Angle-controlled synthesis and redox properties of a tetraphenylethene-based hexacationic triangular macrocycle

Area of Science:

• Organic Chemistry
• Supramolecular Chemistry
• Materials Science

Background:

• Tetraphenylethene derivatives are known for their unique photophysical properties.
• Macrocyclic compounds offer structural rigidity and defined cavities.
• Developing stimuli-responsive molecules is crucial for advanced materials.

Purpose of the Study:

• To synthesize a novel hexacationic triangular macrocycle based on tetraphenylethene.
• To investigate the redox behavior and stability of the synthesized macrocycle.
• To explore the potential for visual color changes associated with redox transformations.

Main Methods:

• Angle-controlled synthesis strategy utilizing the Zincke reaction.
• Chemical reduction using appropriate reducing agents.
• Electrochemical reduction to probe redox potentials and reversibility.

Main Results:

• Successful synthesis of the tetraphenylethene-based hexacationic triangular macrocycle (T⁶⁺·6PF₆^-).
• Demonstration of two-step reversible and stable redox transformations upon reduction.
• Observation of distinct visual color changes correlating with redox states.

Conclusions:

• The synthesized macrocycle exhibits controllable and reversible redox activity.
• The visual color change associated with redox transformations opens possibilities for sensor applications.
• This work contributes to the design of functional supramolecular systems with tunable electronic properties.