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Sterically crowded di-indazolyl-pyridines: Iron(II) complexation studies

  • Suhad Omar , Elisabeth Irran , Dennis Wiedemann , Dirk Baabe and Andreas Grohmann EMAIL logo
Published/Copyright: March 17, 2023
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 78 Issue 3-4

Abstract

4-(2,6-Di(2H-indazol-2-yl)pyridin-4-yl)benzoic acid (1) and 10-(2,6-di(1H-pyrazol-1-yl)pyridin-4-yl)anthracene-9-carboxylic acid (2) were required for adsorption studies on Ag(111), with a view to subsequent iron(II) complexation and formation of well-ordered spin-responsive self-assembled monolayers. While the generation of these compounds has remained elusive, several intermediates and by-products were obtained, potentially useful as dipyrazolylpyridine-related derivatives and for metal ion coordination. 3,5-Dichloro-2,6-diindazolylpyridine-4-amine, which forms as a mixture of regioisomers, was synthesised, the mixture separated, and the components characterised (3,5-dichloro-2,6-di(2H-indazol-2-yl)pyridin-4-amine; 3,5-dichloro-2-(1H-indazol-1-yl)-6-(2H-indazol-2-yl)pyridin-4-amine; 3,5-dichloro-2,6-di(1H-indazol-1-yl)pyridin-4-amine). Their iron(II) complexes have been prepared and fully characterised, including single crystal X-ray structure determination. The complexes are instructive examples of the influence of ligand design (“steric jamming”) on the spin-crossover (SCO) activity of FeII centres. Bulky substitution, which entails twisted ligand conformation, increases intramolecular crowding. This prevents contraction of the metal coordination sphere, which would be a prerequisite for thermally inducible SCO. Mössbauer spectroscopy has revealed that the complexes remain predominantly high-spin (HS) between 20 and 200 K, and that a mixture of conformational HS isomers is present in the microcrystalline solid.

Keywords: indazolide; iron(II); nucleophilic aromatic substitution; self-assembled monolayers; spin crossover

Dedicated to Professor Gerhard Müller on the occasion of his 70th birthday.

Corresponding author: Andreas Grohmann, Institut für Chemie, Technische Universität Berlin, Straße des 17. Juni 135, 10623 Berlin, Germany, E-mail:
Elisabeth Irran and Dennis Wiedemann, Single-crystal X-ray structure analysis. Dirk Baabe, Mössbauer spectroscopy and magnetic susceptibility measurements.

Acknowledgements

We thank Dr. G. Hörner for assistance with spin equilibrium evaluation. S. O. gratefully acknowledges a PhD scholarship from the German Academic Exchange Service (DAAD), under the programme “Forschungsstipendien – Promotionen in Deutschland”. We thank Prof. Dr. M. Bröring and Prof. Dr. F. J. Litterst (TU Braunschweig) for providing access to the SQUID magnetometer and Mössbauer spectrometer.

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: None declared.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Supplementary Material

This article contains supplementary material (https://doi.org/10.1515/znb-2023-0311).

Received: 2023-02-23
Accepted: 2023-03-01
Published Online: 2023-03-17
Published in Print: 2023-03-28

© 2023 Walter de Gruyter GmbH, Berlin/Boston

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  4. Professor Dr. Gerhard Müller. Editor-in-Chief der Zeitschrift für Naturforschung B – Chemical Sciences. zum 70. Geburtstag
  5. Research Articles
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  11. N-heterocyclic carbene-mediated oxidation of copper(I) in an imidazolium ionic liquid
  12. Synthesis, crystal structure, thermal and spectroscopic properties of ZnX2-2-methylpyrazine (X = Cl, Br, I) coordination compounds
  13. Solid-state molecular structures of Se(IV) and Te(IV) dihalides X2Se(CH3)(C6F5) and the gas-phase structure of Se(CH3)(C6F5)
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https://doi.org/10.1515/znb-2023-0311
Keywords for this article
indazolide; iron(II); nucleophilic aromatic substitution; self-assembled monolayers; spin crossover

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Preface
  4. Professor Dr. Gerhard Müller. Editor-in-Chief der Zeitschrift für Naturforschung B – Chemical Sciences. zum 70. Geburtstag
  5. Research Articles
  6. Ferrocenylmethylation of theophylline
  7. Electron density of a cyclic tetrasaccharide composed of benzoylated galactose units
  8. Orthoamide und Iminiumsalze, CIX. Umsetzungen von Orthoamiden der Alkincarbonsäuren mit Diolen, Ethandithiol und CH-aciden Nitroverbindungen
  9. 1,4-Divinylphenylene-bridged diruthenium complexes with 2-hydroxypyridine- and 2- or 8-hydroxyquinoline-olate ligands
  10. The calcium oxidotellurates Ca2(TeIVTeVIO7), Ca2(TeIVO3)Cl2 and Ca5(TeIVO3)4Cl2 obtained from salt melts
  11. N-heterocyclic carbene-mediated oxidation of copper(I) in an imidazolium ionic liquid
  12. Synthesis, crystal structure, thermal and spectroscopic properties of ZnX2-2-methylpyrazine (X = Cl, Br, I) coordination compounds
  13. Solid-state molecular structures of Se(IV) and Te(IV) dihalides X2Se(CH3)(C6F5) and the gas-phase structure of Se(CH3)(C6F5)
  14. Ein neuartiger T-förmiger 14-Elektronen-Iridium(I)-Komplex stabilisiert durch eine agostische Ir–H-Wechselwirkung
  15. Exploring dicyanamides with two different alkali-metal cations: phase separations, solid solutions and the new compound Rb1.667Cs0.333[N(CN)2]2
  16. Eu4Al13Pt9 – a coloring variant of the Ho4Ir13Ge9 type structure
  17. Decoration of the [Nb6O19]8– cluster shell with six Cu2+-centred complexes generates the [(Cu(cyclen))6Nb6O19]4+ moiety: room temperature synthesis, crystal structure and selected properties
  18. Structure and spectroscopic properties of etherates of the beryllium halides
  19. The palladium-rich silicides RE3Pd20Si6 (RE = Sc, Y and Lu)
  20. Azido and desamino analogs of the marine natural product oroidin
  21. High-pressure high-temperature preparation of CeGe3
  22. On the synthesis and crystal structure of praseodymium(III) metaborate molybdate(VI) – PrBO2MoO4
  23. A third polymorph of the zwitterionic complex trichlorido-((dimethylphosphoryl)methanaminium-κO)zinc(II)
  24. Mechanochemical synthesis and structural evaluation of a metastable polymorph of Ti3Sn
  25. Synthesis and application of calcium silicate hydrate (C-S-H) nanoparticles for early strength enhancement by eco-friendly low carbon binders
  26. Sterically crowded di-indazolyl-pyridines: Iron(II) complexation studies
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