Dibenzo[<i>a</i>,<i>f</i>]perylene Bisimide: Effects of Introducing Two Fused Rings

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公開日
2014-08-28
資源種別
journal article
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/asia.201402688
公開者
Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>Perylene bisimides (PBIs) are fascinating dyes with various potential applications. To study the effects of introducing a dibenzo‐fused structure to the perylene moiety, π‐extended PBI derivatives with a dibenzo‐fused structure at both of the <jats:italic>a</jats:italic> and <jats:italic>f</jats:italic> bonds were synthesized. The twisted structure was characterized by X‐ray crystal structure analysis. In the cyclic voltammograms, the dibenzo[<jats:italic>a</jats:italic>,<jats:italic>f</jats:italic>]‐fused PBI showed a reversible oxidation wave at much less positive potential, relative to a dibenzo[<jats:italic>a</jats:italic>,<jats:italic>o</jats:italic>]‐fused PBI derivative. These data indicated that two ring fusions at both sides of a naphthalene moiety, which construct a tetracene core, effectively raise the HOMO level compared to fusion of one ring at each naphthalene moiety (two anthracene cores). The dibenzo[<jats:italic>a</jats:italic>,<jats:italic>f</jats:italic>]‐fused PBI derivative showed an absorption band at 735 nm with a shoulder band reaching 900 nm.</jats:p>

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