Multifunctional Aliphatic Diamine-Based Polynaphthoxazines: From Synthesis and Polymerization to Bioactivity and...

Area of Science:

• Polymer Chemistry
• Materials Science
• Organic Synthesis

Background:

• Naphthoxazine systems are valuable but often require high polymerization temperatures.
• Developing novel monomers with improved processability and unique properties is crucial for advanced material applications.

Purpose of the Study:

• To synthesize and characterize novel aliphatic diamine-based naphthoxazine monomers.
• To investigate their polymerization behavior, thermal stability, photoluminescence, and biological activities.

Main Methods:

• One-pot Mannich condensation for monomer synthesis.
• FTIR and NMR spectroscopy for structural elucidation.
• Thermal analysis (TGA), photoluminescence spectroscopy, SEM, XRD, and biological assays (MIC, DPPH) for property evaluation.

Main Results:

• Successfully synthesized NZ-EDA, NZ-PDA, and NZ-HDA monomers with lower polymerization temperatures and broader processing windows.
• Poly-(NZ-PDA) demonstrated high thermal stability (T_d10 = 367 °C).
• All compounds exhibited intense blue photoluminescence and potent anticandidal activity (MIC values as low as 2 μg/mL for NZ-EDA).
• Varying antioxidant capacities were observed, with NZ-PDA showing the strongest DPPH radical scavenging.

Conclusions:

• The novel naphthoxazine monomers offer improved processability and thermal properties compared to conventional systems.
• These monomers and their polymers possess promising photoluminescent and anticandidal properties.
• The study highlights the potential of these compounds in materials science and biomedical applications, though dual antioxidant-antimicrobial efficacy was not established.