Cyrene as solvent for metal nanoparticle synthesis
Source abstract
Abstract
Abstract Enormous advances have been made in the synthesis of metal nanoparticles (NPs) affording a high degree of control over their size, shape, and composition. In recent years, a growing effort has been dedicated to incorporating principles of green chemistry in different aspects of NPs, ranging from reagents/solvents to their fate in the environment. In this report, we focus on the use of Cyrene (dihydrolevoglucosenone) as an alternative green solvent for the synthesis of metal NPs. We begin with the synthesis of Ag NPs, given their prominence in the literature. Through control reactions, we show that Cyrene has a dual role of solvent and reducing agent. Additionally, the conversion yield for the Ag NPs synthesis was studied with respect to temperature and the Ag precursor. We then expand on the synthetic methodology to access Pd, Pt, and Bi NPs. The functionality of the synthesized NPs is assessed by employing them as electrocatalysts for furfural reduction and the hydrogen evolution reaction. We envision the use of Cyrene as a green solvent can be extended toward the synthesis of NPs of other metals and classes of materials. Graphical Abstract
Source: crossref · Quality: baseline
Research context
OpenAlex topics: Nanomaterials for catalytic reactions · Gold and Silver Nanoparticles Synthesis and Applications · Nanoparticles: synthesis and applications
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (58)
Show source-provided references
1. Klębowski B, Depciuch J, Parlińska-Wojtan M, Baran J (2018) Applications of noble metal-based nanoparticles in medicine. Int J Mol Sci 19:4031. https://doi.org/10.3390/ijms1912403110.3390/ijms19124031 ↗
2. Khursheed R, Dua K, Vishwas S, Gulati M, Jha NK, Aldhafeeri GM, Alanazi FG, Goh BH, Gupta G, Paudel KR, Hansbro PM, Chellappan DK, Singh SK (2022) Biomedical applications of metallic nanoparticles in cancer: current status and future perspectives. Biomed Pharmacother 150:112951. https://doi.org/10.1016/j.biopha.2022.11295110.1016/j.biopha.2022.112951 ↗
3. Liu L, Zhang X, Yang L, Ren L, Wang D, Ye J (2017) Metal nanoparticles induced photocatalysis. Natl Sci Rev 4:761–780. https://doi.org/10.1093/nsr/nwx01910.1093/nsr/nwx019 ↗
4. Park J, Kwon T, Kim J, Jin H, Kim HY, Kim B, Joo SH, Lee K (2018) Hollow nanoparticles as emerging electrocatalysts for renewable energy conversion reactions. Chem Soc Rev 47:8173–8202. https://doi.org/10.1039/C8CS00336J10.1039/C8CS00336J ↗
5. Jin R, Higaki T (2021) Open questions on the transition between nanoscale and bulk properties of metals. Commun Chem 4:28. https://doi.org/10.1038/s42004-021-00466-610.1038/s42004-021-00466-6 ↗
6. Baig N, Kammakakam I, Falath W (2021) Nanomaterials: a review of synthesis methods, properties, recent progress, and challenges. Mater Adv 2:1821–1871. https://doi.org/10.1039/D0MA00807A10.1039/D0MA00807A ↗
7. Ko Y-J, Lim C, Jin J, Kim MG, Lee JY, Seong T-Y, Lee K-Y, Min BK, Choi J-Y, Noh T, Hwang GW, Lee WH, Oh H-S (2024) Extrinsic hydrophobicity-controlled silver nanoparticles as efficient and stable catalysts for CO2 electrolysis. Nat Commun 15:3356. https://doi.org/10.1038/s41467-024-47490-310.1038/s41467-024-47490-3 ↗
8. Wrasman CJ, Zhou C, Aitbekova A, Goodman ED, Cargnello M (2022) Recycling of solvent allows for multiple rounds of reproducible nanoparticle synthesis. J Am Chem Soc 144:11646–11655. https://doi.org/10.1021/jacs.2c0283710.1021/jacs.2c02837 ↗
9. Fievet F, Lagier J, Blin B, Beaudoin B, Figlarz M (1989) Homogeneous and heterogeneous nucleations in the polyol process for the preparation of micron and submicron size metal particles. Solid State Ion 32–33:198–205. https://doi.org/10.1016/0167-2738(89)90222-110.1016/0167-2738(89)90222-1 ↗
10. Sun Y, Xia Y (2002) Large-scale synthesis of uniform silver nanowires through a soft, self-seeding, polyol process. Adv Mater 14:833–837. https://doi.org/10.1002/1521-4095(20020605)14:11%3c833::AID-ADMA833%3e3.0.CO;2-K10.1002/1521-4095(20020605)14:11<833::AID-ADMA833>3.0.CO;2-K ↗
11. Sun Y, Xia Y (2002) Shape-controlled synthesis of gold and silver nanoparticles. Science 298:2176–2179. https://doi.org/10.1126/science.107722910.1126/science.1077229 ↗
12. Kandasamy S, Samudrala SP, Bhattacharya S (2019) The route towards sustainable production of ethylene glycol from a renewable resource, biodiesel waste: a review. Catal Sci Technol 9:567–577. https://doi.org/10.1039/C8CY02035C10.1039/C8CY02035C ↗
13. Chen S, Penn RL (2019) Controlled growth of silver nanoparticle seeds using green solvents. Cryst Growth Des 19:4332–4339. https://doi.org/10.1021/acs.cgd.9b0005110.1021/acs.cgd.9b00051 ↗
14. Camp JE (2018) Bio-available solvent cyrene: synthesis, derivatization, and applications. Chemsuschem 11:3048–3055. https://doi.org/10.1002/cssc.20180142010.1002/cssc.201801420 ↗
15. Sherwood J, De bruyn M, Constantinou A, Moity L, McElroy CR, Farmer TJ, Duncan T, Raverty W, Hunt AJ, Clark JH (2014) Dihydrolevoglucosenone (Cyrene) as a bio-based alternative for dipolar aprotic solvents. Chem Commun 50:9650–9652. https://doi.org/10.1039/C4CC04133J10.1039/C4CC04133J ↗
16. Salavagione HJ, Sherwood J, De bruyn M, Budarin VL, Ellis GJ, Clark JH, Shuttleworth PS (2017) Identification of high performance solvents for the sustainable processing of graphene. Green Chem 19:2550–2560. https://doi.org/10.1039/C7GC00112F10.1039/C7GC00112F ↗
17. Zhang J, White GB, Ryan MD, Hunt AJ, Katz MJ (2016) Dihydrolevoglucosenone (Cyrene) as a green alternative to N, N-dimethylformamide (DMF) in MOF synthesis. ACS Sustain Chem Eng 4:7186–7192. https://doi.org/10.1021/acssuschemeng.6b0211510.1021/acssuschemeng.6b02115 ↗
18. Czapka A, Grune C, Schädel P, Bachmann V, Scheuer K, Dirauf M, Weber C, Skaltsounis A-L, Jandt KD, Schubert US, Fischer D, Werz O (2022) Drug delivery of 6-bromoindirubin-3’-glycerol-oxime ether employing poly(d, l-lactide-co-glycolide)-based nanoencapsulation techniques with sustainable solvents. J Nanobiotechnology 20:5. https://doi.org/10.1186/s12951-021-01179-710.1186/s12951-021-01179-7 ↗
19. Grune C, Thamm J, Werz O, Fischer D (2021) Cyrene™ as an alternative sustainable solvent for the preparation of poly(lactic-co-glycolic acid) nanoparticles. J Pharm Sci 110:959–964. https://doi.org/10.1016/j.xphs.2020.11.03110.1016/j.xphs.2020.11.031 ↗
20. Wiley BJ, Xiong Y, Li Z-Y, Yin Y, Xia Y (2006) Right bipyramids of silver: a new shape derived from single twinned seeds. Nano Lett 6:765–768. https://doi.org/10.1021/nl060069q10.1021/nl060069q ↗
21. Skrabalak SE, Au L, Li X, Xia Y (2007) Facile synthesis of Ag nanocubes and Au nanocages. Nat Protoc 2:2182–2190. https://doi.org/10.1038/nprot.2007.32610.1038/nprot.2007.326 ↗
22. Sun Y, Yin Y, Mayers BT, Herricks T, Xia Y (2002) Uniform silver nanowires synthesis by reducing AgNO3 with ethylene glycol in the presence of seeds and poly(vinyl pyrrolidone). Chem Mater 14:4736–4745. https://doi.org/10.1021/cm020587b10.1021/cm020587b ↗
23. Ashkarran AA, Bayat A (2013) Surface plasmon resonance of metal nanostructures as a complementary technique for microscopic size measurement. Int Nano Lett 3:50. https://doi.org/10.1186/2228-5326-3-5010.1186/2228-5326-3-50 ↗
24. Yamamoto M, Kashiwagi Y, Nakamoto M (2006) Size-controlled synthesis of monodispersed silver nanoparticles capped by long-chain alkyl carboxylates from silver carboxylate and tertiary amine. Langmuir 22:8581–8586. https://doi.org/10.1021/la060024510.1021/la0600245 ↗
25. Briggs D (1981) Handbook of X‐ray photoelectron spectroscopy C. D. Wanger, W. M. Riggs, L. E. Davis, J. F. Moulder and G. E.Muilenberg Perkin‐Elmer Corp., Physical Electronics Division, Eden Prairie, Minnesota, USA, 1979. 190 pp. $195. Surf Interface Anal 3:. https://doi.org/10.1002/sia.74003041210.1002/sia.740030412 ↗
26. De bruyn M, Budarin VL, Misefari A, Shimizu S, Fish H, Cockett M, Hunt AJ, Hofstetter H, Weckhuysen BM, Clark JH, Macquarrie DJ (2019) Geminal diol of dihydrolevoglucosenone as a switchable hydrotrope: a continuum of green nanostructured solvents. ACS Sustain Chem Eng 7:7878–7883. https://doi.org/10.1021/acssuschemeng.9b0047010.1021/acssuschemeng.9b00470 ↗
27. Skrabalak SE, Wiley BJ, Kim M, Formo EV, Xia Y (2008) On the polyol synthesis of silver nanostructures: glycolaldehyde as a reducing agent. Nano Lett 8:2077–2081. https://doi.org/10.1021/nl800910d10.1021/nl800910d ↗
28. Koczkur KM, Mourdikoudis S, Polavarapu L, Skrabalak SE (2015) Polyvinylpyrrolidone (PVP) in nanoparticle synthesis. Dalton Trans 44:17883–17905. https://doi.org/10.1039/C5DT02964C10.1039/C5DT02964C ↗
29. Washio I, Xiong Y, Yin Y, Xia Y (2006) Reduction by the end groups of poly(vinyl pyrrolidone): a new and versatile route to the kinetically controlled synthesis of Ag triangular nanoplates. Adv Mater 18:1745–1749. https://doi.org/10.1002/adma.20060067510.1002/adma.200600675 ↗
30. Narayanan R, El-Sayed MA (2003) Effect of catalysis on the stability of metallic nanoparticles: Suzuki reaction catalyzed by PVP-palladium nanoparticles. J Am Chem Soc 125:8340–8347. https://doi.org/10.1021/ja035044x10.1021/ja035044x ↗
31. Mazumder V, Sun S (2009) Oleylamine-mediated synthesis of Pd nanoparticles for catalytic formic acid oxidation. J Am Chem Soc 131:4588–4589. https://doi.org/10.1021/ja900491510.1021/ja9004915 ↗
32. Gao D, Zhou H, Wang J, Miao S, Yang F, Wang G, Wang J, Bao X (2015) Size-dependent electrocatalytic reduction of CO 2 over Pd nanoparticles. J Am Chem Soc 137:4288–4291. https://doi.org/10.1021/jacs.5b0004610.1021/jacs.5b00046 ↗
33. Erikson H, Sarapuu A, Tammeveski K, Solla-Gullón J, Feliu JM (2011) Enhanced electrocatalytic activity of cubic Pd nanoparticles towards the oxygen reduction reaction in acid media. Electrochem Commun 13:734–737. https://doi.org/10.1016/j.elecom.2011.04.02410.1016/j.elecom.2011.04.024 ↗
34. Coutanceau C, Urchaga P, Brimaud S, Baranton S (2012) Colloidal syntheses of shape- and size-controlled Pt nanoparticles for electrocatalysis. Electrocatalysis 3:75–87. https://doi.org/10.1007/s12678-012-0079-010.1007/s12678-012-0079-0 ↗
35. Arán-Ais RM, Yu Y, Hovden R, Solla-Gullón J, Herrero E, Feliu JM, Abruña HD (2015) Identical location transmission electron microscopy imaging of site-selective Pt nanocatalysts: electrochemical activation and surface disordering. J Am Chem Soc 137:14992–14998. https://doi.org/10.1021/jacs.5b0955310.1021/jacs.5b09553 ↗
36. Reetz MT, Westermann E (2000) Phosphane-free palladium-catalyzed coupling reactions: the decisive role of Pd nanoparticles. Angew Chem Int Ed 39:165–168. https://doi.org/10.1002/(SICI)1521-3773(20000103)39:1%3c165::AID-ANIE165%3e3.0.CO;2-B10.1002/(SICI)1521-3773(20000103)39:1<165::AID-ANIE165>3.0.CO;2-B ↗
37. Antonatos N, Elliott JD, Mazánek V, Marvan P, Carbone P, Geng W, Jing Y, Sofer Z (2022) Dealloying layered PdBi 2 nanoflakes to palladium hydride leads to enhanced electrocatalytic N2 reduction. J Mater Chem A 10:11904–11916. https://doi.org/10.1039/D1TA07395H10.1039/D1TA07395H ↗
38. Ghosh S, Manna L (2018) The many “facets” of halide ions in the chemistry of colloidal inorganic nanocrystals. Chem Rev 118:7804–7864. https://doi.org/10.1021/acs.chemrev.8b0015810.1021/acs.chemrev.8b00158 ↗
39. Zheng Y, Zeng J, Ruditskiy A, Liu M, Xia Y (2014) Oxidative etching and its role in manipulating the nucleation and growth of noble-metal nanocrystals. Chem Mater 26:22–33. https://doi.org/10.1021/cm402023g10.1021/cm402023g ↗
40. Lu N, Chen W, Fang G, Chen B, Yang K, Yang Y, Wang Z, Huang S, Li Y (2014) 5-fold twinned nanowires and single twinned right bipyramids of Pd: utilizing small organic molecules to tune the etching degree of O2/halides. Chem Mater 26:2453–2459. https://doi.org/10.1021/cm404220410.1021/cm4042204 ↗
41. Gomez C, Hallot G, Laurent S, Port M (2021) Medical applications of metallic bismuth nanoparticles. Pharmaceutics 13:1793. https://doi.org/10.3390/pharmaceutics1311179310.3390/pharmaceutics13111793 ↗
42. Zhang Z, Chi M, Veith GM, Zhang P, Lutterman DA, Rosenthal J, Overbury SH, Dai S, Zhu H (2016) Rational design of Bi nanoparticles for efficient electrochemical CO2 reduction: the elucidation of size and surface condition effects. ACS Catal 6:6255–6264. https://doi.org/10.1021/acscatal.6b0129710.1021/acscatal.6b01297 ↗
43. Zhou R, Liu X, Wu Y, Xiang H, Cao J, Li Y, Yin W, Zu Y, Li J, Liu R, Zhao F, Liu Z, Chen C, Gu Z, Yan L, Zhao Y (2020) Suppressing the radiation-induced corrosion of bismuth nanoparticles for enhanced synergistic cancer radiophototherapy. ACS Nano 14:13016–13029. https://doi.org/10.1021/acsnano.0c0437510.1021/acsnano.0c04375 ↗
44. Bi H, He F, Dong Y, Yang D, Dai Y, Xu L, Lv R, Gai S, Yang P, Lin J (2018) Bismuth nanoparticles with “light” property served as a multifunctional probe for X-ray computed tomography and fluorescence imaging. Chem Mater 30:3301–3307. https://doi.org/10.1021/acs.chemmater.8b0056510.1021/acs.chemmater.8b00565 ↗
45. Yang C, Guo C, Guo W, Zhao X, Liu S, Han X (2018) Multifunctional bismuth nanoparticles as theranostic agent for PA/CT imaging and NIR laser-driven photothermal therapy. ACS Appl Nano Mater 1:820–830. https://doi.org/10.1021/acsanm.7b0025510.1021/acsanm.7b00255 ↗
46. Mourdikoudis S, Antonatos N, Mazánek V, Marek I, Sofer Z (2022) Simple bottom-up synthesis of bismuthene nanostructures with a suitable morphology for competitive performance in the electrocatalytic nitrogen reduction reaction. Inorg Chem 61:5524–5538. https://doi.org/10.1021/acs.inorgchem.1c0393810.1021/acs.inorgchem.1c03938 ↗
47. Bera D, Kuiry SC, McCutchen M, Seal S, Heinrich H, Slane GC (2004) In situ synthesis of carbon nanotubes decorated with palladium nanoparticles using arc-discharge in solution method. J Appl Phys 96:5152–5157. https://doi.org/10.1063/1.178634710.1063/1.1786347 ↗
48. Wang J, Rathi S, Singh B, Lee I, Joh H-I, Kim G-H (2015) Alternating current dielectrophoresis optimization of Pt-decorated graphene oxide nanostructures for proficient hydrogen gas sensor. ACS Appl Mater Interfaces 7:13768–13775. https://doi.org/10.1021/acsami.5b0132910.1021/acsami.5b01329 ↗
49. Li X, Zhao H, Wang K, Sun Y, Xu M, Sheng X (2023) Ag nanoparticles/NiSx/ZnO nanorods/carbon fiber electrocatalysts for 5-hydroxymethyl furfural oxidation and p- nitrophenol reduction: implications for green chemical electrosynthesis applications. ACS Appl Nano Mater 6:9197–9205. https://doi.org/10.1021/acsanm.3c0068210.1021/acsanm.3c00682 ↗
50. Akhade SA, Singh N, Gutiérrez OY, Lopez-Ruiz J, Wang H, Holladay JD, Liu Y, Karkamkar A, Weber RS, Padmaperuma AB, Lee M-S, Whyatt GA, Elliott M, Holladay JE, Male JL, Lercher JA, Rousseau R, Glezakou V-A (2020) Electrocatalytic hydrogenation of biomass-derived organics: a review. Chem Rev 120:11370–11419. https://doi.org/10.1021/acs.chemrev.0c0015810.1021/acs.chemrev.0c00158 ↗
51. Bender MT, Yuan X, Goetz MK, Choi K-S (2022) Electrochemical hydrogenation, hydrogenolysis, and dehydrogenation for reductive and oxidative biomass upgrading using 5-hydroxymethylfurfural as a model system. ACS Catal 12:12349–12368. https://doi.org/10.1021/acscatal.2c0360610.1021/acscatal.2c03606 ↗
52. Shan N, Hanchett MK, Liu B (2017) Mechanistic insights evaluating Ag, Pb, and Ni as electrocatalysts for furfural reduction from first-principles methods. J Phys Chem C 121:25768–25777. https://doi.org/10.1021/acs.jpcc.7b0677810.1021/acs.jpcc.7b06778 ↗
53. Dong H, Chen Y-C, Feldmann C (2015) Polyol synthesis of nanoparticles: status and options regarding metals, oxides, chalcogenides, and non-metal elements. Green Chem 17:4107–4132. https://doi.org/10.1039/C5GC00943J10.1039/C5GC00943J ↗
54. Da Silva JL, Beluomini MA, Ramos Stradiotto N (2017) Cathodic electrochemical determination of furfural in sugarcane bagasse using an electrode modified with nickel nanoparticles. Anal Methods 9:826–834. https://doi.org/10.1039/C6AY03222B10.1039/C6AY03222B ↗
55. Long NV, Ohtaki M, Nogami M, Hien TD (2011) Effects of heat treatment and poly(vinylpyrrolidone) (PVP) polymer on electrocatalytic activity of polyhedral Pt nanoparticles towards their methanol oxidation. Colloid Polym Sci 289:1373–1386. https://doi.org/10.1007/s00396-011-2460-610.1007/s00396-011-2460-6 ↗
56. Li D, Wang C, Tripkovic D, Sun S, Markovic NM, Stamenkovic VR (2012) Surfactant removal for colloidal nanoparticles from solution synthesis: the effect on catalytic performance. ACS Catal 2:1358–1362. https://doi.org/10.1021/cs300219j10.1021/cs300219j ↗
57. Krishna SH, Huang K, Barnett KJ, He J, Maravelias CT, Dumesic JA, Huber GW, De Bruyn M, Weckhuysen BM (2018) Oxygenated commodity chemicals from chemo-catalytic conversion of biomass derived heterocycles. AIChE J 64:1910–1922. https://doi.org/10.1002/aic.1617210.1002/aic.16172 ↗
58. He J, Liu M, Huang K, Walker TW, Maravelias CT, Dumesic JA, Huber GW (2017) Production of levoglucosenone and 5-hydroxymethylfurfural from cellulose in polar aprotic solvent–water mixtures. Green Chem 19:3642–3653. https://doi.org/10.1039/C7GC01688C10.1039/C7GC01688C ↗