Synthesis, structures and properties of two donor-acceptor acridone-based compounds

Area of Science:

• Organic Chemistry
• Materials Science
• Crystallography

Background:

• Acridone derivatives are valuable building blocks for functional organic materials.
• Donor-acceptor molecules are crucial for developing advanced optoelectronic devices.
• Crystallization-induced emission (CIE) is a promising phenomenon for solid-state emitters.

Purpose of the Study:

• To synthesize and characterize two new acridone-based donor-acceptor compounds: TPA-AD-DCN and CzPh-AD-DCN.
• To investigate the structural, optical, and electrochemical properties of these novel compounds.
• To explore their potential as crystallization-induced emission materials for optoelectronics.

Main Methods:

• Synthesis of TPA-AD-DCN and CzPh-AD-DCN via high-yield reactions.
• Single-crystal X-ray diffraction for structural determination.
• Hirshfeld surface analysis to understand intermolecular interactions.
• UV-Vis absorption, fluorescence spectroscopy, and cyclic voltammetry for property evaluation.
• Theoretical calculations (e.g., DFT) to complement experimental findings.

Main Results:

• Successful synthesis and structural elucidation of TPA-AD-DCN and CzPh-AD-DCN.
• Both compounds exhibit a butterfly-like molecular configuration.
• Hirshfeld surface analysis revealed significant H...H and C...H/H...C intermolecular contacts.
• Optical and electrochemical properties align with structural characteristics.
• Demonstrated potential as crystallization-induced emission materials.

Conclusions:

• The synthesized acridone-based compounds possess unique structural features and intermolecular interactions.
• Their optical and electrochemical properties are well-supported by structural data.
• TPA-AD-DCN and CzPh-AD-DCN show promise for the development of novel optoelectronic materials through CIE.