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Multichromophoric sugar for fluorescence photoswitching.
Stéphane Maisonneuve1, Rémi Métivier1, Pei Yu2
1PPSM, ENS Cachan, CNRS, UMR8531, 61 avenue du Président Wilson, 94235 Cachan cedex, France.
Beilstein Journal of Organic Chemistry
|July 4, 2014
Summary
This study presents a novel photoswitchable molecule that can reversibly turn its fluorescence on and off using UV and visible light. This molecular switch demonstrates excellent photo-stability for potential applications in advanced optical materials.
Area of Science:
- Supramolecular Chemistry
- Organic Electronics
- Photochemistry
Background:
- Development of photoresponsive materials is crucial for advanced applications.
- Multichromophoric systems offer complex functionalities.
- Diarylethene (DAE) photochromes and dicyanomethylenepyran (DCM) fluorophores are key components in molecular switches.
Purpose of the Study:
- To synthesize and characterize a novel multichromophoric glucopyranoside bearing DCM fluorophores and a DAE photochrome.
- To investigate the photoswitching behavior and energy transfer mechanisms within the synthesized molecule.
- To evaluate the reversibility and photo-stability of the developed molecular system.
Main Methods:
- Copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) for synthesis.
- UV-Vis spectroscopy and fluorescence spectroscopy for characterization.
- Photoirradiation experiments to induce and reverse switching.
Main Results:
- Successful synthesis of the multichromophoric glucopyranoside (compound 2).
- Demonstrated reversible photoswitching of fluorescence, controlled by UV/visible light.
- Achieved efficient Förster-type resonance energy transfer (FRET) from DCM to DAE (closed form).
- Observed excellent photo-resistance and reversibility of the switching process.
Conclusions:
- The synthesized molecule functions as an efficient and reversible molecular photoswitch.
- The system exhibits robust performance with high photo-stability.
- Potential applications in areas like optical data storage and smart materials.
