Abstract
Water splitting reaction is a bottleneck for the environmentally safe production of hydrogen (H2) and oxygen (O2). Catalysts with high effectualness, extended durability, and affordable are the most important factors for water splitting. Porphyrin-based materials are promising electro-catalysts for the oxygen evolution reaction. In this project, we synthesized porphyrin-based N4-macrocyclic complex Tetraether bridged benzylideneamino mercaptopropanoic acid substituted Cobalt phthalocyanine (TEBMPCoPc) and characterized by different spectro-analytical techniques like FT-IR, NMR, Mass, XRD, TGA, and FESEM. The hybrid composite was produced by ball-milling TEBMPCoPc with reduced graphene oxide (rGO). The prepared hybrid catalyst TEBMPCoPc + rGO is used for the water oxidation reaction in 1 M KOH. Surprisingly, TEBMPCoPc + rGO exhibits a better catalytic activity towards hydrogen production through Oxygen evolution reaction (OER) with a subsidiary overpotential of 364 mV required to reach the current density of 10 mA cm−2, with a lower Tafel slope value of 56 mV/dec for an OER. Besides, TEBMPCoPc + rGO portrays decent time durability of 12 h and stability.
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Abbaspour A, Mirahmadi E (2013) Electrocatalytic activity of iron and nickel phthalocyanines supported on multi-walled carbon nanotubes towards oxygen evolution reaction. Electrochim Acta 105:92–98. https://doi.org/10.1016/j.electacta.2013.04.143
Alvarez IB, Wu Y, Sanchez J, Ge Y, Ramos-Garcés MV, Chu T, Jaramillo TF, Colón JL, Villagrán D (2021) Cobalt porphyrin intercalation into zirconium phosphate layers for electrochemical water oxidation. Sustain Energy Fules 5:430–437. https://doi.org/10.1039/D0SE01134G
Aralekallu S, Sajjan VA, Palanna M, Prabhu KCP, Hojamberdiev MB, Sannegowda LK (2020) Ni foam-supported azo linkage cobalt phthalocyanine as an efficient electrocatalyst for oxygen evolution reaction. J Power Sources 449:227516. https://doi.org/10.1016/j.jpowsour.2019.227516
Bhunia S, Bhnia K, Patra BC, Das SK, Pradhan D, Bhaumik A, Pradhan A, Bhattacharya S (2018) Efficacious electrochemical oxygen evolution from a novel Co(II) porphyrin/pyrene-based conjugated microporous polymer. ACS Appl Mater Interfaces 11:1520–1528. https://doi.org/10.1021/acsami.8b20142
Chandrakala KB, Giddaerappa RKRV, Shivaprasad KH (2022) Investigational undertaking descriptors for reduced graphene oxide-phthalocyanine composite based catalyst for electrochemical oxygen evolution reaction. J Electroanal Chem 3919:116558. https://doi.org/10.1016/j.jelechem.2022.116558
Dey RS, Hajra S, Sahu RK, Raj CR, Panigrahi MK (2012) A rapid room temperature chemical route for the synthesis of graphene: metal-mediated reduction of graphene oxide. Chem Commun 48:787–1789. https://doi.org/10.1039/C2CC16031E
Giddaerappa MN, Shantharaja HM, Sannegowda LK (2022a) Tetraphenolphthalein cobalt (II) phthalocyanine polymer modified with multiwalled carbon nanotubes as an efficient catalyst for the oxygen reduction reaction. ACS Omega 16:14291–14304. https://doi.org/10.1021/acsomega.2c01157
Giddaerappa MN, Mohammed I, Sannegowda LK (2022b) Mannich reaction derived phthalocyanine polymer for electrochemical detec- tion of salicylic acid. Inorg Chim Acta 512:119895. https://doi.org/10.1016/j.ica.2020.119895
Gonclaves JM, Silva MID, Angnes L, Araki K (2020) Vanadium-containing electro and photocatalysts for the oxygen evolution reaction: a review. J Mater Chem A 8:2171–2206. https://doi.org/10.1039/C9TA10857B
Iandolo B, Wickman B, Zoric I, Hellman A (2015) The raise of hematite: origin and strategies to reduce the high onset potential for the oxygen evolution reaction. J Mater Chem A 3:16896–169124. https://doi.org/10.1039/C5TA03362D
Karaoglu HRP, Gul A, Kocak MB (2008) Synthesis and characterization of a new tetracationic phthalocyanine. Dyes Pigm 76:231–235. https://doi.org/10.1016/j.dyepig.2006.08.032
Kong X, Zhu T, Cheng F, Zhu M, Cao X, Liang S, Cao G, Pan A (2018) Uniform MnCo2O4 porous dumbbells for lithium-ion batteries and oxygen evolution reactions. ACS Appl Mater Interfaces 10:8730–8738. https://doi.org/10.1021/acsami.7b19719
Kreider ME, Gallo A, Back S, Liu Y, Siahrostami S, Nordlund D, Sinclair R, Norskov JK, King LA, Jaramillo TF (2019) Precious metal-free nickel nitride catalyst for the oxygen reduction reaction. Appl Mater Interfaces 30:26863–26871. https://doi.org/10.1021/acsami.9b07116
Lee J, Lee H, Lim B (2018) Chemical transformation of iron alkoxide nanosheets to FeOOH nanoparticles for highly active and stable oxygen evolution electrocatalysts. J Ind Eng Chem 58:100–104. https://doi.org/10.1016/j.jiec.2017.09.013
Lei H, Zhang Q, Liang Z, Guo H, Wang Y, Lv H, Li X, Zhang W, Apfel U, Cao R (2022) Metal-corrole-based porous organic polymers for electrocatalytic oxygen reduction and evolution reactions. Angew Chem Int 134:e202201104. https://doi.org/10.1002/ange.202201104
Lever ABP (1999) The phthalocyanines—molecules of enduring value; a two-dimensional analysis of redox potentials. J Porphyr Phthalocyan 3:488–499. https://doi.org/10.1002/(SICI)1099-1409(199908/10)3:6/7%3C488::AID-JPP167%3E3.0.CO;2-K
Li M, Bo X, Zhang Y, Han C, Guo L (2014) Comparative study on the oxygen reduction reaction electrocatalytic activities of iron phthalocyanines supported on reduced graphene oxide, mesoporous carbon vesicle, and ordered mesoporous carbon. J Power Sources 264:114–122. https://doi.org/10.1016/j.jpowsour.2014.04.101
Li H, He Y, Yang Q, Wang J, Yan S, Chen C, Chen J (2019) Urchin-like Ni@N-doped carbon composites with Ni nanoparticles encapsulated in Ndoped carbon nantubes as high-efficient electrocatalyst for oxygen evolution reaction. J Solid State Chem 278:120843. https://doi.org/10.1016/j.jssc.2019.07.004
Li M, Hu Q, Shan H, Yu W, Xu Z (2021) Fabrication of copper phthalocyanine/reduced graphene oxide nanocomposites for efficient photocatalytic reduction of hexavalent chromium. Chemosphere 263:128250. https://doi.org/10.1016/j.chemosphere.2020.128250
Li J, Tang Y, Wang H, Wang C, Tian J, Liu D, Ming LC, Guo C (2022) Oxygen plasma induced interfacial CoOx/phthalocyanine cobalt as bifunctional electrocatalyst towards oxygen-involving reactions. Int J Hydrog Energy 47:9905–9914. https://doi.org/10.1016/j.ijhydene.2022.01.067
Liu J, Wang Z, Su K, Xv D, Zhao D, Li J, Tong H, Qian D, Yang C, Lu Z (2019) Self-supported hierarchical IrO2@NiO nanoflake arrays as an efficient and durable catalyst for electrochemical oxygen evolution. ACS Appl Mater Interfaces 29:25854–25862. https://doi.org/10.1021/acsami.9b05785
Madhuri KP, John NS (2018) Supercapacitor application of nickel phthalocyanine nanofibres and its composite with reduced graphene oxide. Appl Surf Sci 449:528–536
Magadla A, Oluwole DO, Managa M, Nyokong T (2019) Physicochemical and antimicrobial photodynamic chemotherapy (against E. coli) by indium phthalocyanines in the presence of silver–iron bimetallic nanoparticles. Polyhedron 162:30–38. https://doi.org/10.1016/j.poly.2019.01.032
Marcano DC, Kosynkin DV, Berlin JM, Sinitskii A, Sun Z, Slesarev A, Alemany LB, Lu W, Tour JM (2010) Improved synthesis of graphene oxide. ACS Nano 4:4806–4814. https://doi.org/10.1021/nn1006368
Marinescu C, Ali MB, Abderrahmane Hamdi A, Cherifi Y, Barras A, Coffinier Y, Somacescr S, Raditoiu V, Szunerits S, Boukherroub R (2018) Cobalt phthalocyanine-supported reduced graphene oxide: a highly efficient catalyst for heterogeneous activation of peroxymonosulfate for rhodamine B and pentachlorophenol degradation. Chem Eng J 336:465–475. https://doi.org/10.1016/j.cej.2017.12.009
Mounesh RKRV (2020) The electrochemical investigation of carboxamide-PEG2-biotin-CoPc using composite MWCNTs on modified GCE: the sensitive detections for glucose and hydrogen peroxide. New J Chem 44:3330–3340. https://doi.org/10.1039/C9NJ05807A
Nemkal M, Giddaerappa S, Sajjan VA, Sannegowda LK (2021) Novel amide coupled phthalocyanines: Synthesis and structure-property relationship for electrocatalysis and sensing of hydroquinone. J Electroanal Chem 898:115657. https://doi.org/10.1016/j.jelechem.2021.115657
Nouri E, Mohammadi RM, Xu Z, Dracopoulos V, Lianos P (2018) Improvement of the photovoltaic parameters of perovskite solar cells using a reduced-graphene-oxide-modified titania layer and soluble copper phthalocyanine as a hole transporter. Phys Chem Chem Phys 20:2388–2395. https://doi.org/10.1039/C7CP04538G
Nozari-Asbemarz M, Amiri M, Khodayari A, Bezaatpour A, Nouhi S, Hosseini P, Wark M, Boukherroub R, Szuneits S (2021) In situ synthesis of Co3O4/CoFe2O4 derived from a metal−organic framework on nickel foam: high-performance electrocatalyst for water oxidation. ACS Appl Energy 4:2951–2959. https://doi.org/10.1021/acsaem.1c00429
Pawar RC, Cho D, Lee CS (2013) Fabrication of nanocomposite photocatalysts from zinc oxide nanostructures and reduced graphene oxide. Curr Appl Phys. https://doi.org/10.1016/j.cap.2012.12.031
Prabhu CPK, Manjunath N, Shambulinga A, Imadadulla M, Shivaprasad KH, Amshumali MK, Lokesh KS (2019) Synthesis and characterization of novel imine substituted phthalocyanine for sensing of l-cysteine. J Electroanal Chem 834:130–137. https://doi.org/10.1016/j.jelechem.2018.12.050
Qi J, Zhang W, Cao R (2018) Solar-to-hydrogen energy conversion based on water splitting. Adv Energy Mater 8:1701620
Raptis D, Ploumistor A, Zogoraion E, Thamou E, Daleton M, Sygellon L, Tasis D, Lianos P (2018) Co-N doped reduced graphene oxide as oxygen reduction electrocatalyst applied to Photocatalytic Fuel Cells. Catal Today 315:31–35. https://doi.org/10.1016/j.cattod.2018.02.047
Rebekah A, Ashok KE, Viswanathan C, Ponpandian N (2020a) MnCo2O4 spinel anchored over rGO for enhancing the electrocatalytic activity towards oxygen evolution reaction (OER). Int J Hydrogen Energy 45:63916403. https://doi.org/10.1016/j.ijhydene.2019.12.164
Rebekah A, Anantharaj S, Viswanathan C, Ponpandian N (2020b) Zn-substituted MnCo2O4 nanostructure anchored over rGO for boosting the electrocatalytic performance towards methanol oxidation and oxygen evolution reaction (OER). Int J Hydrogen Energy 45:14713–14727. https://doi.org/10.1016/j.ijhydene.2020.03.231
Ren X, Wu T, Sun Y, Li Y, Xian G, Liu X, Shen C, Gracia J, Gao H, Yang H, Xu ZJ (2021) Spin-polarized oxygen evolution reaction under magnetic field. Nat Commun 12:2608. https://doi.org/10.1038/s41467-021-22865-y
Saha S, Ganguli AK (2017) FeCoNi Alloy as noble metal-free electrocatalyst for oxygen evolution reaction (OER). Chem Select 2:1630–1636. https://doi.org/10.1002/slct.201601243
Sonkar PK, Ganesan V, Gupta R, Yadav DK, Yadav M (2018) Nickel phthalocyanine integrated graphene architecture as bifunctional electrocatalyst for CO2 and O2 reductions. J Electrochem Chem 826:1–9. https://doi.org/10.1016/j.jelechem.2018.08.020
Tang J, Liang Z, Qin H, Liu X, Zhai B, Su Z, Liu Q, Lei H, Liu K, Zhao C, Cao R, Fang Y (2022) Large-area free-standing metalloporphyrin-based covalent organic framework films by liquid-air interfacial polymerization for oxygen electrocatalysis. Angew Chem Int Ed 135:e202214449. https://doi.org/10.1002/ange.202214449
Wang Z, Xiao S, Zhu Z, Long X, Zheng X, Lu X, Yang S (2015) Cobalt-embedded nitrogen doped carbon nanotubes: a bifunctional catalyst for oxygen electrode reactions in a wide pH range. Appl Mater Interfaces 7:4048–4055. https://doi.org/10.1021/am507744y
Wang H, Li Y, Wang R, He B, Gong Y (2018) Metal-organic-framework template-derived hierarchical porous CoP arrays for energy-saving overall water splitting. Electrochim Acta 284:504–512. https://doi.org/10.1016/j.electacta.2018.07.175
Wang X, Dou Y, Xie Y, Wang J, Xia T, Huo L, Zhao H (2020) A-site cation-ordering layered perovskite EuBa0.5Sr0.5Co2−xFexO5+δ as highly active and durable electrocatalysts for oxygen evolution reaction. ACS Omega 21:12501–12515. https://doi.org/10.1021/acsomega.0c01383
Wang D, Chang Y, Li Y, Zhang S, Xu S (2021) Well-dispersed NiCoS2 nanoparticles/rGO composite with a large specific surface area as an oxygen evolution reaction electrocatalyst. Rare Met. https://doi.org/10.1007/s12598-021-01733-0
Wang H, Zhang KHL, Hofmann JP, O’Shea VAd, Oropeza FE (2021a) The electronic structure of transition metal oxides for oxygen evolution reaction. J Mater Chem A 9:19465–19488. https://doi.org/10.1039/D1TA03732C
Wang D, Xu Y, Guo X, Fu Z, Yang Z, Sun W (2021b) Nickel foam as conductive substrate enhanced low-crystallinity two-dimensional iron hydrogen phosphate for oxygen evolution reaction. J Alloys Compd 870:159472. https://doi.org/10.1016/j.jallcom.2021.159472
Wu Z, Wang X, Huang J, Gao F (2018) Co-doped Ni–Fe mixed oxide mesoporous nanosheet array with low overpotential and high stability towards overall water splitting. J Mater Chem A 6:167–178. https://doi.org/10.1039/C7TA07956G
Wu X, Tang C, Cheng Y, Min X, Jiang SP, Wang S (2020) Bifunctional catalysts for reversible oxygen evolution reaction and oxygen reduction reaction: mix better. Chem A Eur J 26:3906–3929. https://doi.org/10.1002/chem.201905346
Xie L, Zhang X, Zhao B, Li P, Qi J, Guo X, Wang B, Lei H, Zhang W, Apfel U, Cao R (2021) Enzyme-inspired iron porphyrins for improved electrocatalytic oxygen reduction and evolution reactions. Angew Chem Int Ed 133:7654–7659. https://doi.org/10.1002/ange.202015478
Yadav RM, Wu J, Kochandra R, Ma L, Tiwary CS, Ge L, Ye G, Vajtai R, Lou J, Ajyan PM (2015) Carbon nitrogen nanotubes as efficient bifunctional electrocatalysts for oxygen reduction and evolution reactions. ACS Appl Mater Interfaces 22:11991–12000. https://doi.org/10.1021/acsami.5b02032
Yadav M, Sonkar PK, Prakash K, Ganesan V, Sankar M, Yadav DK, Gupta R (2020) Insight into efficient bifunctional catalysis: oxygen reduction and oxygen evolution reactions using MWCNTs based composites with 5,10,15,20-tetrakis(3′,5′-dimethoxyphenyl) porphyrinato cobalt(II) and 5,10,15,20- tetrakis(3′,5′-dihydroxyphenyl)porphyrinato cobalt(II). Int J Hydrog Energy 45:9710–9722. https://doi.org/10.1016/j.ijhydene.2020.01.224
Yang L, Ru F, Shi J, Yang T, Guo C, Chen Y, Wang E, Du Z, Chou K-C, Hou X (2023) Trifunctional electrocatalysts based on feather-like NiCoP 3D architecture for hydrogen evolution, oxygen evolution, and urea oxidation reactions. Ceram Int 49:659–668. https://doi.org/10.1016/j.ceramint.2022.09.035
Yanga L, Yanga T, Wanga E, Yua X, Wanga K, Dub Z, Cao S, Choua K-C, Houa X (2023) Bifunctional hierarchical NiCoP@FeNi LDH nanosheet array electrocatalyst for industrial-scale high-current-density water splitting. J Mater Sci Technol 159:33–40. https://doi.org/10.1016/j.jmst.2023.02.050
You B, Sun Y (2018) Innovative strategies for electrocatalytic water splitting. Acc Chem Res 51:1571–1580. https://doi.org/10.1021/acs.accounts.8b00002
Yue X, Jin Y, Shang PK (2017) Highly stable and efficient non-precious metal electrocatalysts of tantalum dioxyfluoride used for the oxygen evolution reaction. J Mater Chem A 5:8287–8291. https://doi.org/10.1039/C7TA01838J
Yuxiang Z, Yingjie Y, Tian X, Hao T, Yongpeng L, Zhuyin S, Ning Y, Xinlong T, Qi C (2021) Pyrimidine-functionalized covalent organic framework and its cobalt complex as an efficient electrocatalyst for oxygen evolution reaction. Chemsuschem 14(20):4556–4562. https://doi.org/10.1002/cssc.202101434
Zeng H, Oubla M, Zhong X, Alonso-Vante N, Du F, Xie Y, Huang Y, Ma J (2021) Rational defect and anion chemistries in Co3O4 for enhanced oxygen evolution reaction. Appl Catal B 281:119535. https://doi.org/10.1016/j.apcatb.2020.119535
Zeradjanin AR, Masa J, Spanos I, Schlögl R (2021) Activity and stability of oxides during oxygen evolution reaction from mechanistic controversies toward relevant electrocatalytic descriptors. Front Energy Res 8:613092. https://doi.org/10.3389/fenrg.2020.613092
Zhang Y, Cui B, Zhao C, Lin H, Li J (2013) Co–Ni layered double hydroxides for water oxidation in neutral electrolyte. Phys Chem Chem Phys 15:7363–7369. https://doi.org/10.1039/C3CP50202C
Zhang X, An L, Yin J, Xi P, Zhang Z, Du Y (2017) Effective Construction of high-quality iron oxy-hydroxides and co-doped iron oxy-hydroxides nanostructures: towards the promising oxygen evolution reaction application. Sci Rep 7:43590. https://doi.org/10.1038/srep43590
Zhang G, Liu B, Zhou H, Yang Y, Chen W, Zhao J (2018) Graphene wrapped phthalocyanine: enhanced oxidative desulfurization for dibenzothiophene in fuel. Appl Organomet Chem. https://doi.org/10.1002/aoc.4477
Zhang J, Li F, Chen W, Wang C, Cai D (2019) Facile synthesis of hollow co O-embedded carbon/reduced graphene oxides 3 4 nanocomposites for use as efficient electrocatalysts in oxygen evolution reaction. Electrochem Acta 300:123–130. https://doi.org/10.1016/j.electacta.2019.01.100
Zhao Z, Wu H, He H, Xu X, Jin Y (2014) A high-performance binary Ni–Co hydroxide-based water oxidation electrode with three-dimensional coaxial nanotube array structure. Adv Func Mater 24:4698–4705. https://doi.org/10.1002/adfm.201400118
Zhong W, Lin Z, Fang S, Wang D, Shen S, Zhang Q, Gu L, Wang Z, Fang B (2019) Improved oxygen evolution activity of IrO2 by in situ engineering of an ultra-small Ir sphere shell utilizing a pulsed laser. Nanoscale 11:4407–4413. https://doi.org/10.1039/C8NR10163A
Zhong X, Huang K, Zhang Y, Wang Y, Feng S (2021) Constructed interfacial oxygen-bridge chemical bonding in core-shell transition metal phosphides/carbon hybrid boosting oxygen evolution reaction. Chemsuschem 10:2141–2261. https://doi.org/10.1002/cssc.202100129
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One of the authors Chandrakala K.B. sincerely thanks the Department of Other Backward Class, Govt. of Karnataka for the fellowship and VGST GRD No.227, Govt of Karnataka for financial support.
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Chandrakala, K.B., Mruthyunjayachari, C.D., Shivaprasad, K.H. et al. Tetraether bridged benzylideneamino mercaptopropanoic acid substituted Cobalt phthalocyanine/rGO as a catalyst for oxygen evolution reaction in an alkaline medium. Chem. Pap. 78, 1167–1179 (2024). https://doi.org/10.1007/s11696-023-03155-x
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DOI: https://doi.org/10.1007/s11696-023-03155-x