Dithiobisbenzoic acid (DTBA) is equivalent to two 4-mercaptobenzoic acid (pMBA) molecules connected together after losing H+, and this bimolecular mechanism of DTBA efficiently promotes the ionization reaction. Under the irradiation of laser light, DTBA molecules are broken to form bimolecules similar to pMBA, and this kind of bimolecular coupling greatly increases the probability of binding with Ag NPs. Also, this molecule has the carboxylic acid group, which leads to a certain sensitivity to pH. In this article, through the comparison of DTBA and pMBA parallel experiments, it is clear that DTBA has better Raman activity, higher reaction efficiency, and more stable reaction than pMBA. The occurrence of this highly efficient ionization reaction under the monitoring of surface-enhanced Raman spectroscopy (SERS) provides a certain value for the progress of further related reactions, and it also has a wide range of applications in pH sensors and intracellular pH monitoring.
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References
Ledesma C, Yang J, Chen D, Holmen A (2014) Recent approaches in mechanistic and kinetic studies of catalytic reactions using SSITKA technique. ACS Catal 4(12):4527–4547
Portz A, Baur M, Rinke G, Abb S, Rauschenbach S, Kern K, Durr M (2018) Chemical analysis of complex surface-adsorbed molecules and their reactions by means of cluster-induced desorption/ionization mass spectrometry. Anal Chem 90(5):3328–3334
Zhang Q, Blom DA, Wang H (2014) Nanoporosity-enhanced catalysis on subwavelength au nanoparticles: a Plasmon-enhanced spectroscopic study. Chem Mater 26(17):5131–5142
Agrawal A, Cho SH, Zandi O, Ghosh S, Johns RW, Milliron DJ (2018) Localized surface Plasmon resonance in semiconductor nanocrystals. Chem Rev 118(6):3121–3207
Gu XY, Liu JJ, Gao PF, Li YF, Huang CZ (2019) Gold triangular nanoplates based single-particle dark-field microscopy assay of pyrophosphate. Anal Chem 91:15798–15803
Paul KK, Giri PK, Sugimoto H, Fujii M, Choudhury B (2019) Evidence for plasmonic hot electron injection induced superior visible light photocatalysis by g-C3N4 nanosheets decorated with Ag–TiO2(B) and Au–TiO2(B) nanorods. Sol Energy Mater Sol Cells 201:110053
Fleischmann M, Hendra PJ, McQuillan AJ (1974) Raman spectra of pyridine adsorbed at a silver electrode. Chem Phys Lett 26(2):163–166
Albrecht MG, Creighton JA (1977) Anomalously intense Raman spectra of pyridine at a silver electrode. J Am Chem Soc 99(15):5215–5217
Huang Y, Fang Y, Yang Z, Sun M (2010) Can p,p '-dimercaptoazobisbenzene be produced from p-aminothiophenol by surface photochemistry reaction in the junctions of a Ag nanoparticle-molecule-Ag (or Au) film? J Phys Chem C 114(42):18263–18269
Samanta A, Maiti KK, Soh KS, Liao X, Chang Y-T (2011) Ultrasensitive near-infrared Raman reporters for SERS-based in vivo cancer detection. Angew Chem Int Ed Engl 50(27):6089–6092
Angelis FD, Gentile F, Mecarini F, Das G, Fabrizio ED (2011) Breaking the diffusion limit with super-hydrophobic delivery of molecules to plasmonic nanofocusing SERS structures. Nat Photonics 5(11):682–687
Polavarapu L, Porta AL, Novikov SM, Coronadopuchau M, Lizmarzán LM (2014) SERS: pen-on-paper approach toward the design of universal surface enhanced Raman scattering substrates (Small 15/2014). 10(15):3065–3071
Rycenga M, Wang Z, Gordon E, Cobley CM, Schwartz AG, Lo CS, Xia Y (2010) Probing the photothermal effect of gold-based nanocages with surface-enhanced Raman scattering (SERS). Angew Chem Int Ed Engl 48(52):9924–9927
Wang F, Widejko RG, Yang Z, Nguyen KT, Chen H, Fernando LP, Christensen KA, Anker JN (2012) Surface-enhanced raman scattering detection of pH with silica-encapsulated 4-mercaptobenzoic acid-functionalized silver nanoparticles. Anal Chem 84(18):8013–8019
Michota A, Bukowska J (2003) Surface-enhanced Raman scattering (SERS) of 4-mercaptobenzoic acid on silver and gold substrates. J Raman Spectrosc 34(1):21–25
Turkowicz M, Jastrzebska I, Hryniewicka M, Kotowska U, Gudalewska D, Karpinska J (2019) Investigation of lipoic acid - 4-methoxybenzyl alcohol reaction and evaluation of its analytical usefulness. Food Chem 125750
Zhang X, Yu Z, Ji W, Sui H, Cong Q, Wang X, Zhao B (2015) Charge-transfer effect on surface-enhanced Raman scattering (SERS) in an ordered Ag NPs/4-mercaptobenzoic acid/TiO2 system. J Phys Chem C 119(39):22439–22444
Shen C, Zhang P, Sun Q, Bai S, Hor TSA, Liu X (2015) Recent advances in C-S bond formation via C-H bond functionalization and decarboxylation. Chem Soc Rev 44(1):291–314
Kong DL, Cheng L, Wu H, Li Y, Liu L (2015) Metal-free yne-addition/1,4-aryl migration/decarboxylation cascade reaction of alkynoates with Csp3-H centers. Org Biomol Chem 14(7):2210–2217
Maltzahn GV, Centrone A, Park JH, Ramanathan R, Bhatia SN (2009) SERS-coded gold nanorods as a multifunctional platform for densely multiplexed near-infrared imaging and photothermal heating. Adv Mater 21(31):3175–3180
Mehrvar L, Sadeghipari M, Tavassoli SH, Mohajerzadeh S (2017) Surface-enhanced Raman spectroscopy of dye molecules on Ag-modified silicon nanowire substrates: influence of photoinduced probe degradation on enhancement factors. J Raman Spectrosc 48(9):1171–1181
Gu Z, Tian S, Zhou Q, Wei W, Zhao L, Li X, Zheng J (2013) Surface enhanced Raman scattering of molecules related to highly ordered gold cavities. J Raman Spectrosc 44(12):1682–1688
Kleppisius A, Kick A, Mertig M (2017) Double-layer capacitance of pH-sensitive self-assembled thiol layers on gold determined by electrical impedance spectroscopy in a microfluidic channel. Phys Status Solidi (a) 214(9):1600921
Funding
This work was supported by the LiaoNing Revitalization Talents Program (Grant No. XLYC1807162), the Shenyang High-Level Innovative Talents Program (Grant No. RC180227), the National Natural Science Foundation of China (Grant No. 21671089 and 11974152), the Scientific Research Fund of Liaoning Province (Grant No. 2019-ZD-0487), the Liaoning Provincial Department of Education Project (Grant No. LJC201904).
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Yang, Y., Zhang, H., Ma, L. et al. The Efficient Ionization Reaction of DTBA Achieved by Surface Plasmon Catalysis Effect. Plasmonics 15, 1525–1532 (2020). https://doi.org/10.1007/s11468-020-01175-x
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DOI: https://doi.org/10.1007/s11468-020-01175-x