Abstract
Functional groups adjacent to the redox active center would have an uncompromising effect on the diffusion kinetics of the charge carriers. They expedite the diffusion process by extensive H-bonding, charge delocalization, and functional group polarization by tautomerism or resonance which would have long held influence on the electrochemical performance of the material. Herein, we introduced a ketonic functional group adjacent to the quinoxaline redox center which accelerates the diffusion of the charge carriers. Quinoxaline nuclei with free rotating phenyl rings (DAB) exhibited a specific capacitance of 156.4 mAhg−1 at 50 mAg−1 which was found drastically decreased due to the excessive dissolution of the material as well as the uncontrolled ring flipping of the phenyl rings. By introducing a ketone functional group and stagnant phenyl rings with a fused ring system the specific capacitance was found to be improved to a considerable extent. The quinoxaline redox center with a fused ring system and symmetrically placed ketone functional groups (TKQ) exhibited a specific capacitance of 286.7 mAhg−1 at 50 mAg−1 and remained 224.8 mAhg−1 after prolonged 1000 cycles, with 95% coulombic efficiency and 79.4% retention in the discharge capacity. The study suggests that smart molecular engineering is necessary for excellent rate performance, rate reversibility, coulombic efficiency, and capacity retention.
Graphical abstract
Similar content being viewed by others
References
Poizot P, Gaubicher J, Renault S, Dubois L, Liang Y, Yao Y (2020) Chem Rev 120:6490–6557
Schon TB, McAllister BT, Li P-F, Seferos DS (2016) Chem Soc Rev 45:6345–6404
Friebe C, Lex-Balducci A, Schubert US (2019) Chemsuschem 12:4093–4115
Liang Y, Yao Y (2018) Joule 2:1690–1706
Bhosale ME, Chae S, Kim JM, Choi JY (2018) J Mater Chem A 6:19885–19911
Novák P, Müller K, Santhanam KSV, Haas O (1997) Chem Rev 97:207–282
Wang Q, Xu X, Yang G, Liu Y, Yao X (2020) Chem Commun 56:11859–11862
Nishide H, Suga T, Battery OR (2005) Electrochem. Soc Interface 14:32–36
Nguyen TP, Easley AD, Kang N, Khan S, Lim SM, Rezenom YH, Wang S, Tran DK, Fan J, Letteri RA, He X et al (2021) Nature 593:61–66
Tu XC, Wu Z, Geng X, Qu L-L, Sun H-M, Lai C, Li D-S, Zhang S (2021) J Mater Chem A 9:18306–18312
Chola NM, Nagarale RK (2022) New J Chem 46:22593–22601
Patil N, Mavrandonakis A, Jérôme C, Detrembleur C, Casado N, Mecerreyes D, Palma J, Marcilla R (2021) J Mater Chem A 9:505–514
Wang Y, Yang Z, Xia T, Pan G, Zhang L, Chen H, Zhang J (2019) ChemElectroChem 6:5080–5085
Man Z, Li P, Zhou D, Zang R, Wang S, Li P, Liu S, Li X, Wu Y, Liang X, Wang G (2019) J Mater Chem A 7:2368–2375
Chen Z, Sun P, Bai P, Su H, Yang J, Liu Y, Xu Y, Geng Y (2021) Chem Commun 57:10791–10794
Han C, Li H, Shi R, Zhang T, Tong J, Li J, Li B (2019) J Mater Chem A 7:23378–23415
Zhang S, Li Z, Cai L, Li Y, Pol VG (2021) Chem Eng J 416:129171
Chola NM, Nagarale RK (2022) J Electrochem Soc Meet Abstr MA 2022–02:21
Nikumbe DY, Sreenath S, Paramasivam S, Pawar CM, Bavdane PP, Kumar SS, Nagarale RK (2021) J Energy Storage 40:102689
Zhang J, Yang Z, Shkrob IA, Assary RS, Tung SO, Silcox B, Duan W, Zhang J, Su CC, Hu B, Pan B et al (2017) Adv Energy Mater 7:1701272
Huang J, Su L, Kowalski JA, Barton JL, Ferrandon M, Burrell AK, Brushett FR, Zhang L (2015) J Mater Chem A 14971–14976
Tabor DP, Gómez-Bombarelli R, Tong L, Gordon RG, Aziz MJ, Aspuru-Guzik A (2019) J Mater Chem A 7:12833–12841
Kim H, Goodson III T, Zimmerman PM (2016) J Phys Chem C 120:22235–22247
Wang S, Wang L, Zhu Z, Hu Z, Zhao Q, Chen J (2014) Angew Chem Int Ed 53:5892–5896
Delaporte N, Trudeau ML, Bélanger D, Zaghib K (2020) Materials 13:942
Assary RS, Zhang L, Huang J, Curtiss LA (2016) J Phys Chem C 120:14531–14538
Marenich AV, Ho J, Coote ML, Cramer CJ, Truhlar DG (2014) Phys Chem Chem Phys 16:15068–15106
Mao Y, Head-Gordon M, Shao Y (2018) Chem Sci 9:8598–8607
Conradie J (2015) J Phys: Conf Ser 633:012045
Xie J, Rui X, Gu P, Wu J, Xu ZJ, Yan Q, Zhang Q (2016) ACS Appl Mater Interfaces 8:16932–16938
Wang B, Zhang Y, Zhu Y, Shen Y-M, Wang W, Chen Z, Cao J, Xu J (2020) J Power Sources 451:227788
Wang Q, Liu Y, Chen P (2020) J Power Sources 468:228401
Chao D, Liang P, Chen Z, Bai L, Shen H, Liu X, Xia X, Zhao Y, Savilov SV, Lin J, Shen ZX (2016) ACS Nano 10:10211–10219
Lin Z, Shi H-Y, Lin L, Yang X, Wu W, Sun X (2021) Nat Commun 12:4424
Chola NM, Sreenath S, Dave B, Nagarale RK (2019) Electrophoresis 40:2979–2987
Schied T, Nickol A, Heubner C, Schneider M, Michaelis A, Bobeth M, Cuniberti G (2021) ChemPhysChem 22:885–893
He P, Quan Y, Xu X, Yan M, Yang W, An Q, He L, Mai L (2017) Small 13:1702551
Renz D, Cronau M, Roling B (2021) J Phys Chem C 125:2230–2239
Cabañero MA, Boaretto N, Röder M, Müller J, Kallo J, Latz A (2018) J Electrochem Soc 165:A847–A855
Lee YS, Ryu K-S (2017) Sci Rep 7:16617
Tang B, Zhao J, Xu J-F, Zhang X (2020) Chem Sci 11:1192–1204
Kim B, Storch G, Banerjee G, Mercado BQ, Castillo-Lora J, Brudvig GW, Mayer JM, Miller SJ (2017) J Am Chem Soc 139:15239–15244
Chola NM, Nagarale RK (2022) J Electrochem Soc 169:040534
Leung P, Aili D, Xu Q, Rodchanarowan A, Shah AA (2018) Sustainable Energy Fuels 2:2252–2259
Gorbachev V, Tsybizova A, Miloglyadova L, Chen P (2022) J Am Chem Soc 144:9007–9022
Dereka B, Lewis NHC, Zhang Y, Hahn NT, Keim JH, Snyder SA, Maginn EJ, Tokmakoff A (2022) J Am Chem Soc 144:8591–8604
Haldar S, Wang M, Bhauriyal P, Hazra A, Khan AH, Bon V, Isaacs MA, De A, Shupletsov L, Boenke T, Grothe J, Brunner HT, E., Feng X. Dong, R., Schneemann A., Kaskel S., (2022) J Am Chem Soc 144:9101–9112
Sebti E, Evans HA, Chen H, Richardson PM, White KM, Giovine R, Koirala KP, Xu Y, Gonzalez-Correa E, Wang C, Brown CM, Cheetham AK, Canepa P, Clément RJ (2022) J Am Chem Soc 144:5795–5811
Tuttle MR, Davis ST, Zhang S (2021) ACS Energy Lett 6:643–649
Tang M, Zhu S, Liu Z, Jiang C, Wu Y, Li H, Wang B, Wang E, Ma J, Wang C (2018) Chem 4:2600–2614
Qiao L, Rodriguez Pena S, Martínez-Ibañez M, Santiago A, Aldalur I, Lobato E, Sanchez-Diez E, Zhang Y, Manzano H, Zhu H, Forsyth M et al (2022) J Am Chem Soc jacs.2c02260
Chao D, Liang P, Chen Z, Bai L, Shen H, Liu X, Xia X, Zhao Y, Savilov SV, Lin J, Shen ZX (2016) ACS Nano 10:10211–10219
Chen C, Li Z, Xu Y, An Y, Wu L, Sun Y, Liao H, Zheng K, Zhang X (2021) ACS Sustainable Chem Eng 9:13268–13276
Muench S, Wild A, Friebe C, Häupler B, Janoschka T, Schubert US (2016) Chem Rev 116:9438–9484
Chola NM, Nagarale RK (2020) J Electrochem Soc 167:100552
Chola NM, Nagarale RK (2022) Mater Adv 3:4310–4321
Chola NM, Singh V, Verma V, Nagarale RK (2022) J Electrochem Soc 169:020503
Chola NM, Nagarale RK (2021) J Electrochem Soc 168:100501
Kundu D, Oberholzer P, Glaros C, Bouzid A, Tervoort E, Pasquarello A, Niederberger M (2018) Chem Mater 30:3874–3881
Glatz H, Lizundia E, Pacifico F, Kundu D (2019) ACS Appl Energy Mater 2:1288–1294
Häupler B, Rössel C, Schwenke AM, Winsberg J, Schmidt D, Wild A, Schubert US (2016) NPG Asia Mater 8:e283–e283
Dibden JW, Meddings N, Owen JR, Garcia-Araez N (2018) ChemElectroChem 5:445–454
Kim J, Park S, Hwang S, Yoon WS (2022) J Electrochem Sci Technol 13:19–31
Das PR, Komsiyska L, Osters O, Wittstock G (2015) J Electrochem Soc 162:A674–A678
Liu Y, Xie L, Zhang W, Dai Z, Wei W, Luo S, Chen X, Chen W, Rao F, Wang L, Huang Y (2019) ACS Appl Mater Interfaces 11:30943–30952
Shi H-Y, Ye Y-J, Liu K, Song Y, Sun X (2018) Angew Chem Int Ed 57:16359–16363
Li H, Sun M, Zhang T, Fang Y, Wang G (2014) J Mater Chem A 2:18345–18352
Ko SH, Kim SW, Lee YJ (2021) Sci Rep 11:21101
Bizeray AM, Howey DA, Monroe CW (2016) J Electrochem Soc 163:E223–E229
Qiu P, Agne MT, Liu Y, Zhu Y, Chen H, Mao T, Yang J, Zhang W, Haile SM, Zeier WG, Janek J, Uher C, Shi X, Chen L, Snyder GJ (2018) Nat Commun 9:2910
Zhang Y, Du N, Yang D (2019) Nanoscale 11:19086–19104
Wang A, Kadam S, Li H, Shi S, Qi Y (2018) npj Comput Mater 4:15
Desai P, Huang J, Hijazi H, Zhang L, Mariyappan S, Tarascon JM (2021) Adv Energy Mater 11:2101490
Luo H, Papaioannou N, Salvadori E, Roessler MM, Ploenes G, van Eck ER, Tanase LC, Feng J, Sun Y, Yang Y, Danaie M et al (2019) ChemSusChem 12:4432–4441
Jensen AC, Olsson E, Au H, Alptekin H, Yang Z, Cottrell S, Yokoyama K, Cai Q, Titirici MM, Drew AJ (2020) J Mater Chem A 8:743–749
Ren W, Cheng J, Ou H, Huang C, Titirici M, Wang X (2019) mChemSusChem 12:3257–3262
Acknowledgements
The director, CSIR-CSMCRI, is acknowledged for his gracious support and inspiration. The divisional chair of MSST department and the Analytical & Instrumentation Facility of CSMCRI-CSIR Bhavnagar are also greatly acknowledged.
Funding
RKN thanks for the financial support grant no. DST/TMD/MES/2K18/194(G) from Technology Mission Division, Energy and Water, and CSIR project number MLP-0320. CSMCRI-CSIR manuscript number 116/2022.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare no competing interests.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
10008_2023_5689_MOESM1_ESM.docx
Supplementary file1 The supporting information contains physical and spectral studies of the compounds (NMR, Mass spectra, cyclic voltammograms), figures, and the reference comparison table. (DOCX 15678 KB)
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Chola, N.M., Nagarale, R.K. Quinoxaline derivatives as cathode for aqueous zinc battery. J Solid State Electrochem 28, 419–431 (2024). https://doi.org/10.1007/s10008-023-05689-2
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10008-023-05689-2