10.1002/chem.202100944
Chemistry - A European Journal
COMMUNICATION
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also attempted a similar redox interconversion of compound 10
and 11, but no reaction was confirmed.
In summary, 5,11-diazadibenzo[hi,qr]tetracene (2) was
synthesized as a new nitrogen-substituted PHA bearing a redox-
active 1,4-diazabutadiene structure. Due to the substitution of
imine-type nitrogen atoms, compound 2 showed enhanced
electron-accepting character comparable to that of conventional
n-type materials and specific reactivity toward nucleophilic
reagents. The oxidative nucleophilic substitution of hydrogen
with arylamines induced a remarkable change in the electronic
properties resulting in the aminated products 10 and 11.
Furthermore, compound 2 undergoes reversible interconversion
into its reduced form upon reduction with NaBH4, followed by
aerobic oxidation. Further investigations on potential
applications of diazadibenzo[hi,qr]tetracenes as n-type materials
or redox-active dyes are currently in progress in our laboratory.
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compound
2
is
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as
dinaphtho[1,8-bc:1',8'-
gh][1,5]naphthyridine by obeying IUPAC nomenclature and 7,14-
diazazethrene by adopting zethrene as a main skeleton.
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Acknowledgements
The authors thank Prof. Dr. Kazutaka Hirakawa at Shizuoka
University for fluorescence lifetime measurement. This work was
partly supported by JSPS KAKENHI (Grant-in-Aid for Young
Scientists, No. 19K15536) of the Ministry of Education, Culture,
Sports, Science and Technology (MEXT), Japan, and grants
from Toukai Foundation for Technology.
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Keywords: Polycyclic heteroaromatics • N-Heteroacenes • NIR-
absorption • Oxidative nucleophilic substitution of hydrogen •
Redox activity
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