DataVXElectronic Materials LettersPaper
journal article·2024-03Open access

A Soluble ‘Ba(Ni-ett)’ (ett = 1,1,2,2-Ethenetetrathiolate) Derived Thermoelectric Material

Yaoyang Hu, Geoffrey Rivers, Michael P. Weir, David B. Amabilino, Christopher J. Tuck, Ricky D. Wildman, Oleg Makarovsky, Simon Woodward

Electronic Materials Letters· Volume 20· Issue 2
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Abstract

Abstract We describe the synthesis and characterisation of the first of a new class of soluble ladder oligomeric thermoelectric material based on previously unutilised ethene-1,1,2,2-tetrasulfonic acid. Reaction of Ba(OH)2 and propionic acid at a 1:1 stoichiometry leads to the formation of the previously unrecognised soluble [Ba(OH)(O2CEt)]⋅H2O. The latter when used to hydrolyse 1,3,4,6-tetrathiapentalene-2,5-dione (TPD), in the presence of NiCl2, forms a new material whose elemental composition is in accord with the formula [(EtCO2Ba)4Ni8{(O3S)2C = C(SO3)2}5]⋅22H2O (4). Compound 4 can be pressed into pellets, drop-cast as DMSO solutions or ink-jet printed (down to sub-mm resolutions). While its room temperature thermoelectric properties are modest (σmax 0.04 S cm−1 and Seebeck coefficient, αmax − 25.8 μV K−1) we introduce a versatile new oligomeric material that opens new possible synthetic routes for n-type thermoelectrics. Graphical Abstract
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OpenAlex topics: Perovskite Materials and Applications · Advanced Thermoelectric Materials and Devices · Gas Sensing Nanomaterials and Sensors

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References (37)

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1. Sun, Y., Sheng, P., Di, C., Jiao, F., Xu, W., Qiu, D., Zhu, D.: Organic thermoelectric materials and devices based on p- and n-type poly(metal 1,1,2,2-ethenetetrathiolate)s. Adv. Mater. 24, 932–937 (2012). https://doi.org/10.1002/adma.20110430510.1002/adma.201104305 ↗
2. Poleschner, H., John, W., Hoppe, F., Fanghänel, E., Roth, S.: Tetrathiafulvalene. XIX. Synthese und Eigenschaften elektronenleitender Poly-Dithiolenkomplexe mit Ethylentetrathiolat und Tetrathiafulvalentetrathiolat als Brückenliganden. J. Für Prakt. Chemie. 325, 957–975 (1983). https://doi.org/10.1002/prac.1983325061210.1002/prac.19833250612 ↗
3. Sun, Y., Xu, W., Di, C., Zhu, D.: Metal-organic complexes-towards promising organic thermoelectric materials. Synth. Met. 225, 22–30 (2017). https://doi.org/10.1016/j.synthmet.2016.12.00110.1016/j.synthmet.2016.12.001 ↗
4. E. Redel, H. Baumgart, Thermoelectric porous MOF based hybrid materials, APL Mater. 8 (2020) 060902. https://doi.org/10.1063/5.0004699.10.1063/5.0004699 ↗
5. Lu, Y., Young, D.J.: Coordination polymers for n-type thermoelectric applications. Dalt. Trans. 49, 7644–7657 (2020). https://doi.org/10.1039/D0DT00872A10.1039/D0DT00872A ↗
6. Massetti, M., Jiao, F., Ferguson, A.J., Zhao, D., Wijeratne, K., Würger, A., Blackburn, J.L., Crispin, X., Fabiano, S.: Unconventional thermoelectric materials for energy harvesting and sensing applications. Chem. Rev. 121, 12465–12547 (2021). https://doi.org/10.1021/acs.chemrev.1c0021810.1021/acs.chemrev.1c00218 ↗
7. Wan, K., Liu, Z., Schroeder, B.C., Chen, G., Santagiuliana, G., Papageorgiou, D.G., Zhang, H., Bilotti, E.: Highly stretchable and sensitive self-powered sensors based on the N-type thermoelectric effect of polyurethane/Nax(Ni-ett)n/graphene oxide composites. Compos. Commun. 28, 100952 (2021). https://doi.org/10.1016/j.coco.2021.10095210.1016/j.coco.2021.100952 ↗
8. Liu, Z., Liu, T., Savory, C.N., Jurado, J.P., Reparaz, J.S., Li, J., Pan, L., Faul, C.F.J., Parkin, I.P., Sankar, G., Matsuishi, S., Campoy-Quiles, M., Scanlon, D.O., Zwijnenburg, M.A., Fenwick, O., Schroeder, B.C.: Controlling the thermoelectric properties of organometallic coordination polymers via ligand design. Adv. Funct. Mater. 30, 2003106 (2020). https://doi.org/10.1002/adfm.20200310610.1002/adfm.202003106 ↗
9. Wolfe, R.M.W., Menon, A.K., Marder, S.R., Reynolds, J.R., Yee, S.K.: Thermoelectric performance of n-type poly(Ni-tetrathiooxalate) as a counterpart to poly(Ni-ethenetetrathiolate): NiTTO versus NiETT. Adv. Electron. Mater. Lett. 5, 1900066 (2019). https://doi.org/10.1002/aelm.20190006610.1002/aelm.201900066 ↗
10. Wolfe, R.M.W., Menon, A.K., Fletcher, T.R., Marder, S.R., Reynolds, J.R., Yee, S.K.: Simultaneous enhancement in electrical conductivity and thermopower of n-type NiETT/PVDF composite films by annealing. Adv. Funct. Mater. 28, 1803275 (2018). https://doi.org/10.1002/adfm.20180327510.1002/adfm.201803275 ↗
11. Menon, A.K., Uzunlar, E., Wolfe, R.M.W., Reynolds, J.R., Marder, S.R., Yee, S.K.: Metallo-organic n-type thermoelectrics: Emphasizing advances in nickel-ethenetetrathiolates. J. Appl. Polym. Sci. (2017). https://doi.org/10.1002/app.4440210.1002/app.44402 ↗
12. Tkachov, R., Stepien, L., Roch, A., Komber, H., Hennersdorf, F., Weigand, J.J., Bauer, I., Kiriy, A., Leyens, C.: Facile synthesis of potassium tetrathiooxalate – The “true” monomer for the preparation of electron-conductive poly(nickel-ethylenetetrathiolate). Tetrahedron 73, 2250–2254 (2017). https://doi.org/10.1016/j.tet.2017.03.01010.1016/j.tet.2017.03.010 ↗
13. Tkachov, R., Stepien, L., Grafe, R., Guskova, O., Kiriy, A., Simon, F., Reith, H., Nielsch, K., Schierning, G., Kasinathan, D., Leyens, C.: Polyethenetetrathiolate or polytetrathiooxalate? Improved synthesis, a comparative analysis of a prominent thermoelectric polymer and implications to the charge transport mechanism. Polym. Chem. 9, 4543–4555 (2018). https://doi.org/10.1039/C8PY00931G10.1039/C8PY00931G ↗
14. Sun, Y., Qiu, L., Tang, L., Geng, H., Wang, H., Zhang, F., Huang, D., Xu, W., Yue, P., Guan, Y., Jiao, F., Sun, Y., Tang, D., Di, C., Yi, Y., Zhu, D.: Flexible n-type high-performance thermoelectric thin films of poly(nickel-ethylenetetrathiolate) prepared by an electrochemical method. Adv. Mater. 28, 3351–3358 (2016). https://doi.org/10.1002/adma.20150592210.1002/adma.201505922 ↗
15. Sun, Y., Zhang, J., Liu, L., Qin, Y., Sun, Y., Xu, W., Zhu, D.: Optimization of the thermoelectric properties of poly(nickel-ethylenetetrathiolate) synthesized via potentiostatic deposition. Sci. China Chem. 59, 1323–1329 (2016). https://doi.org/10.1007/s11426-016-0175-910.1007/s11426-016-0175-9 ↗
16. Hwang, S., Potscavage, W.J., Jr., Kim, T.-W., Adachi, C.: Interplay among thermoelectric properties, atmospheric stability, and electronic structures in solution-deposited thin films of P(NaX[Niett]). Adv. Electron. Mater. Lett. 6, 1901172 (2020). https://doi.org/10.1002/aelm.20190117210.1002/aelm.201901172 ↗
17. Wu, Y., Chen, Y., Tang, M., Zhu, S., Jiang, C., Zhuo, S., Wang, C.: A highly conductive conjugated coordination polymer for fast-charge sodium-ion batteries: reconsidering its structures. Chem. Commun. 55, 10856–10859 (2019). https://doi.org/10.1039/C9CC05679C10.1039/C9CC05679C ↗
18. Jiao F., Di C., Sun Y., Sheng P., Xu W., Zhu D.: Inkjet-printed flexible organic thin-film thermoelectric devices based on p- and n-type poly(metal 1,1,2,2-ethenetetrathiolate)s/polymer composites through ball-milling. Philos. Trans. R. Soc. A Math. Phys. Eng. Sci. 372, p. 20130008 (2014). https://doi.org/10.1098/rsta.2013.000810.1098/rsta.2013.0008 ↗
19. Faulmann, C., Chahine, J., Jacob, K., Coppel, Y., Valade, L., de Caro, D.: Nickel ethylene tetrathiolate polymers as nanoparticles: a new synthesis for future applications? J. Nanoparticle Res. 15, 1–18 (2013). https://doi.org/10.1007/s11051-013-1586-510.1007/s11051-013-1586-5 ↗
20. Oshima, K., Shiraishi, Y., Toshima, N.: Novel nanodispersed polymer complex, poly(nickel 1,1,2,2-ethenetetrathiolate): preparation and hybridization for n-type of organic thermoelectric materials. Chem. Lett. 44, 1185–1187 (2015). https://doi.org/10.1246/cl.15032810.1246/cl.150328 ↗
21. Ueda, K., Yamada, Y., Terao, T., Manabe, K., Hirai, T., Asaumi, Y., Fujii, S., Kawano, S., Muraoka, M., Murata, M.: High-performance, air-stable, n-type thermoelectric films from a water-dispersed nickel-ethenetetrathiolate complex and ethylene glycol. J. Mater. Chem. A. 8, 12319–12322 (2020). https://doi.org/10.1039/D0TA04524A10.1039/D0TA04524A ↗
22. Tkachov, R., Stepien, L., Greifzu, M., Kiriy, A., Kiriy, N., Schüler, T., Schmiel, T., López, E., Brückner, F., Leyens, C.: A printable paste based on a stable n-type poly[Ni-tto] semiconducting polymer. Coatings 9, 764 (2019). https://doi.org/10.3390/coatings911076410.3390/coatings9110764 ↗
23. Menon, A.K., Meek, O., Eng, A.J., Yee, S.K.: Radial thermoelectric generator fabricated from n- and p-type conducting polymers. J. Appl. Polym. Sci. (2017). https://doi.org/10.1002/app.4406010.1002/app.44060 ↗
24. Toshima, N., Oshima, K., Anno, H., Nishinaka, T., Ichikawa, S., Iwata, A., Shiraishi, Y.: Novel hybrid organic thermoelectric materials: three-component hybrid films consisting of a nanoparticle polymer complex, carbon nanotubes, and vinyl polymer. Adv. Mater. 27, 2246–2251 (2015). https://doi.org/10.1002/adma.20140546310.1002/adma.201405463 ↗
25. Anderson, D.L.: Chemical composition of the mantle. J. Geophys. Res. Solid Earth. 88, B41–B52 (1983). https://doi.org/10.1029/JB088iS01p00B4110.1029/JB088iS01p00B41 ↗
26. Hunt, A.J., Matharu, A.S., King, A.H., Clark, J.H.: The importance of elemental sustainability and critical element recovery. Green Chem. 17, 1949–1950 (2015). https://doi.org/10.1039/C5GC90019K10.1039/C5GC90019K ↗
27. Carvillo, P., Chen, Y., Boyle, C., Barnes, P.N., Song, X.: Thermoelectric performance enhancement of calcium cobaltite through barium grain boundary segregation. Inorg. Chem. 54, 9027–9032 (2015). https://doi.org/10.1021/acs.inorgchem.5b0129610.1021/acs.inorgchem.5b01296 ↗
28. Drzewiecka-Antonik, A., Koziol, A.E., Rejmak, P., Lawniczak-Jablonska, K., Nittler, L., Lis, T.: Novel Ba(II) and Pb(II) coordination polymers based on citric acid: synthesis, crystal structure and DFT studies. Polyhedron 132, 1–11 (2017). https://doi.org/10.1016/j.poly.2017.04.02410.1016/j.poly.2017.04.024 ↗
29. Levy, L.Y., Jenard, A., Hurwitz, H.D.: Infrared investigation of ionic hydration in ion-exchange membranes. Part 1.—Alkaline salts of grafted polystyrene sulphonic acid membranes. J. Chem. Soc. Faraday Trans. 1 Phys. Chem. Condens. Phases. 76: 2558–2574 (1980). https://doi.org/10.1039/F19807602558.10.1039/F19807602558 ↗
30. Peña, L., Xu, F., Hohn, K.L., Li, J., Wang, D.: Propyl-sulfonic acid functionalized nanoparticles as catalyst for pretreatment of corn stover. J. Biomater. Nanobiotechnol. 05, 8–16 (2014). https://doi.org/10.4236/jbnb.2014.5100210.4236/jbnb.2014.51002 ↗
31. Buzzoni, R., Bordiga, S., Ricchiardi, G., Spoto, G., Zecchina, A.: Interaction of H2O, CH3OH, (CH3)2O, CH3CN, and pyridine with the superacid perfluorosulfonic membrane nafion: an IR and Raman study. J. Phys. Chem. 99, 11937–11951 (1995). https://doi.org/10.1021/j100031a02310.1021/j100031a023 ↗
32. Akiyama, F.: Evidence of conversion from carbon dioxide to unstable carbon oxides. Bull. Chem. Soc. Jpn. 63, 2131–2133 (1990). https://doi.org/10.1246/bcsj.63.213110.1246/bcsj.63.2131 ↗
33. Paes, L.W.C., Suárez, J.A., Márquez, A.M., Sanz, J.F.: First-principles study of nickel complex with 1,3-dithiole-2-thione-4,5-dithiolate ligands as model photosensitizers. Theor. Chem. Acc. 136, 1–9 (2017). https://doi.org/10.1007/s00214-017-2098-710.1007/s00214-017-2098-7 ↗
34. da Cruz, A.G.B., Wardell, J.L., Simão, R.A., Rocco, A.M.: Preparation, structure and electrochemistry of a polypyrrole hybrid film with [Pd(dmit)2]2−, bis(1,3-dithiole-2-thione-4,5-dithiolate)palladate(II). Electrochim. Acta. 52, 1899–1909 (2007). https://doi.org/10.1016/j.electacta.2006.07.06110.1016/j.electacta.2006.07.061 ↗
35. Shi, W., Wu, G., Yong, X., Deng, T., Wang, J.-S., Zheng, J.-C., Xu, J., Sullivan, M.B., Yang, S.-W.: Orbital-engineering-based screening of π-conjugated d8 transition-metal coordination polymers for high-performance n-type thermoelectric applications. ACS Appl. Mater. Interfaces. 10, 35306–35315 (2018). https://doi.org/10.1021/acsami.8b1387710.1021/acsami.8b13877 ↗
36. Madhusudan, V., Sathyanarayan, S.G., Sastry, G.S.: Electrical conductivity and stimulated thermocurrent studies in dicalcium barium propionate single crystals. Phys. Status Solidi. 66, 371–376 (1981). https://doi.org/10.1002/pssa.221066014510.1002/pssa.2210660145 ↗
37. Wing, H.J., Thompson, T.J.: The solubility of barium propionate. J. Am. Chem. Soc. 48, 104–106 (1926). https://doi.org/10.1021/ja01412a01410.1021/ja01412a014 ↗