Coplanar bithiazole-centered heterocyclic aromatic fluorescent compounds having different donor/acceptor terminal...

Area of Science:

• Organic Chemistry
• Materials Science
• Photophysics

Background:

• Heterocyclic aromatic compounds are crucial in developing advanced materials.
• Bithiazole derivatives offer unique electronic and photophysical properties.
• Designing molecules with tailored D-A-A-D and A-A-A-A structures is key for functional materials.

Purpose of the Study:

• To synthesize and characterize a new family of stable and soluble bithiazole-centered fluorescent compounds.
• To investigate the structural, optical, electrochemical, and thermal properties of these novel molecules.
• To compare the properties of bithiazole-based derivatives with related bithiophene counterparts.

Main Methods:

• Synthesis of novel bithiazole-centered compounds with diverse functional tails (imidazole, pyridine, thiophene, triphenylamino, benzoic acid, ethyl benzoate).
• X-ray single-crystal structure analysis to determine molecular configurations and dihedral angles.
• Optical spectroscopy (fluorescence), electrochemical measurements (redox activity), and thermal stability testing.
• Theoretical calculations and internal reorganization energy (λ) studies.

Main Results:

• A series of stable, soluble, N-donor containing bithiazole compounds with effective π-conjugated systems were successfully synthesized.
• X-ray crystallography revealed a consistent trans coplanar configuration of the bithiazole core with varying dihedral angles to adjacent heterocycles.
• The triphenylamino-terminated compound (2TPA2TZ) exhibited yellow fluorescence, reversible redox activity, and exceptional thermal stability.
• Comparative studies highlighted differences in electronic properties and internal reorganization energy between bithiazole and bithiophene derivatives.

Conclusions:

• The synthesized bithiazole-centered compounds possess tunable electronic properties and excellent stability, suitable for advanced material applications.
• The molecular design allows for control over photophysical and electrochemical characteristics.
• These findings provide valuable insights into structure-property relationships for developing novel fluorescent materials.