BINOL-Containing Chiral Porous Polymers as Platforms for Enantiorecognition.

Area of Science:

• Materials Science
• Organic Chemistry
• Analytical Chemistry

Background:

• Enantioselective discrimination of racemic compounds is crucial in various scientific fields.
• Developing novel materials for chiral recognition remains an active area of research.

Purpose of the Study:

• To design and synthesize novel chiral conjugated BINOL-porous polymers (CBPPs).
• To evaluate the enantioselective recognition capabilities of CBPPs for terpenes and amines using fluorescence spectroscopy.

Main Methods:

• Synthesis of CBPPs via Suzuki-Miyaura and Sonogashira-Hagihara coupling reactions using enantiopure BINOL derivatives and various comonomers.
• Characterization of CBPPs for thermal stability, surface area, and framework robustness.
• Fluorescence titration experiments to determine enantioselectivity towards limonene, α-pinene, and 1-phenylethylamine.

Main Results:

• CBPPs exhibit high thermal stability, good specific surface area, and robust frameworks.
• Sonogashira-type CBPPs show high enantioselectivity for (R)-1-phenylethylamine and (S)-terpenes (limonene, α-pinene).
• Suzuki-type CBPPs display selectivity for (S)-1-phenylethylamine.
• Computational simulations reveal hydrogen bonding and π-π interactions as key recognition mechanisms.

Conclusions:

• The developed CBPPs are effective materials for the fluorescence-based enantioselective recognition of terpenes and amines.
• The synthetic strategy provides a versatile platform for incorporating chiral centers into porous polymers for diverse chiral applications.
• CBPPs offer enhanced selectivity compared to soluble BINOL-based systems.