Synthesis and Properties of the Doubly Oxonium-Embedded Picenes as Electron-Deficient Polycyclic Aromatic Hydrocarbons

The doubly oxonium-embedded picenes have been synthesized for the first time. They have a rigid planar electron-deficient core and are stabilized by the pyrylium aromaticity. The doping positions of oxygen atoms influenced their electrochemical and optoelectronic properties because of the different...

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Published inOrganic letters Vol. 23; no. 10; pp. 3986 - 3990
Main Authors Matsuo, Kyohei, Toda, Natsuki, Aratani, Naoki, Yamada, Hiroko
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.05.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PYRYLIUM
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Summary:The doubly oxonium-embedded picenes have been synthesized for the first time. They have a rigid planar electron-deficient core and are stabilized by the pyrylium aromaticity. The doping positions of oxygen atoms influenced their electrochemical and optoelectronic properties because of the different charge distributions in the skeletons. The donor–acceptor–donor-type molecules baring electron-donating triphenylamine moieties exhibited intramolecular charge-transfer absorption at the visible regions, indicating the large impact of the substituents on their electronic properties.
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01188