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M Savastano1, C Bazzicalupi, C García-Gallarín

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This summary is machine-generated.

This study explores how tetrazine-based ligands form complexes with halide and hydroxide anions in water. Researchers found unique solid-state structures and solution behaviors, including unprecedented hydroxide complex formation.

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Area of Science:

  • Coordination Chemistry
  • Supramolecular Chemistry
  • Anion Recognition

Background:

  • Tetrazine derivatives are versatile ligands with potential applications in anion binding.
  • Understanding anion-ligand interactions is crucial for developing new functional materials and sensors.
  • Previous studies have not extensively explored the complexation behavior of morpholine-substituted tetrazines with various anions in aqueous media.

Purpose of the Study:

  • To investigate the formation and stability of halide and hydroxide anion complexes with two specific tetrazine ligands (L1 and L2) in aqueous solution.
  • To elucidate the structural features governing these interactions in both solid and solution states.
  • To compare the complexation behavior of protonated and neutral ligands with anions.

Main Methods:

  • Potentiometric titrations and Isothermal Titration Calorimetry (ITC) were employed to study complex formation in aqueous solution.
  • Single crystal X-ray diffraction (XRD) was used to analyze the solid-state structures of halide complexes.
  • Density Functional Theory (DFT) calculations combined with the Polarizable Continuum Model (PCM) provided insights into electronic structure and solvation effects.

Main Results:

  • In the solid state, complexes exhibited 1:2 stoichiometry with halide anions (HF2-, Cl-, Br-) forming anion-π interactions with the tetrazine ring and hydrogen bonds with morpholine groups.
  • In aqueous solution, only 1:1 complexes were observed, with a stability trend of I- > F- > Br- > Cl-, rationalized by electrostatic, hydrogen bonding, anion-π, and solvent effects.
  • Unprecedented hydroxide anion ([L(OH)]-) complex formation with neutral tetrazine ligands was observed, showing comparable or higher stability than halide complexes due to favorable enthalpic contributions.

Conclusions:

  • The study reveals distinct structural motifs and stability trends for anion complexes of tetrazine ligands in solid versus solution states.
  • Anion-π interactions and hydrogen bonding play significant roles in stabilizing solid-state complexes, while solvation effects dominate in solution.
  • The formation of hydroxide complexes with neutral tetrazine ligands represents a novel finding with potential implications for anion sensing and coordination chemistry.