Synthesis and Characterization of Polynorbornenes with Nitronaphthyl Side-Chains

Area of Science:

• Polymer Chemistry
• Organic Synthesis
• Materials Science

Background:

• Norbornene monomers are versatile building blocks for polymer synthesis.
• Naphthalene-based materials are known for their unique photophysical properties.
• Developing novel fluorescent polymers with tunable properties is an active research area.

Purpose of the Study:

• To synthesize novel norbornene monomers with naphthyl sidechains.
• To investigate the ring-opening polymerization of these monomers.
• To characterize the photophysical properties and sensing capabilities of the resulting polymers.

Main Methods:

• Synthesis and characterization of three new norbornene monomers using NMR, UV-vis, fluorescence, and mass spectrometry.
• Ring-opening polymerization using a third-generation Grubbs catalyst.
• Characterization of polymer kinetics and properties via size-exclusion chromatography and spectroscopic methods.

Main Results:

• Successful synthesis and characterization of naphthyl-based norbornene monomers.
• Established polymerization kinetics and obtained polynorbornenes with naphthalene sidechains.
• Demonstrated fluorescence in the synthesized polymers, with a notable quenching effect upon exposure to electron-rich aromatic compounds.

Conclusions:

• Novel naphthalene-based polynorbornenes were successfully synthesized and polymerized.
• The polymers exhibit inherent fluorescence and a quenching response to electron-rich analytes.
• These findings highlight the potential of these materials for developing fluorescent sensors.