Integrated DFT and Cyclic Voltammetry Approach for Screening Redox-Active Knoevenagel Adducts with Potential...

Area of Science:

• Computational Chemistry
• Electrochemistry
• Organic Synthesis
• Materials Science

Background:

• Antioxidants are crucial for combating oxidative stress.
• Knoevenagel adducts are a class of organic compounds with potential biological activities.
• Developing efficient synthetic routes and evaluating antioxidant properties is essential.

Purpose of the Study:

• To synthesize and evaluate Knoevenagel adducts as potential antioxidant candidates.
• To investigate the relationship between molecular structure and antioxidant activity using computational methods.
• To validate theoretical predictions with experimental electrochemical data.

Main Methods:

• Synthesis of Knoevenagel adducts via microwave-assisted condensation.
• Quantum-chemical calculations (DFT) for optimizing geometries and obtaining electronic descriptors (IP, SET, MEP).
• Electrochemical analysis using cyclic voltammetry on modified electrodes.

Main Results:

• Knoevenagel adducts (1-6) were synthesized with good yields (71-85%).
• Compound 6 exhibited favorable electronic properties for antioxidant activity, with a low ionization potential (IP) and single-electron transfer (SET) value.
• Electrochemical studies confirmed compound 6's efficient electron transfer capabilities on a modified electrode.

Conclusions:

• The combined DFT and electrochemical approach effectively identifies promising antioxidant candidates.
• Knoevenagel adducts, particularly compound 6, show significant potential as antioxidants.
• This study provides a framework for designing novel redox-active compounds for antioxidant applications.