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Two Colour Photoflow Chemistry for Macromolecular Design
Matthias Van De Walle1, Kevin De Bruycker1, James P Blinco1
1Centre for Materials Science, School of Chemistry and Physics, Queensland University of Technology (QUT), 2 George St., Brisbane, QLD, 4000, Australia.
Angewandte Chemie (International Ed. in English)
|May 6, 2020
Summary
This study introduces a two-color photochemical flow system for sequential reactions. It enables wavelength-selective polymer modification and ring closure, demonstrating true lambda-orthogonal photochemistry.
Area of Science:
- Photochemistry
- Polymer Chemistry
- Flow Chemistry
Background:
- Orthogonal photochemistry allows selective reactions using different light wavelengths.
- Sequential photochemical reactions in flow offer precise control and scalability.
Purpose of the Study:
- To develop and demonstrate a two-color photochemical flow system exploiting lambda-orthogonal reactions.
- To enable wavelength-selective modification of photo-caged polymer end groups.
- To achieve subsequent polymer ring closure via a [2+2] cycloaddition.
Main Methods:
- Utilized a photochemical flow setup with sequential on-line irradiation steps.
- Employed two distinct light wavelengths (350 nm and 410 nm) for selective activation.
- Incorporated both a visible-light reactive chalcone and a UV-activated photo-caged diene in the reaction mixture.
Main Results:
- Successfully demonstrated wavelength-selective end-group modification of photo-caged polymers.
- Achieved polymer ring closure through a [2+2] cycloaddition driven by photochemistry.
- Confirmed the lambda-orthogonal nature of the system, showing no interference between the two light-activated reactions.
Conclusions:
- This work pioneers the integration of lambda-orthogonal photochemistry into flow reaction systems.
- The developed system offers precise control over sequential photochemical transformations.
- Opens new avenues for complex polymer synthesis and modification using photoflow techniques.
