Synthesis and thermolysis of Diels-Alder adducts of 2,9-dialkylpentacenes with diethyl azodicarboxylate

A series of Diels–Alder adducts of 2,9‐dialkylpentacenes with diethyl azodicarboxylate were synthesized, and their thermolysis behaviors or retro‐Diels–Alder reactions to regenerate dialkylpentacene were investigated via thermogravimetric analysis, IR and UV–Vis spectroscopy. Synthesized Diels–Alder...

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Bibliographic Details
Published in:Journal of physical organic chemistry 2008-03, Vol.21 (3), p.257-262
Main Authors: Okamoto, Kazuo, Shiodera, Kouta, Kawamura, Takumi, Ogino, Kenji
Format: Article
Language:English
Subjects:
2,9‐dialkylpentacene
9-dialkylpentacene
Diels-Alder adduct
molecular glass
retro-Diels-Alder reaction
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Summary:A series of Diels–Alder adducts of 2,9‐dialkylpentacenes with diethyl azodicarboxylate were synthesized, and their thermolysis behaviors or retro‐Diels–Alder reactions to regenerate dialkylpentacene were investigated via thermogravimetric analysis, IR and UV–Vis spectroscopy. Synthesized Diels–Alder adducts or precursors formed stable molecular glass. The transparent films on glass slide or silicon wafer were easily fabricated by cast or spin‐coating process. The precursors were smoothly converted to corresponding dialkylpentacenes by heating at 300°C. The domain size of regenerated dialkylpentacenes was in the range of 50–200 µm. Copyright © 2008 John Wiley & Sons, Ltd. A series of Diels‐Alder adducts of 2,9‐dialkylpentacenes with diethyl azodicarboxylate were synthesized, and their thermolysis behaviors or retro‐Diels‐Alder reactions to regenerate dialkylpentacene were investigated. The domain size of regenerated dialkylpentacenes was in the range of 50‐200 µm.
ISSN:0894-3230
1099-1395
DOI:10.1002/poc.1310