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Published on: July 17, 2020
Bay- and Ortho-Octasubstituted Perylenes
Youpeng Li1, Youhua Hong1, Jing Guo1
1State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University , Changsha 410082, PR China.
A novel perylene intermediate, Per-4Br, was synthesized and used to create functional perylene dyes. These dyes exhibit tunable optoelectronic properties and maintain fluorescence in solid states due to their twisted structures.
Area of Science:
- Organic Chemistry
- Materials Science
- Supramolecular Chemistry
Background:
- Perylene derivatives are crucial in developing advanced functional materials.
- Controlling molecular structure is key to tuning optoelectronic properties.
- Steric hindrance in perylene cores can impact intermolecular interactions and solid-state luminescence.
Purpose of the Study:
- To synthesize a versatile perylene intermediate, Per-4Br.
- To explore the synthesis of novel bay- and ortho-octasubstituted perylenes.
- To investigate the structure-property relationships of these new perylene derivatives.
Main Methods:
- Regioselective oxidative radical-radical coupling for Per-4Br synthesis.
- Nucleophilic substitution and Palladium-catalyzed coupling reactions for functionalization.
- X-ray crystallographic analysis to determine molecular structure.
Main Results:
- Successful synthesis of 2,5,8,11-tetrabromo-1,6,7,12-tetrabutoxyperylene (Per-4Br).
- Generation of diverse octasubstituted perylenes with cyano, methoxy, and aryl groups.
- X-ray analysis revealed twisted molecular structures due to steric congestion.
- Absence of significant intermolecular π-π interactions observed.
- Moderate fluorescence quantum yields in the solid state were achieved.
Conclusions:
- Per-4Br is a versatile building block for functional perylene dyes.
- Molecular twisting and lack of π-π stacking influence solid-state luminescence.
- The synthesized perylene dyes offer tunable optoelectronic properties for various applications.
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