Synthesis and recognition studies with a ditopic, photoswitchable deep cavitand

Area of Science:

• Supramolecular Chemistry
• Photochemistry
• Organic Synthesis

Background:

• Container molecules offer controlled environments for molecular recognition.
• Azobenzene-based spacers allow for light-induced conformational changes.
• NMR spectroscopy is crucial for characterizing molecular interactions.

Purpose of the Study:

• To synthesize novel open-ended container modules.
• To investigate the photochemical behavior of the azobiphenyl spacer.
• To characterize the binding of guest molecules within the container modules.

Main Methods:

• Organic synthesis of container modules with an azobiphenyl linker.
• Photochemical isomerization of the azobiphenyl moiety between trans and cis configurations.
• Nuclear Magnetic Resonance (NMR) spectroscopy for binding studies.

Main Results:

• Successful synthesis of container modules connected by a 4,4'-azobiphenyl spacer.
• Demonstration of access to both trans and cis azo configurations.
• Characterization of guest molecule binding using NMR methods.

Conclusions:

• The synthesized container modules exhibit tunable properties based on the azobiphenyl spacer's configuration.
• The modular design allows for controlled guest binding.
• Photochemical control over container shape and binding is achievable.