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Dithienylethenes with a novel photochromic performance.
Kentaro Morimitsu1, Katsunori Shibata, Seiya Kobatake
1Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, and CREST, Japan Science and Technology Corporation, Hakozaki 6-10-1, Higashi-ku, Fukuoka 812-8581, Japan.
The Journal of Organic Chemistry
|June 22, 2002
Summary
Researchers developed new dithienylethenes with excellent light stability and thermal reversibility. Bulky alkoxy groups reduced photocontrolled color fading, enhancing material durability for potential applications.
Area of Science:
- Organic Chemistry
- Materials Science
- Photochemistry
Background:
- Dithienylethenes are photochromic compounds with potential applications in optical memory and switches.
- Controlling their photochromic properties, such as decoloration quantum yields and thermal stability, is crucial for practical use.
Purpose of the Study:
- To synthesize dithienylethenes with low decoloration quantum yields and high thermal stability.
- To investigate the effect of bulky alkoxy substituents on the photochromic properties of dithienylethenes.
Main Methods:
- Synthesis of dithienylethene derivatives with bulky alkoxy substituents at the 2- and 2'-positions.
- Measurement of decoloration quantum yields under UV irradiation.
- Evaluation of thermal stability of the colored closed-ring isomers at elevated temperatures.
Main Results:
- Introduction of bulky alkoxy substituents significantly suppressed cycloreversion quantum yields to below 10(-3).
- Photogenerated color remained stable under room light conditions.
- However, bulky alkoxy substituents decreased the thermal stability of the colored closed-ring isomers, with fading observed at 160 degrees C.
Conclusions:
- Bulky alkoxy substituents are effective in enhancing the photostability of dithienylethenes by reducing decoloration quantum yields.
- There is a trade-off between photostability and thermal stability, with bulky groups reducing the latter.
- These findings provide insights for designing dithienylethene-based photochromic materials with tailored properties.