Highly Electro-Conductive Thiophene and N-methylpyrrole functionalized hyperbranched polypropylenimine tetramine-co-poly(3-hexylthiophene-2,5-diyl) donor materials for organic solar cells

Morongwa E. Ramoroka1, Sodiq T. Yussuf2, Kelechi C. Nwambaekwe2, Miranda M. Ndipingwi2, Vivian S. John-Denk2, Kwena D. Modibane3, Emmanuel I. Iwuoha2, Samantha F. Douman1
1Department of Chemistry, University of Cape Town, Rondebosch, 7707, Cape Town, South Africa
2SensorLab, Department of Chemistry, University of the Western Cape, 4th Floor Chemical Sciences Building, Bellville 7535, Cape Town, South Africa
3Nanotechnology Research Lab, Department of Chemistry, School of Physical and Mineral Sciences, University of Limpopo (Turfloop), Polokwane, Sovenga 0727, South Africa

Tài liệu tham khảo

Dipta, 2022, Estimating the potential for semitransparent organic solar cells in agrophotovoltaic greenhouses, Appl. Energy, 328 Mahmoudi, 2022, Near ultra-violet absorbers for transparent organic solar cells, Dyes Pigments, 207, 10.1016/j.dyepig.2022.110752 Kumar, 2023, Solar energy: a promising renewable source for meeting energy demand in Indian agriculture applications, Sustain. Energy Technol. Assessments, 55 Motlagh, 2023, Integrated value model for sustainability assessment of residential solar energy systems towards minimizing urban air pollution in Tehran, Sol. Energy, 249, 40, 10.1016/j.solener.2022.10.047 Al-Buraiki, 2023, Influence of load coordination with solar energy potential on the optimal sizing of standalone PV systems, Energy Convers. Manag. X, 17 Yao, 2022, Recent advances in single-junction organic solar cells, Angew. Chem., 134, 10.1002/ange.202209021 Yussuf, 2023, Novel heterojunction superstrate Cu2ZnInS4−x (CZIS) thin film kesterite solar cell with vertical arrays of hexagonal ZnO nanorods window layer, J. Alloys Compd., 935, 10.1016/j.jallcom.2022.168211 Nwambaekwe, 2023, Enhanced photovoltaic effects of microwave-assisted polyol-synthesized Cu2(Pd/Zn)SnS4 kesterite nanoparticles, J. Sci.: Adv. Mater. Dev., 8 Deo, 2023, Tweaking the performance of thin film CIGS solar cell using InP as buffer layer, Optik, 273, 10.1016/j.ijleo.2022.170357 Thiesbrummel, 2023, Understanding and minimizing VOC losses in all-perovskite tandem photovoltaics, Adv. Energy Mater., 13, 10.1002/aenm.202202674 Zhang, 2023, Recent advances of non-fullerene organic solar cells: from materials and morphology to devices and applications, EcoMat, 5, 10.1002/eom2.12281 Liu, 2023, Self-doping n-type polymer as cathode interface layer enables efficient organic solar cells, Opt. Mater., 135, 10.1016/j.optmat.2022.113288 Mdluli, 2022, π-Conjugated polymers and their application in organic and hybrid organic-silicon solar cells, Polymers, 14, 716, 10.3390/polym14040716 Rafiq, 2022, End-capped modification of dithienosilole based small donor molecules for high performance organic solar cells using DFT approach, J. Mol. Liq., 345, 10.1016/j.molliq.2021.118138 Djoumessi Yonkeu, 2022, Microscopic, spectroscopic, and electrochemical characterization of novel semicrystalline poly (3-hexylthiophene)-based dendritic star copolymer, Polymers, 14, 4400, 10.3390/polym14204400 Mehboob, 2022, In silico modelling of acceptor materials by end-capped and π-linker modifications for high-performance organic solar cells: estimated PCE> 18, Comput. Theor. Chem., 1208 Mehboob, 2022, Impact of π-linker modifications on the photovoltaic performance of rainbow-shaped acceptor molecules for high performance organic solar cell applications, Phys. B Condens. Matter, 625, 10.1016/j.physb.2021.413465 Suresh, 2022, Low-cost synthesis and characterization of donor P3HT polymer for fabrication of organic solar cell, In IOP Conf. Ser. Mater. Sci. Eng., 1221 Oliveira, 2013, Effect of chemical modifications on the electronic structure of poly (3-hexylthiophene), J. Polym. Sci. B Polym. Phys., 51, 842, 10.1002/polb.23274 Chevrier, 2019, Synthesis and properties of a P3HT-based ABA triblock copolymer containing a perfluoropolyether central segment, Synth. Met., 252, 127, 10.1016/j.synthmet.2019.04.001 Ansari, 2022, Molecular tailoring of donor and acceptor materials of organic solar cells for improvement of their optoelectronic properties, Mater. Sci. Semicond. Process., 150, 10.1016/j.mssp.2022.106919 Kuila, 2010, Soluble P3HT-grafted carbon nanotubes: synthesis and photovoltaic application, Macromolecules, 43, 6699, 10.1021/ma100917p Fukushima, 2019, Synthesis and characterization of cyclic P3HT as a donor polymer for organic solar cells, J. Polym. Sci. B Polym. Phys., 57, 266, 10.1002/polb.24779 Li, 2023, The dynamics of delocalized excitations in organic solar cells with nonfullerene acceptors, J. Phys. Chem. Lett., 14, 3031, 10.1021/acs.jpclett.2c03911 Zhu, 2021, A quinoxaline-based D–A copolymer donor achieving 17.62% efficiency of organic solar cells, Adv. Mater., 33, 10.1002/adma.202100474 Bi, 2023, Enhancing photon utilization efficiency for high-performance organic photovoltaic cells via regulating phase-transition kinetics, Adv. Mater., 35, 10.1002/adma.202210865 Fischer, 2009, Core-functionalized dendritic oligothiophenes—novel donor–acceptor systems, J. Mater. Chem., 19, 4784, 10.1039/b904243a Sun, 2023, Preparation of DA copolymers based on dithiazologermole and germaindacenodithiazole as weak electron donor units, Polym. J., 55, 797, 10.1038/s41428-023-00771-y Xu, 2023, Sequential deposition of multicomponent bulk heterojunctions increases efficiency of organic solar cells, Adv. Mater., 35 Tang, 2019, Benzotriazole-based acceptor and donors, coupled with chlorination, achieve a high VOC of 1.24 V and an efficiency of 10.5% in fullerene-free organic solar cells, Chem. Mater., 31, 3941, 10.1021/acs.chemmater.8b05316 Ashraf, 2006, Synthesis and properties of fluorene-based polyheteroarylenes for photovoltaic devices, J. Polym. Sci. Polym. Chem., 44, 6952, 10.1002/pola.21645 Koeppe, 2005, Complexation of pyrrolidinofullerenes and zinc-phthalocyanine in a bilayer organic solar cell structure, Appl. Phys. Lett., 87, 10.1063/1.2146070 Winder, 2002, Sensitization of low bandgap polymer bulk heterojunction solar cells, Thin Solid Films, 403, 373, 10.1016/S0040-6090(01)01588-7 Zhang, 2010, Bulk-heterojunction solar cells with benzotriazole-based copolymers as electron donors: largely improved photovoltaic parameters by using PFN/Al bilayer cathode, Macromolecules, 43, 9771, 10.1021/ma102080c Sun, 2018, A low cost and high-performance polymer donor material for polymer solar cells, Nat. Commun., 9, 743, 10.1038/s41467-018-03207-x Zhang, 2023, Regulating intramolecular charge transfer and resonance effects to realize ultrawide bandgap conjugated polymer for high-performance all-polymer solar cells, Adv. Funct. Mater. Wang, 2023, Organic photovoltaic cells offer ultrahigh VOC of∼ 1.2 V under AM 1.5 G light and a high efficiency of 21.2% under indoor light, Chem. Eng. J., 451, 10.1016/j.cej.2022.139080 Wang, 2020, Tuning the intermolecular interaction of A2-A1-D-A1-A2 type non-fullerene acceptors by substituent engineering for organic solar cells with ultrahigh Voc of ∼ 1.2 V, Sci. China Chem., 63, 1666, 10.1007/s11426-020-9840-x Gao, 2022, Thermally stable poly (3-hexylthiophene): nonfullerene solar cells with efficiency breaking 10, Aggregate, 3, e190, 10.1002/agt2.190 Ma, 2011, Conjugated dendritic oligothiophenes for solution-processed bulk heterojunction solar cells, Front. Optoelectron. China, 4, 12, 10.1007/s12200-011-0206-1 Memela, 2020, Electro-photovoltaics of polymer-stabilized copper–indium selenide quantum dot, Electroanalysis, 32, 3086, 10.1002/elan.202060392 Ramoroka, 2020, Synthesis and photovoltaics of novel 2, 3, 4, 5-tetrathienylthiophene-co-poly (3-hexylthiophene-2, 5-diyl) donor polymer for organic solar cell, Polymers, 13, 2, 10.3390/polym13010002 Ramoroka, 2022, Synthesis and reactivities of conducting hexathienylbenzene-co-poly (3-hexylthiophene) star-branched copolymer as donor material for organic photovoltaic cell, Front. Mater., 9, 10.3389/fmats.2022.856008 Kesornsit, 2022, Synthesis of highly conductive poly (3-hexylthiophene) by chemical oxidative polymerization using surfactant templates, Polymers, 14, 3860, 10.3390/polym14183860 Ansari, 2018, Synthesis and characterization of poly (3-hexylthiophene): improvement of regioregularity and energy band gap, RSC Adv., 8, 8319, 10.1039/C8RA00555A Dattani, 2015, Rapid precipitation: an alternative to solvent casting for organic solar cells, ChemPhysChem, 16, 1231, 10.1002/cphc.201402758 Saini, 2012, Structural and optoelectronic properties of P3HT-graphene composites prepared by in situ oxidative polymerization, J. Appl. Phys., 112, 10.1063/1.4751271 Rassie, 2015, Microscopy and electroanalysis of a first-generation copper-poly (propyleneimine) metallodendrimer system, Int. J. Electrochem. Sci., 10, 432, 10.1016/S1452-3981(23)05003-4 Arjomandi, 2013, A spectroelectrochemical study of conducting pyrrole-N-methylpyrrole copolymers in nonaqueous solution, J. Solid State Electrochem., 17, 1881, 10.1007/s10008-013-2114-3 Wang, 1995, Poly (3, 4-ethylenedithiathiophene). A new soluble conductive polythiophene derivative, Chem. Mater., 7, 58, 10.1021/cm00049a011 Singh, 2021, CdSe nanorod-reinforced poly (thiophene) composites in designing energy storage devices: study of morphology and dielectric behavior, Polym. Bull., 78, 115, 10.1007/s00289-020-03104-8 Chen, 1995, Regiocontrolled synthesis of poly (3-alkylthiophenes) mediated by Rieke zinc: their characterization and solid-state properties, J. Am. Chem. Soc., 117, 233, 10.1021/ja00106a027 Shokry, 2022, Supercapacitor based on polymeric binary composite of polythiophene and single-walled carbon nanotubes, Sci. Rep., 12, 10.1038/s41598-022-15477-z John, 2017, Poly [(arylene ethynylene)-alt-(arylene vinylene)] s based on anthanthrone and its derivatives: synthesis and photophysical, electrochemical, electroluminescent, and photovoltaic properties, Macromolecules, 50, 8357, 10.1021/acs.macromol.7b02136 Taukeer Khan, 2021, In-Situ growth of cadmium telluride nanocrystals in poly (3-hexylthiophene) matrix for photovoltaic application, J. Appl. Phys., 110 Samanta, 2011, Interactions between acidic crude oil and alkali and their effects on enhanced oil recovery, Energy Fuel., 25, 1642, 10.1021/ef101729f Arvas, 2023, Hydrothermal synthesis of polypyrrole/dye-functionalized carbon cloth electrode for wide potential window supercapacitor, Synth. Met., 293, 10.1016/j.synthmet.2022.117275 Sato, 2021, Fourier transform infrared absorption (FTIR) on dry stratum corneum, corneocyte-lipid interfaces: experimental and vibrational spectroscopy calculations, Spectrochim. Acta Mol. Biomol. Spectrosc., 249, 10.1016/j.saa.2020.119218 Agrawal, 2013, Synthesis of CdS nanocrystals in poly (3-hexylthiophene) polymer matrix: optical and structural studies, J. Nanoparticle Res., 15, 1, 10.1007/s11051-013-1697-z Bo, 2020, Cardanol derived P, Si and N based precursors to develop flame retardant phenolic foam, Sci. Rep., 10, 1, 10.1038/s41598-020-68910-6 Garcia-Carvajal, 2022, Effect of incorporating iron II disulfide to poly (3-hexylthiophene-2, 5-diyl) on its physicochemical properties and influence in photovoltaic devices, Polym. Bull., 1 Altarawneh, 2020, Synthesis, characterization, thermodynamics and thermal degradation kinetics of imine-linked polymers, J. Polym. Res., 27, 1, 10.1007/s10965-020-02317-9 Rahimi, 2014, Light absorption of poly (3-hexylthiophene) single crystals, RSC Adv., 4, 11121, 10.1039/C3RA47064D Zhu, 2023, Meniscus-Assisted solution printing enables cocrystallization in poly (3-alkylthiophene)-based blends for field-effect transistors, Chin. J. Polym. Sci., 1 Fei, 2015, Influence of backbone fluorination in regioregular poly (3-alkyl-4-fluoro) thiophenes, J. Am. Chem. Soc., 137, 6866, 10.1021/jacs.5b02785 Yoshinaga, 2021, Glycothermally synthesized carbon dots with narrow-bandwidth and color-tunable solvatochromic fluorescence for wide-color-gamut displays, ACS Omega, 6, 1741, 10.1021/acsomega.0c05993 Nagai, 2013, Effect of molecular weight and conformation on photoluminescence quantum yield of fluorene/poly (2-methoxy-5-(2′-ethylhexyloxy)-1, 4-phenylene vinylene)(MEH− PPV) copolymers, ECS J. Solid State Sci. Technol., 2, R218, 10.1149/2.045309jss Casey, 2014, Thioalkyl-substituted benzothiadiazole acceptors: copolymerization with carbazole affords polymers with large Stokes shifts and high solar cell voltages, Macromolecules, 47, 2279, 10.1021/ma5000943 Ma, 2012, Large Stokes shift chiral polymers containing (R, R)-salen-based binuclear boron complex: synthesis, characterization, and fluorescence properties, Polymer, 53, 3894, 10.1016/j.polymer.2012.07.003 Moia, 2019, Design and evaluation of conjugated polymers with polar side chains as electrode materials for electrochemical energy storage in aqueous electrolytes, Energy Environ. Sci., 12, 1349, 10.1039/C8EE03518K Szumska, 2021, Reversible electrochemical charging of n-type conjugated polymer electrodes in aqueous electrolytes, J. Am. Chem. Soc., 143, 14795, 10.1021/jacs.1c06713 Zhang, 2019, Conjugation-broken thiophene-based electropolymerized polymers with well-defined structures: effect of conjugation lengths on electrochromic properties, Phys. Chem. Chem. Phys., 21, 24092, 10.1039/C9CP04308J Keshtov, 2023, Single junction binary and ternary polymer solar cells-based D–A structured copolymer with low lying HOMO energy level and two nonfullerene acceptors, Mol. Syst. Design Eng., 8, 53, 10.1039/D2ME00166G Bruchlos, 2018, Poly (3-hexylthiophene) revisited–Influence of film deposition on the electrochemical behaviour and energy levels, Electrochim. Acta, 269, 299, 10.1016/j.electacta.2018.02.126 Li, 2020, Enhanced proton conductivity of imidazole-doped thiophene-based covalent organic frameworks via subtle hydrogen bonding modulation, ACS Appl. Mater. Interfaces, 12, 22910, 10.1021/acsami.0c04002 Cui, 2012, In situ synthesized heteropoly acid/polyaniline/graphene nanocomposites to simultaneously boost both double layer-and pseudo-capacitance for supercapacitors, Phys. Chem. Chem. Phys., 14, 12823, 10.1039/c2cp42022h Chandel, 2019, Ag–Ni nanoparticle anchored reduced graphene oxide nanocomposite as advanced electrode material for supercapacitor application, ACS Appl. Electr. Mater., 1, 1215, 10.1021/acsaelm.9b00194 Gong, 2012, In situ growth of Co0.85Se and Ni0.85Se on conductive substrates as high-performance counter electrodes for dye-sensitized solar cells, J. Am. Chem. Soc., 134, 10953, 10.1021/ja303034w Agee, 2023, Electrochemical characterization of biomolecular electron transfer at conductive polymer interfaces, J. Electrochem. Soc., 170, 10.1149/1945-7111/acb239 Wen, 2016, Photoelectrochemical properties of CuS-GeO2-TiO2 composite coating electrode, PLoS One, 11, 10.1371/journal.pone.0152862 Sharma, 2014, Triazine-bridged porphyrin triad as electron donor for solution-processed bulk hetero-junction organic solar cells, J. Phys. Chem. C, 118, 5968, 10.1021/jp500090h Yurtdaş, 2023, Vapor deposition of poly (hexafluorobutyl acrylate) nanocoating for encapsulation of organic solar cells, Prog. Org. Coating, 177, 10.1016/j.porgcoat.2023.107443 Hu, 2023, Raman spectroelectrochemical study on the effect of solvent processing on the active layer morphology of polymer solar cells, Chem. Phys., 564, 10.1016/j.chemphys.2022.111700 Li, 2012, Origin of the efficiency improvement in pre-annealed P3HT/PCBM solar cells with LiF/Al electrodes, Chem. Phys. Lett., 553, 36, 10.1016/j.cplett.2012.10.006 Yuan, 2020, Improved stability in P3HT: PCBM photovoltaics by incorporation of well-designed polythiophene/graphene compositions, Polym. Int., 69, 833, 10.1002/pi.6024 Yuan, 2023, Extending the absorption spectra and enhancing the charge extraction by the organic bulk heterojunction for CsPbBr3 perovskite solar cells, ACS Sustain. Chem. Eng., 11, 718, 10.1021/acssuschemeng.2c05859 Matejovsky, 2017, Study of corrosion of metallic materials in ethanol–gasoline blends: application of electrochemical methods, Energy Fuel., 31, 10880, 10.1021/acs.energyfuels.7b01682 Daubert, 2017, Corrosion protection of copper using Al2O3, TiO2, ZnO, HfO2, and ZrO2 atomic layer deposition, ACS Appl. Mater. Interfaces, 9, 4192, 10.1021/acsami.6b13571