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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
Published on: December 16, 2022
Design, synthesis, and characterization of a persistent nonacene derivative
Irvinder Kaur1, Mikael Jazdzyk, Nathan N Stein
1Department of Chemistry and Materials Science Program, University of New Hampshire, Durham, New Hampshire 03824-3598, USA.
Journal of the American Chemical Society
|January 9, 2010
Summary
Researchers have synthesized the first stable nonacene derivative, overcoming oxidative degradation challenges. This breakthrough in large acene chemistry opens doors for advanced organic semiconductor materials.
Area of Science:
- Organic Chemistry
- Materials Science
- Chemical Engineering
Background:
- Large acenes are crucial for organic electronics but are difficult to synthesize due to oxidative degradation.
- Developing persistent and soluble large acenes is essential for advancing thin-film organic semiconductor applications.
Purpose of the Study:
- To overcome the technical barrier of facile oxidative degradation in the preparation of large acenes.
- To design, synthesize, isolate, and characterize the first persistent nonacene derivative.
Main Methods:
- Utilized a combination of experimental and theoretical substituent effects for molecular design.
- Employed arylthio or alkylthio substituents on the terminal rings of the nonacene skeleton.
- Characterized the resulting nonacene derivative to confirm its stability and structure.
Main Results:
- Successfully breached the technical barrier of facile oxidative degradation for large acenes.
- Synthesized and characterized the first persistent nonacene derivative.
- Demonstrated that arylthio/alkylthio substituents convert the open-shell singlet diradical to a closed-shell system, enhancing stability.
Conclusions:
- The developed molecular design strategy effectively prevents oxidative degradation of large acenes.
- The synthesized persistent nonacene derivative is a significant advancement for organic semiconductor applications.
- The substituent effects are applicable for creating other stable, soluble, large acene derivatives for advanced materials.
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