Premium
Synthesis and thermolysis of Diels–Alder adducts of 2,9‐dialkylpentacenes with diethyl azodicarboxylate
Author(s) -
Okamoto Kazuo,
Shiodera Kouta,
Kawamura Takumi,
Ogino Kenji
Publication year - 2008
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1310
Subject(s) - chemistry , diethyl azodicarboxylate , adduct , thermogravimetric analysis , thermal decomposition , diels–alder reaction , decomposition , polymer chemistry , organic chemistry , catalysis , triphenylphosphine
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.