Dibenzo[a,f]perylene Bisimide: Effects of Introducing Two Fused Rings |
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Authors: | Chaolumen Hiroki Enno Dr Michihisa Murata Prof?Dr Atsushi Wakamiya Prof?Dr Yasujiro Murata |
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Institution: | Institute for Chemical Research, Kyoto University, Uji, Kyoto 611‐0011 (Japan), Fax: (+81)?774‐38‐3178 |
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Abstract: | 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 a and f bonds were synthesized. The twisted structure was characterized by X‐ray crystal structure analysis. In the cyclic voltammograms, the dibenzoa,f]‐fused PBI showed a reversible oxidation wave at much less positive potential, relative to a dibenzoa,o]‐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 dibenzoa,f]‐fused PBI derivative showed an absorption band at 735 nm with a shoulder band reaching 900 nm. |
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Keywords: | benzannulation dyes perylene bisimide tetracene X‐ray analysis |
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