A Photo- and Redox-Driven Two-Directional Terthiazole-Based Switch: A Combined Experimental and Computational...

Area of Science:

• Organic Chemistry
• Materials Science
• Photochemistry

Background:

• Terthiazoles are heterocyclic compounds with potential applications in molecular switches.
• Photo- and electro-chromic materials offer tunable optical and electronic properties.

Purpose of the Study:

• To synthesize and investigate the photo- and electro-chromic behavior of terthiazoles with redox-active substituents.
• To develop the first terarylene-based switch capable of both photochemical and electrochemical operation.

Main Methods:

• Synthesis of terthiazoles functionalized with N-methyl pyridinium and ferrocene groups.
• Investigation of photo- and electro-chromic properties.
• Density Functional Theory (DFT) calculations for property analysis.

Main Results:

• Terthiazoles with N-methyl pyridinium substituents showed reversible ring-closure and ring-opening reactions.
• A significant redox potential difference (700 mV) was observed between open and closed forms.
• Ferrocene incorporation inhibited photochromism but enhanced redox switchability.

Conclusions:

• Novel terthiazole-based molecular switches with dual photo- and electrochemical responsiveness were successfully developed.
• The stored chemical potential energy in the closed form has implications for energy storage applications.
• DFT calculations provided insights into the mechanisms of switching processes.