Abstract
The presence of donor groups in volatile metal compounds is interesting both in the thermochemical aspect and as the possibility to form hetero-metallic precursors by a reaction with an acceptor-capable component. Following this trend, the present work deals with synthesis and detailed structural and thermochemical investigation of a first iridium volatile complex with donor-atom-functionalized β-diketonate ligand, namely [Ir(cod)(zis)] (cod = cyclooctadiene-1,5, zis = 2-methoxy-2,6,6-trimethylheptanedionato-3,5). The compound has been characterized by elemental analysis, IR- and NMR-spectroscopy. According to single-crystal X-ray diffraction, the crystal structure of the complex is formed by layered-packed isolated molecules. Within the molecules, the coordination site IrO2C′2 (C′ is the center of C=C bond of the cod-ligand) is implemented to form distorted planar square metal coordination environment with Ir–O and Ir–C′ distances being (2.034–2.046) and (1.965–1.978) Å, respectively. TG–DTA study shows that the compound is characterized by extremely low melting point (378 K) and a high thermal stability during evaporation. Then, the temperature dependencies of saturated vapor pressures over both the solid and liquid compounds have been measured by the flow (transpiration) method at (353–376) K and (381–403) K, respectively, giving the molar enthalpy and entropy of sublimation and evaporation processes. In addition, the comparison of the structural and thermal data with the ones for the related [Ir(cod)(L)] complexes containing symmetric alkyl terminal substituents in β-diketonate ligand L has been performed and, thereby, the donor group influence on the characteristics of this type of volatile compounds has been revealed.
Similar content being viewed by others
References
Tiitta M, Niinistou L. Volatile metal β-Diketonates: ALE and CVD precursors for electroluminescent device thin films. Chem Vap Depos. 1997;3:167–82.
Igumenov IK, Basova TV, Belosludov VR. Volatile precursors for films deposition: vapor pressure, structure and thermodynamics. In: Mizutani T, editor. Application of thermodynamics to biological and materials science. Rijeka: InTech; 2011. p. 521–46.
Fahlman BD, Barron AR. Substituent effects on the volatility of metal β-diketonates. Adv Mater Opt Electr. 2000;10:223–32.
Johnson RW, Hultqvist A, Bent SF. A brief review of atomic layer deposition: from fundamentals to applications. Mater Today. 2014;17:236–46.
Mishra S, Daniele S. Metal–organic derivatives with fluorinated ligands as precursors for inorganic nanomaterials. Chem Rev. 2015;115:8379–448.
Fang G, Xu L, Cao Y, Li A. Theoretical design and computational screening of precursors for atomic layer deposition. Coord Chem Rev. 2016;322:94–103.
Krisyuk VV, Shubin YV, Senocq F, Turgambaeva AE, Duguet T, Igumenov IK, Vahlas C. Chemical vapor deposition of Pd/Cu alloy films from a new single source precursor. J Cryst Growth. 2015;414:130–4.
Krisyuk VV, Tkachev SV, Baidina IA, Korolkov IV, Turgambaeva AE, Igumenov IK. Volatile Pd–Pb and Cu–Pb heterometallic complexes: structure, properties, and trans-to-cis isomerization under cocrystallization of Pd and Cu β-diketonates with Pb hexafluoroacetylacetonate. J Coord Chem. 2015;68:1890–902.
Krisyuk VV, Baidina IA, Turgambaeva AE, Nadolinny VA, Kozlova SG, Korolkov IV, Duguet T, Vahlas C, Igumenov IK. Volatile heterobimetallic complexes from PdII and CuII β-diketonates: structure, magnetic anisotropy, and thermal properties related to the chemical vapor deposition of Cu–Pd thin films. ChemPlusChem. 2015;80:1457–64.
Krisyuk VV, Sysoev SV, Turgambaeva AE, Nazarova AA, Koretskaya TP, Igumenov IK, Morozova NB. Thermal behavior of methoxy-substituted Pd and Cu β-diketonates and their heterobimetallic complex. J Therm Anal Calorim. 2017;130:1105–10.
Krisyuk VV, Baidina IA, Kryuchkova NA, Logvinenko VA, Plyusnin PE, Korolkov IV, Zharkova GI, Turgambaeva AE, Igumenov IK. Volatile heterometallics: structural diversity of Pd–Pb β-diketonates and correlation with thermal properties. Dalton Trans. 2017;46:12245–56.
Krisyuk VV, Baidina IA, Romanenko GV, Korolkov IV, Koretskaya TP, Petrova NI, Turgambaeva AE. Structure and thermal properties of heterometallic complexes for chemical vapor deposition of Cu–Pd films. J Struct Chem. 2017;58:1522–9.
Baidina IA, Gromilov SA, Zharkova GI. Crystal and molecular structures of cis-bis-(1,1,1-trifluoro-5-methoxy-5-methyl-2,4-hexanedionato)palladium (II) and -platinum (II). J Struct Chem. 1999;40:633–9.
Vasilyev VY, Morozova NB, Basova TV, Igumenov IK, Hassan A. Chemical vapour deposition of Ir-based coatings: chemistry, processes and applications. RSC Adv. 2015;5:32034–63.
Igumenov IK, Semyannikov PP, Belaya SV, Zanina AS, Shergina SI, Sokolov IE. New volatile β-diketonate complexes of barium with sterically hindered methoxy-β-diketones as precursors for CVD. Polyhedron. 1996;15:4521–30.
Fulmer GR, Miller AJ, Sherden NH, Gottlieb HE, Nudelman A, Stoltz BM, Bercaw JE, Goldberg KI. NMR chemical shifts of trace impurities: common laboratory solvents, organics, and gases in deuterated solvents relevant to the organometallic chemist. Organometallics. 2010;29:2176–9.
Vikulova ES, Ilyin IY, Karakovskaya KI, Piryazev DA, Turgambaeva AE, Morozova NB. Volatile iridium (I) complexes with β-diketones and cyclooctadiene: syntheses, structures and thermal properties. J Coord Chem. 2016;69:2281–90.
Bespyatov MA, Kuzin TM, Naumov VN, Vikulova ES, Ilyin IY, Morozova NB, Gelfond NV. Low-temperature heat capacity of Ir(C5H7O2)(C8H12). J Chem Therm. 2016;99:70–4.
Bruker, APEX2 (Version 1.08), SAINT (Version 7.03), SADABS (Version 2.11) and SHELXTL (Version 6.12). Bruker AXS Inc., Madison, 2004
Sheldrick GM. A short history of SHELX. Acta Cryst A. 2008;64:112–22.
Vikulova ES, Cherkasov SA, Nikolaeva NS, Smolentsev AI, Sysoev SV, Morozova NB. Thermal behavior of volatile palladium(II) complexes with tetradentate Schiff bases containing propylene-diimine bridge. J Therm Anal Calorim. 2018. https://doi.org/10.1007/s10973-018-7371-z.
Zherikova KV, Zelenina LN, Pishchur DP, Emel’yanenko VN, Shoifet E, Schick C, Verevkin SP, Gelfond NV, Morozova NB. Thermochemical study of rhodium (III) acetylacetonate. J Chem Therm. 2016;102:442–50.
Volkova TV, Blokhina SV, Ryzhakov AM, Sharapova AV, Ol’khovich MV, Perlovich GL. Vapor pressure and sublimation thermodynamics of aminobenzoic acid, nicotinic acid, and related amido-derivatives. J Therm Anal Calorim. 2016;123:841–9.
Gerfin T, Hälg WJ, Atamny F, Dahmen KH. Growth of iridium films by metal organic chemical vapour deposition. Thin Solid Films. 1994;241:352–5.
Xu C, Baum TH, Rheingold AL. New precursors for chemical vapor deposition of iridium. Chem Mater. 1998;10:2329–31.
Krisyuk VV, Baidina IA, Turgambaeva AE, Korolkov IV, Koretskaya TP, Igumenov IK. Structure and thermal properties of Pb(II) complex with functionalized β-diketonate. J Organomet Chem. 2016;819:115–9.
Krasnov PO, Mikhaleva NS, Kuzubov AA, Nikolaeva NS, Zharkova GI, Sheludyakova LA, Morozova NB, Basova TV. Prediction of the relative probability and the kinetic parameters of bonds breakage in the molecules of palladium MOCVD precursors. J Mol Struct. 2017;1139:269–74.
Tucker PA. Acetylacetonato(1,5-cyclooctadiene)iridium (I). Acta Cryst B. 1981;37:1113–5.
Zharkova GI, Stabnikov PA, Sysoev SA, Igumenov IK. Volatility and crystal lattice energy of palladium(II) chelates. J Struct Chem. 2005;46:320–7.
Nandurkar NS, Bhanushali MJ, Bhor MD, Bhanage BM. Palladium bis(2,2,6,6-tetramethyl-3,5-heptanedionate): an efficient catalyst for regioselective C-2 arylation of heterocycles. Tetrahedron Lett. 2008;49:1045–8.
Utriainen M, Kröger-Laukkanen M, Johansson LS, Niinistö L. Studies of metallic thin film growth in an atomic layer epitaxy reactor using M(acac)2 (M = Ni, Cu, Pt) precursors. Appl Surf Sci. 2000;157:151–8.
Purecha VH, Nandurkar NS, Bhanage BM, Nagarkar JM. Copper bis(2,2,6,6-tetramethyl-3,5-heptanedionate) catalyzed synthesis of N-substituted ferrocenes. Tetrahedron Lett. 2008;49:1384–7.
Temple D, Reisman A. Chemical vapor deposition of copper from copper(II) hexafluoroacetylacetonate. J Electrochem Soc. 1989;136:3525–9.
Colominas C, Lau KH, Hildenbrand DL, Crouch-Baker S, Sanjurjo A. Vapor pressures of the copper and yttrium β-diketonate MOCVD precursors. J Chem Eng Data. 2001;46:446–50.
Zharkova GI, Stabnikov PA, Grankin VM, Semyannikov PP, Igumenov IK. Palladium (II) β-diketonates: volatility and energy of the crystal lattice. Russ J Coord Chem. 2000;26:576–81.
Morozova NB, Semyannikov PP, Trubin SV, Stabnikov PP, Bessonov AA, Zherikova KV, Igumenov IK. Vapor pressure of some volatile iridium(I) compounds with carbonyl, acetylacetonate and cyclopentadienyl ligands. J Therm Anal Calorim. 2009;96:261–6.
Vikulova ES, Karakovskaya KI, Ilyin IYu., Zelenina LN, Sysoev SV, Morozova NB. Thermodynamic study of volatile iridium (I) complexes with 1,5-cyclooctadiene and acetylacetonato derivatives: effect of (O,O) and (O,N) coordination sites. J Chem Therm. 2019 (In press).
Funding
The reported study was funded by RFBR and “NID” Foundation according to the research project No. 17-33-80100_mol_ev_a.
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Karakovskaya, K.I., Vikulova, E.S., Ilyin, I.Y. et al. Synthesis, structure and thermal investigation of a new volatile iridium (I) complex with cyclooctadiene and methoxy-substituted β-diketonate. J Therm Anal Calorim 137, 931–940 (2019). https://doi.org/10.1007/s10973-018-07994-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10973-018-07994-9