Synthesis of triazine-based materials by functionalization with alkynes

Area of Science:

• Materials Science
• Organic Chemistry
• Crystallography

Background:

• Triazine compounds are versatile building blocks in materials science.
• Understanding the structural properties of triazine derivatives is crucial for designing novel carbon-based functional networks.
• Existing research on functionalized triazines provides a foundation for exploring new synthetic routes and applications.

Purpose of the Study:

• To synthesize and characterize novel functionalized triazines, specifically tris(1-propynyl)-1,3,5-triazine and tris(1-butynyl)-1,3,5-triazine.
• To investigate the crystal structures and molecular packing of these new triazine compounds.
• To explore their potential as precursors for carbon-based materials and gain insights into molecular carbon nitride design.

Main Methods:

• Synthesis via substitution reactions of cyanuric chloride with prop-1-yne and but-1-yne.
• Crystal structure determination using X-ray diffraction.
• Characterization using NMR spectroscopy, IR spectroscopy, and differential thermal analysis/thermogravimetric analysis (DTA/TGA).
• Pyrolysis of tris(1-propynyl)-1,3,5-triazine to obtain polymeric materials.

Main Results:

• Successful synthesis of tris(1-propynyl)-1,3,5-triazine and tris(1-butynyl)-1,3,5-triazine.
• Elucidation of crystal structures, revealing planar triazine units and layer-like packing.
• Tris(1-propynyl)-1,3,5-triazine forms hydrogen-bonded zig-zag strands; tris(1-butynyl)-1,3,5-triazine exhibits parallel layered arrangements.
• Comprehensive data on structural, chemical, and thermal properties obtained through spectroscopic and thermal analyses.
• Pyrolysis yielded a new polymeric triazine-based compound with mesitylene units.

Conclusions:

• The synthesized functionalized triazines are valuable precursors for C/N/(H) compounds and building blocks for carbon-based functional networks.
• The study provides key insights into the structural properties and design principles of molecular carbon nitride materials.
• The obtained polymeric material from pyrolysis demonstrates the potential for creating advanced carbon nitride structures.