Tethered together: DASA design towards aqueous compatibility

Area of Science:

• Organic chemistry
• Photochemistry
• Materials science

Background:

• Donor-acceptor Stenhouse adducts (DASAs) are known for tunable visible light absorption and negative photochromism.
• Existing DASA derivatives exhibit poor performance in polar protic solvents, hindering biological applications.
• Overcoming solvent limitations is crucial for expanding DASA utility.

Purpose of the Study:

• To develop novel DASA derivatives with improved stability and photoswitching capabilities in polar protic solvents.
• To enable the application of DASAs in biological systems and aqueous environments.
• To investigate the relationship between molecular structure and solvent compatibility.

Main Methods:

• Synthesized novel DASA derivatives with a specific substitution on the triene.
• Investigated the photoswitching behavior of these derivatives in various polar protic solvents.
• Analyzed the impact of charge separation on solvent stability and switching efficiency.

Main Results:

• The new DASA derivatives demonstrate stability and high dark equilibrium in polar protic solvents.
• Reduced charge separation in the modified DASAs allows for reversible switching in protic media.
• Successful switching was observed in THF:water mixtures, indicating broad solvent compatibility.

Conclusions:

• A novel strategy for synthesizing DASA derivatives compatible with polar protic solvents has been established.
• These findings significantly advance the potential of DASAs for applications in biological and aqueous systems.
• The developed DASAs offer a promising platform for light-controlled molecular devices in diverse environments.