The Temperature Dependencies of the Vapor Pressure of Sn(IV) Complexes with Tridentate Iminopyridine Ligands

Authors

  • B. I. Petrov G.A. Razuvaev Institute of Organometallic Chemistry of the RAS
  • A. V. Piskunov G.A. Razuvaev Institute of Organometallic Chemistry of the RAS
  • O. Yu. Trofimova G.A. Razuvaev Institute of Organometallic Chemistry of the RAS
  • N. M. Lazarev G.A. Razuvaev Institute of Organometallic Chemistry of the RAS
  • T. S. Pochekutova G.A. Razuvaev Institute of Organometallic Chemistry of the RAS
  • V. V. Semenov G.A. Razuvaev Institute of Organometallic Chemistry of the RAS

Keywords:

organometallic tin(IV) complexes, Schiff bases, DSC, Knudsen effusion method, phase transition, vapor pressure, thermodynamic parameters of sublimation

Abstract

Studying the thermal properties and obtaining the temperature dependences of the saturated vapor pressure of Sn (IV) complexes with tridentate iminopyridine ligands by differential scanning calorimetry and the Knudsen effusion method allows the studied compounds to be used to obtain films and coatings acting as luminescent materials, as well as components for nonlinear optics. The following coordination compounds of tin(IV) containing tridentate Schiff bases were selected as objects of research: 4-(tert-butyl)-2-((pyridin-2-ylmethylene)amino)phenolatotrichlorotin(IV) (1), 2,4-di-tert-butyl-6-((pyridin-2-ylmethylene)amino)phenolatotrichlorotin(IV) (2), 4-methyl-2-((pyridin-2-ylmethylene)amino)phenolatotrichlorotin(IV) (3), 5-methyl-2-((pyridin-2-ylmethylene)amino)pheno­latotrichlorotin(IV) (4), and 4-chloro-2-((pyridin-2-ylmethylene)amino)phenolatotrichlorotin(IV) (5). These compounds were prepared by template synthesis from tin tetrachloride, various o-aminophenols and α-carbonyl substituted pyridines containing the iminopyridine functional group capable of covalently binding a phenolic group to a metal. The composition and structure of the complexes have been confirmed by elemental analysis, IR and NIR spectroscopy. The X-ray diffraction data, obtained at 120 K on an Agilent Xcalibur diffractometer (ω scanning, MoKα radiation, λ = 0.71073 Å) for crystals 220H25N2OCl3Sn, M = 534.502; monoclinic syngony, symmetry group P21/с; cell parameters: a = 13.9657(2), b = 12.12140(10),
c = 14.3489(2) Å; β = 109.512(2) degrees; V = 2289.68 Å3; total reflections 45565; independent reflections 6696; Rint 0.0525; R1 = 0.0262, wR2 = 0.0469]. The tin coordination polyhedron is a distorted octahedron, with heteroatoms of an organic ligand and one of the halide substituents in the equatorial plane. The remaining two chlorine ligands occupy an apical position. The tridentate ligand is almost flat. The structure is registered with the Cambridge Structural Data Bank (No. 1849152; ccdc.cam.ac.uk/getstructures). The phase transitions of compounds 1–5 have been studied in the temperature range 25–500 °C using the DSC method. For all the studied complexes an endothermic transition associated with melting has been revealed. The temperature dependences of the saturated vapor pressure of complexes 1–5 have been obtained using the Knudsen effusion method with weight recording of the sublimated substance amount in the temperature ranges 221–256, 240–270, 229–259, 220–260, and 204–240 °C for 1, 2, 3, 4, and 5, respectively. The thermodynamic parameters of sublimation processes have been calculated. The effect of the structure and substituents in the ligand on the volatility of the studied compounds has been established.

Author Biographies

B. I. Petrov, G.A. Razuvaev Institute of Organometallic Chemistry of the RAS

доктор технических наук, ведущий научный сотрудник, заместитель директора

A. V. Piskunov, G.A. Razuvaev Institute of Organometallic Chemistry of the RAS

доктор химических наук, профессор РАН, заместитель директора

O. Yu. Trofimova, G.A. Razuvaev Institute of Organometallic Chemistry of the RAS

кандидат химических наук, научный сотрудник

N. M. Lazarev, G.A. Razuvaev Institute of Organometallic Chemistry of the RAS

кандидат химических наук, научный сотрудник

T. S. Pochekutova, G.A. Razuvaev Institute of Organometallic Chemistry of the RAS

научный сотрудник

V. V. Semenov, G.A. Razuvaev Institute of Organometallic Chemistry of the RAS

доктор химических наук, ведущий научный сотрудник

References

Темплатный синтез комплексов олова(IV) с тридентатными иминоприридиновыми лигандами / А.В. Пискунов, О.Ю. Трофимова, А.В. Малеева и др. // Координационная химия. – 2019. – Т. 45, № 3. – С. 158–169. DOI: 10.1134/S0132344X1902004X

Kumar, S. New Diorganotin(IV) Complexes of Salicylaldehyde Based Hydrazones Bearing Furan Heterocycle Moiety: X-ray Structural Investigation of Dimethyltin(IV) and Diphenyltin(IV) Complexes / S. Kumar, M. Nath // J. Organomet. Chem. – 2018. – V. 856. – P. 87–99. DOI: 10.1016/j.jorganchem.2017.12.037

Synthesis, Characterization, Crystal Structure and Supramolecular Features of Bicycloazastannoxides Derived from Schiff Bases with L-Tyrosine / T.S.B. Baula, P. Kehie, A.Duthie et. al. // J. Organomet. Chem. – 2017. – V. 828. – P. 96–105. DOI: 10.1016/j.jorganchem.2016.11.028

Dinuclear Heptacoordinate Dibutyltin(IV) Complexes Derived from Schiff Bases and Dicarboxylates: Dynthesis, Cytotoxicity and Antioxidant Activity / A. Ramirez-Jimenez, R. Luna-Garcia, A. Cotes-Lozada et. al. // J. Organomet. Chem. – 2013. – V. 738. – P. 10–19. DOI: 10.1016/j.jorganchem.2013.03.038

Synthesis and Characterization of Tin(IV) and Organotin(IV) Complexes of [N’-2-Hydroxyyphenyl-6-Methylpyridine-2-Carbaldimine. X-ray Crystal Structures of n-Butyldichloro[N’-2-Hydroxyyphenyl-6-Methylpyridine-2-Carbaldiminato(1-)N,N’,O]Tin(IV) and n-diphenylchloro[N’-2-Hydroxyyphenyl-6-Methylpyridine-2-Carbaldiminato(1-)N,N’,O]Tin(IV) / S.B. Teo, H.-S. Teo,

S-T. Chang et. al. // J. Coord. Chem. – 2000. – V. 49, № 4. – P. 269–280. DOI: 10.1080/00958970008022237

Ramirez-Jimenez, A. Penta- and Heptacoordinated Tin(IV) Compounds Derived from Pyridine Schiff Bases and 2-Pyridine Carboxylate: Synthesis and Structural Characterization / A. Ramirez-Jimenez, E. Gomez, S. Hernandez // J. Organomet. Chem. – 2009. – V. 694, № 18. – P. 2965–2975. DOI: 10.1016/j.jorganchem.2009.04.035

Synthesis, Characterization and Antimicrobial Activity of Triorganotin(IV) Derivatives of Some Bioactive Schiff Base Ligands / P. Bhatra, J. Sharma, R.A. Sharma et. al. // Appl. Organomet. Chem. – 2016. – V. 31, № 7. – P. 3639. DOI: 10.1002/aoc.3639

Bis-Dorganotin(IV) Complexes with Binucleating Hydrozones Derived from a Methylene-Bis-Aromatic Aldehyde as Linker: Synthesis, Spectral and Structural Characterization, Antibacterial Activity and DNA Cleavage Studies / H. Zafarian, T. Sedaghat, H. Motamedi et. al. // J. Organomet. Chem. – 2009. – V. 853. – P. 184–192. DOI: 10.1016/j.jorganchem.2017.10.040

Ahlawat, A. Synthesis, Characterization, Antimicrobial Evaluation and QSAR Studies of Organotin(IV) Complexes of Schiff Base Ligands of 2-Amino-6-Substituted Benzothiazole Derivatives / A. Ahlawat, V. Singh, S. Asija // Chem. Papers. – 2017. – V. 71, № 11. – P. 2195–2208. DOI: 10.1007/s11696-017-0213-9

Kovala-Demertzi, D. Recent Advances on Non-Steroidal Anti-Inflammatory Drugs, NSAIDs: Organotin Complexes of NSAIDs / D. Kovala-Demertzi // J. Organomet. Chem. – 2006. – V. 691, № 8. – P. 1767–1774. DOI: 10.1016/j.jorganchem.2005.11.058

Synthesis, Structure and Property of Diorganotin Complexes with Chiral

N-(5 Chlorosalicylidene)Valinate Ligand / L. Tian, Y. Yao, Y. Wang et. al. // J. Mol. Stuct. – 2018. – V. 1156. – P. 441–449. DOI: 10.1016/j.molstruc.2017.11.132

Two-Proton Absorption Properties of Four New Pentacoordinated Diorganjtin Complexes Derived from Schiff Bases with Fluorine / A. Enriquez-Cabrera, A. Vega-Penaloza, V. Alvarez-Venicio et al. // Organomet. Chem. – 2018. – V. 855. – P. 51–58. DOI: 10.1016/j.jorganchem.2017.12.014

Effect of the π-Conjugation Length of Bipyridil Ligand on the Photophysical Properties of Binuclear Organotin(IV) Complexes: Synthesis and Characterization of Dimethyltin(IV) Complexes with Bipyridyl / E. Najafi, M.M. Amini, M. Janghouri et al. // Inorg. Chim. Acta. – 2014. – V. 415. – P. 52–60. DOI: 10.1016/j.ica.2014.02.032

Relationship Between Electroluminescence and Current Transport in Organic Heterojunction Light-Emitting Devices / P.E. Borrows, S.V. Bulovic, D.M. McCarty et al. // J. Appl. Phys. – 1996. – V. 79, № 10. – Р. 7991–8005. DOI: 10.1063/1.111453

Tetravalent Tin Complex with Electron Affinity for Electroluminescent Application / X.T. Tao, M. Shimomura, H. Suzuki et. al. // Appl. Phys. Lett. – 2000. – V. 76, № 24. – P. 3522–3524. DOI: 10.1063/1.126694

Microwave-Assisted Synthesis, Third-Order Nonlinear Optical Propreties, Voltammetry Cyclic and Theoretical Calculations of Organotin Compounds Bearing Push-Pull Schiff bases / M.C. Garcia-Lopez, B.M. Munoz-Florez, R. Chan-Navarro et al. // Organomet. Chem. – 2018. – V. 806. – P. 68–76. DOI: 10.1016/j.jorganchem.2016.01.030

SAINT. Madison (WI, USA): Bruker AXSInc., 2012.

Krause, L. Comparison of Silver and Molybdenum Microfocus X-ray Sourced for Single-Crystal Structure Determination / L. Krause, R. Herbst-Irmer, G.M. Sheldrick et al. // J. Appl. Cryst. – 2015. – V. 48, № 1. – P. 3–10. DOI: 10.1107/S1600576714022985.

Sheldrick, G.M. Crystal Structure Refinement with SHELXL / G.M. Sheldrick // Acta Crystallogr. C – 2015. – V. 71, № 1. – P. 3–8. DOI: 10.1107/S2053229614024218.

Agilent. CrysAlis PRO. Yarnton (Oxfordshiore, England): Agilent Technologies Ltd, 2014.

Hohne, G.W.H. Differential Scanning Calorimetry / G.W.H. Hohne, W.F. Hemminger, H.F. Flammersheim, Berlin; Heidelberg: Springer-Verlag, 2003. – 299 p.

Drebushchak, V.A. Calibration Coefficient of a Heat-Flow DSC. Part II. Optimal Calibration Procedure / V.A. Drebushchak // J. of Therm. and Cal. – 2005. – V. 79, № 1. – P. 213–218.

DOI: 10.1007/s10973-004-0586-1

Knudsen, M. Die Molekularstromung der Gase durch Offnungen und die Effusion / M. Knudsen. – 1909. – V. 333, № 5. – P. 999–1016. DOI: 10.1002/andp.19093330505

Лебедев, Ю.А. Термохимия парообразования органических веществ / Ю.А. Лебедев, Е.А. Мирошниченко. – М.: Наука, 1981. – 216 с.

Сыркин, В.Г. Карбонилы металлов / В.Г. Сыркин. – М.: Наука, 1983. – 200 с.

Published

2020-08-16