Pillararene/Calixarene-based systems for battery and supercapacitor applications

Lehn, 1993, Supramolecular chemistry, Science, 260, 1762, 10.1126/science.8511582 Cram, 1978, Design of complexes between synthetic hosts and organic guests, Acc. Chem. Res., 11, 8, 10.1021/ar50121a002 Pedersen, 1972, Macrocyclic polyethers: dibenzo-18-crown-6 polyether and dicyclohexyl-18-crown-6 polyether, Org. Synth., 52, 66, 10.15227/orgsyn.052.0066 Xing, 2018, Controlling supramolecular chirality in multicomponent self-assembled systems, Acc. Chem. Res., 51, 2324, 10.1021/acs.accounts.8b00312 Jones, 2019, Braiding, branching and chiral amplification of nanofibres in supramolecular gels, Nat. Chem., 11, 375, 10.1038/s41557-019-0222-0 Ogoshi, 2019, Applications of pillar[n]arene-based supramolecular assemblies, Angew. Chem. Int. Ed., 58, 2197, 10.1002/anie.201805884 Wang, 2020, Role of functionalized pillararene architectures in supramolecular catalysis, Angew. Chem. Int. Ed., 60, 9205, 10.1002/anie.202010150 Morimoto, 2020, Advances in supramolecular host-mediated reactivity, Nat. Catal., 3, 969, 10.1038/s41929-020-00528-3 Cheng, 2015, Cathodic voltammetric behavior of pillar[5]quinone in nonaqueous media. Symmetry effects on the electron uptake sequence, J. Am. Chem. Soc., 137, 9788, 10.1021/jacs.5b05546 Tovar, 2010, Electrochemistry of functional supramolecular systems, J. Am. Chem. Soc., 132, 9511, 10.1021/ja104428n Evtyugin, 2020, Electrochemical sensors and biosensors on the pillar[5]arene platform, Russ. Chem. Bull., 69, 859, 10.1007/s11172-020-2843-2 Zhang, 2021, Intrinsically porous molecular materials (IPMs) for natural gas and benzene derivatives separations, Acc. Chem. Res., 54, 155, 10.1021/acs.accounts.0c00582 Cao, 2009, A facile and efficient preparation of pillararenes and a pillarquinone, Angew. Chem. Int. Ed., 48, 9721, 10.1002/anie.200904765 Wu, 2018, Desymmetrized leaning pillar[6]arene, Angew. Chem. Int. Ed., 57, 9853, 10.1002/anie.201805980 Cao, 2014, Pillar[n]arenes - a novel, highly promising class of macrocyclic host molecules, Asian J. Org. Chem., 3, 244, 10.1002/ajoc.201300224 Song, 2018, Molecular-scale porous materials based on pillar[n]arenes, Chem, 4, 2029, 10.1016/j.chempr.2018.05.015 Feng, 2021, Molecular pumps and motors, J. Am. Chem. Soc., 143, 5569, 10.1021/jacs.0c13388 Ogoshi, 2008, para-Bridged symmetrical pillar[5]arenes: their Lewis acid catalyzed synthesis and host-guest property, J. Am. Chem. Soc., 130, 5022, 10.1021/ja711260m Shetty, 2018, Making pillar[6]arenes to lean: an art of tuning a supramolecular host, Sci. China Chem., 62, 289, 10.1007/s11426-018-9362-0 Ogoshi, 2016, Pillar-shaped macrocyclic hosts pillar[n]arenes: new key players for supramolecular chemistry, Chem. Rev., 116, 7937, 10.1021/acs.chemrev.5b00765 Deng, 2020, Supramolecular hosts as in vivo sequestration agents for pharmaceuticals and toxins, Chem. Soc. Rev., 49, 7516, 10.1039/D0CS00454E Fa, 2020, Sequential chiral induction and regulator-assisted chiral memory of pillar[5]arenes, Angew. Chem. Int. Ed., 59, 20353, 10.1002/anie.202010050 Zhu, 2020, Pillararene host-guest complexation induced chirality amplification: a new way to detect cryptochiral compounds, Angew. Chem. Int. Ed., 59, 10868, 10.1002/anie.202001680 Strutt, 2014, Functionalizing pillar[n]arenes, Acc. Chem. Res., 47, 2631, 10.1021/ar500177d Zhou, 2020, Supramolecular-macrocycle-based crystalline organic materials, Adv. Mater., 32 Jie, 2018, Nonporous adaptive crystals of pillararenes, Acc. Chem. Res., 51, 2064, 10.1021/acs.accounts.8b00255 Kakuta, 2018, Stimuli-responsive supramolecular assemblies constructed from pillar[n]arenes, Acc. Chem. Res., 51, 1656, 10.1021/acs.accounts.8b00157 Chen, 2019, Functionalization of inorganic nanomaterials with pillar[n]arenes, Chem. Commun., 55, 6817, 10.1039/C9CC03165K Xia, 2020, Functional supramolecular polymeric networks: the marriage of covalent polymers and macrocycle-based host-guest interactions, Chem. Rev., 120, 6070, 10.1021/acs.chemrev.9b00839 Hua, 2018, Supramolecular solid-state microlaser constructed from pillar[5]arene-based host-guest complex microcrystals, J. Am. Chem. Soc., 140, 15651, 10.1021/jacs.8b11156 Lao, 2011, A computational study of unique properties of pillar[n]quinones: self-assembly to tubular structures and potential applications as electron acceptors and anion recognizers, J. Comput. Chem., 32, 2716, 10.1002/jcc.21853 Xie, 2021, Heteroatom-bridged pillar[4]quinone: evolutionary active cathode material for lithium-ion battery using density functional theory, J. Chem. Sci., 133, 2, 10.1007/s12039-020-01863-5 Petrushenko, 2021, Hydrogen adsorption on pillar[6]arene: a computational study, Phys. E, 130, 10.1016/j.physe.2021.114719 Yao, 2017, Supramolecular host-guest system as ratiometric Fe3+ ion sensor based on water-soluble pillar[5]arene, ACS Appl. Mater. Interfaces, 9, 36320, 10.1021/acsami.7b12063 Rashvand Avei, 2020, Visualization and quantitation of electronic communication pathways in a series of redox-active pillar[6]arene-based macrocycles, Commun. Chem., 3, 117, 10.1038/s42004-020-00363-4 Avei, 2017, Through-space communication effects on the electrochemical reduction of partially oxidized pillar[5]arenes containing variable numbers of quinone units, J. Org. Chem., 82, 8590, 10.1021/acs.joc.7b01366 Zhang, 2020, Recent progress in calix[n]quinone (n = 4, 6) and pillar[5]quinone electrodes for secondary rechargeable batteries, Batter. Supercaps., 3, 476, 10.1002/batt.202000038 Huan, 2017, Computational electrochemistry of pillar[5]quinone cathode material for lithium-ion batteries, Comp. Mater. Sci., 137, 233, 10.1016/j.commatsci.2017.05.045 Huan, 2017, Theoretical investigation of pillar[4]quinone as a cathode active material for lithium-ion batteries, J. Mol. Model., 23, 105, 10.1007/s00894-017-3282-3 Ran, 2020, Pillar[6]arene@AuNPs functionalized N-CQDs@Co3O4 hybrid composite for ultrasensitive electrochemical detection of human epididymis protein 4, ACS Sustain. Chem. Eng., 8, 10161, 10.1021/acssuschemeng.0c02238 Cao, 2021, Pillararene-based self-assemblies for electrochemical biosensors, Biosens. Bioelectron., 181, 113, 10.1016/j.bios.2021.113164 Ye, 2015, Supramolecule-mediated synthesis of MoS2/reduced graphene oxide composites with enhanced electrochemical performance for reversible lithium storage, J. Mater. Chem. A, 3, 6884, 10.1039/C5TA00006H Guo, 2020, One-pot synthesis of hydrazide-pillar[5]arene functionalized reduced graphene oxide for supercapacitor electrode, Chem. Eng. J., 391, 10.1016/j.cej.2019.123511 Xiong, 2019, Pillar[5]quinone-carbon nanocomposites as high-capacity cathodes for sodium-ion batteries, Chem. Mater., 31, 8069, 10.1021/acs.chemmater.9b02601 Yu, 2017, Fabrication of few-layer molybdenum disulfide/reduced graphene oxide hybrids with enhanced lithium storage performance through a supramolecule-mediated hydrothermal route, Carbon, 114, 125, 10.1016/j.carbon.2016.12.002 Tarascon, 2001, Issues and challenges facing rechargeable lithium batteries, Nature, 414, 359, 10.1038/35104644 Seeman, 2020, The mutation of the “Nobel Prize in Chemistry” into the “Nobel Prize in Chemistry or Life Sciences”: several decades of transparent and opaque evidence of change within the Nobel Prize program, Angew. Chem. Int. Ed., 59, 2942, 10.1002/anie.201906266 Zhu, 2019, Conjugated carbonyl compounds as high-performance cathode materials for rechargeable batteries, Chem. Mater., 31, 8582, 10.1021/acs.chemmater.9b03109 Tie, 2020, Design strategies for high-performance aqueous Zn/organic batteries, Angew. Chem. Int. Ed., 59, 21293, 10.1002/anie.202008960 Zhao, 2018, High-capacity aqueous zinc batteries using sustainable quinone electrodes, Sci. Adv., 4, eaao1761, 10.1126/sciadv.aao1761 Xu, 2021, The progress and prospect of tunable organic molecules for organic lithium-ion batteries, ACS Nano, 15, 47, 10.1021/acsnano.0c05896 Lu, 2020, Prospects of organic electrode materials for practical lithium batteries, Nat. Rev. Chem., 4, 127, 10.1038/s41570-020-0160-9 Parker, 2017, Rechargeable nickel-3D zinc batteries: an energy-dense, safer alternative to lithium-ion, Science, 356, 415, 10.1126/science.aak9991 Li, 2021, Continuous electrical pumping membrane process for seawater lithium mining, Energy Environ. Sci., 14, 3152, 10.1039/D1EE00354B He, 2020, Mining lithium from seawater, Joule, 4, 1357, 10.1016/j.joule.2020.06.015 Zhang, 2019, Calixarene-functionalized porous carbon aerogels for polysulfide capture: cathodes for high performance lithium-sulfur batteries, ChemPlusChem, 84, 1709, 10.1002/cplu.201900554 Poizot, 2020, Opportunities and challenges for organic electrodes in electrochemical energy storage, Chem. Rev., 120, 6490, 10.1021/acs.chemrev.9b00482 Williams, 1969, A high energy density lithium/dichloroisocyanuric acid battery system, J. Electrochem. Soc., 116, 2, 10.1149/1.2411755 Alto, 1972, Investigation into the use of quinone compounds for battery cathodes, Electrochim. Acta, 17, 873, 10.1016/0013-4686(72)90010-2 Ravet, 1998, Novel cathode materials based on organic couples for lithium batteries, Mater. Res. Soc. Symp. Proc., 496, 263, 10.1557/PROC-496-263 Reddy, 1993, Calixarenes. 32. Reactions of calix[4]quinones, J. Org. Chem., 58, 3245, 10.1021/jo00064a009 Gomezkaifer, 1994, Electroactive calixarenes. 1. Properties of calixquinones redox and cation-binding, J. Am. Chem. Soc., 116, 3580, 10.1021/ja00087a051 Huang, 2020, Synthesis and application of calix[6]quinone as a high-capacity organic cathode for plastic crystal electrolyte-based lithium-ion batteries, Energy Storage Mater., 26, 465, 10.1016/j.ensm.2019.11.020 Ahmad, 2017, A hierarchically porous hypercrosslinked and novel quinone based stable organic polymer electrode for lithium-ion batteries, Electrochim. Acta, 255, 145, 10.1016/j.electacta.2017.09.017 Zhu, 2014, All-solid-state lithium organic battery with composite polymer electrolyte and pillar[5]quinone cathode, J. Am. Chem. Soc., 136, 16461, 10.1021/ja507852t Yan, 2019, High-capacity organic sodium ion batteries using a sustainable C4Q/CMK-3/SWCNT electrode, Inorg. Chem. Front., 6, 1977, 10.1039/C9QI00507B Yang, 2020, Holey graphite: a promising anode material with ultrahigh storage for lithium-ion battery, Electrochim. Acta, 346, 10.1016/j.electacta.2020.136244 Yang, 2003, Performance of LiFePO4 as lithium battery cathode and comparison with manganese and vanadium oxides, J. Power Sources, 119121, 239, 10.1016/S0378-7753(03)00240-4 Feng, 2016, Nanostructured palladium catalyst poisoning depressed by cobalt phosphide in the electro-oxidation of formic acid for fuel cells, Nano Energy, 30, 355, 10.1016/j.nanoen.2016.10.023 Yao, 2010, High-capacity organic positive-electrode material based on a benzoquinone derivative for use in rechargeable lithium batteries, J. Power Sources, 195, 8336, 10.1016/j.jpowsour.2010.06.069 Huang, 2013, Quasi-solid-state rechargeable lithium-ion batteries with a calix[4]quinone cathode and gel polymer electrolyte, Angew. Chem. Int. Ed., 52, 9162, 10.1002/anie.201302586 Hirohata, 2021, Pillar[6]quinone: facile synthesis, crystal structures and electrochemical properties, Chem. Commun., 57, 6360, 10.1039/D1CC02413B Zhang, 2021, Characterization methods of organic electrode materials, J. Energy Chem., 57, 291, 10.1016/j.jechem.2020.08.054 Yu, 2017, Fabrication of MoS2/reduced graphene oxide hybrid as an earth-abundant hydrogen evolution electrocatalyst, Mater. Lett., 188, 48, 10.1016/j.matlet.2016.10.088 Xiao, 2021, Recent advances in electrocatalysts for proton exchange membrane fuel cells and alkaline membrane fuel cells, Adv. Mater., 10.1002/adma.202006292 Zhang, 2020, Advancing proton exchange membrane electrolyzers with molecular catalysts, Joule, 4, 1408, 10.1016/j.joule.2020.06.001 Shen, 2015, Novel sulfonated Nafion®-based composite membranes with pillararene as selective artificial proton channels for application in direct methanol fuel cells, Int. J. Hydrogen Energy, 40, 13071, 10.1016/j.ijhydene.2015.07.073 Ogoshi, 2016, Spherical vesicles formed by co-assembly of cyclic pentagonal pillar[5]quinone with cyclic hexagonal pillar[6]arene, J. Am. Chem. Soc., 138, 8064, 10.1021/jacs.6b04125 Kiruthika, 2020, Anion-responsive pseudo[3]rotaxane from a difunctionalized pillar[4]arene[1]quinone and a bis-imidazolium cation, Org. Lett., 22, 7831, 10.1021/acs.orglett.0c02710 Wu, 2015, Designing high-voltage carbonyl-containing polycyclic aromatic hydrocarbon cathode materials for Li-ion batteries guided by Clar’s theory, J. Mater. Chem. A, 3, 19137, 10.1039/C5TA05437K Sola, 2013, Forty years of Clar’s aromatic π-sextet rule, Front. Chem., 1, 22, 10.3389/fchem.2013.00022 Zhao, 2019, Theoretical study on lithiation mechanism of benzoquinonebased macrocyclic compounds as cathode for lithium-ion batteries, Phys. Chem. Chem. Phys., 21, 11004, 10.1039/C9CP00403C Sri Devi Kumari, 2016, A kish graphitic lithium-insertion anode material obtained from non-biodegradable plastic waste, Energy, 95, 483, 10.1016/j.energy.2015.11.069 Lei, 2018, A solution-processed pillar[5]arene-based small molecule cathode buffer layer for efficient planar perovskite solar cells, Nanoscale, 10, 8088, 10.1039/C8NR00898A Li, 2018, A high-performance sodium-ion hybrid capacitor constructed by metal-organic framework-derived anode and cathode materials, Adv. Funct. Mater., 28 Genorio, 2010, Electroactive organic molecules immobilized onto solid nanoparticles as a cathode material for lithium-ion batteries, Angew. Chem. Int. Ed., 49, 7222, 10.1002/anie.201001539 Liao, 2021, Conjugating pillararene dye in dye-sensitized solar cells, Cell Rep. Phys. Sci., 2 Chen, 2021, Spectroscopic insight into efficient and stable hole transfer at the perovskite/spiro-OMeTAD interface with alternative additives, ACS Appl. Mater. Interfaces, 13, 5752, 10.1021/acsami.0c19111 Shibayama, 2020, Control of molecular orientation of spiro-OMeTAD on substrates, ACS Appl. Mater. Interfaces, 12, 50187, 10.1021/acsami.0c15509 Jena, 2017, Severe morphological deformation of spiro-OMeTAD in (CH3NH3)PbI3 solar cells at high temperature, ACS Energy Lett., 2, 1760, 10.1021/acsenergylett.7b00582 Bettucci, 2021, Dendritic-like molecules built on a pillar[5]arene core as hole transporting materials for perovskite solar cells, Chem. Eur. J., 27, 8110, 10.1002/chem.202101110 Waghmode, 2017, Calixarene based nanocomposite materials for high-performance supercapacitor electrode, New J. Chem., 41, 9752, 10.1039/C7NJ01125C Hu, 2013, Recent progress in high-voltage lithium ion batteries, J. Power Sources, 237, 229, 10.1016/j.jpowsour.2013.03.024 Choi, 2016, Promise and reality of post-lithium-ion batteries with high energy densities, Nat. Rev. Mater., 1, 16013, 10.1038/natrevmats.2016.13 Gu, 2019, Tunable redox chemistry and stability of radical intermediates in 2D covalent organic frameworks for high performance sodium ion batteries, J. Am. Chem. Soc., 141, 9623, 10.1021/jacs.9b03467 Zhang, 2014, Inorganic & organic materials for rechargeable Li batteries with multi-electron reaction, Sci. China Mater., 57, 42, 10.1007/s40843-014-0006-0 Li, 2021, High-energy-density quinone-based electrodes with [Al(OTF)]2+ storage mechanism for rechargeable aqueous aluminum batteries, Adv. Funct. Mater., 31 Yang, 2017, Fluorescent supramolecular polymers based on pillar[5]arene for OLED device fabrication, ACS Macro Lett., 6, 647, 10.1021/acsmacrolett.7b00309 Murray, 2017, The aqueous supramolecular chemistry of cucurbit[n]urils, pillar[n]arenes and deep-cavity cavitands, Chem. Soc. Rev., 46, 2479, 10.1039/C7CS00095B Zhang, 2018, Pillararene-based self-assembled amphiphiles, Chem. Soc. Rev., 47, 5491, 10.1039/C8CS00037A Hang, 2019, Calixarene-based {Co26} burr puzzle: an efficient oxygen reduction catalyst, ACS Appl. Nano Mater., 2, 4232, 10.1021/acsanm.9b00683 Waghmode, 2018, Calixarene intercalated NiCo layered double hydroxide for enhanced oxygen evolution catalysis, ACS Sustain. Chem. Eng., 6, 9649, 10.1021/acssuschemeng.7b04788 Wang, 2016, Ultrafine Pt nanoclusters confined in a calixarene-based {Ni24} coordination cage for high-efficient hydrogen evolution reaction, J. Am. Chem. Soc., 138, 16236, 10.1021/jacs.6b11218 Sharma, 2019, New class of supramolecular bowl-shaped columnar mesogens derived from thiacalix[4]arene exhibiting gelation and organic light-emitting diodes applications, ACS Omega, 4, 15862, 10.1021/acsomega.9b01776 Ma, 2021, Hydrogen bonded metal-organic supramolecule functionalized BiVO4 photoanode for enhanced water oxidation efficiency, Chem. Eng. J., 422, 10.1016/j.cej.2021.130092 Manfredi, 2021, Multibranched calix[4]arene-based sensitizers for efficient photocatalytic hydrogen production, Eur. J. Org. Chem., 2021, 284, 10.1002/ejoc.202001296 Schottle, 2019, Bulky calixarene ligands stabilize supported iridium pair-site catalysts, J. Am. Chem. Soc., 141, 4010, 10.1021/jacs.8b13013 de Silva, 2010, A bioinspired approach for controlling accessibility in calix[4]arene-bound metal cluster catalysts, Nat. Chem., 2, 1062, 10.1038/nchem.860 Okrut, 2014, Selective molecular recognition by nanoscale environments in a supported iridium cluster catalyst, Nat. Nanotechnol., 9, 459, 10.1038/nnano.2014.72 Guo, 2018, Highly efficient artificial light-harvesting systems constructed in aqueous solution based on supramolecular self-assembly, Angew. Chem. Int. Ed., 57, 3163, 10.1002/anie.201800175 Hao, 2020, A supramolecular artificial light-harvesting system with two-step sequential energy transfer for photochemical catalysis, Angew. Chem. Int. Ed., 59, 10095, 10.1002/anie.201912654 Sun, 2018, Artificial light-harvesting supramolecular polymeric nanoparticles formed by pillar[5]arene-based host-guest interaction, Chem. Commun., 54, 1117, 10.1039/C7CC09315B Sun, 2016, Stimulus-responsive light-harvesting complexes based on the pillararene-induced co-assembly of β-carotene and chlorophyll, Nat. Commun., 7, 12042, 10.1038/ncomms12042 Ogoshi, 2018, Separation of linear and branched alkanes using host-guest complexation of cyclic and branched alkane vapors by crystal state pillar[6]arene, Angew. Chem. Int. Ed., 57, 1592, 10.1002/anie.201711575 Wu, 2020, Separation of bromoalkanes isomers by nonporous adaptive crystals of leaning pillar[6]arene, Angew. Chem. Int. Ed., 59, 2251, 10.1002/anie.201911965 Jie, 2018, Near-ideal xylene selectivity in adaptive molecular pillar[n]arene crystals, J. Am. Chem. Soc., 140, 6921, 10.1021/jacs.8b02621