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Dibenzo[ a , f ]perylene Bisimide: Effects of Introducing Two Fused Rings
Author(s) -
Enno Hiroki,
Murata Michihisa,
Wakamiya Atsushi,
Murata Yasujiro
Publication year - 2014
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201402688
Subject(s) - moiety , perylene , tetracene , anthracene , naphthalene , ring (chemistry) , chemistry , derivative (finance) , photochemistry , crystallography , stereochemistry , molecule , organic chemistry , financial economics , economics
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 dibenzo[ a , f ]‐fused PBI showed a reversible oxidation wave at much less positive potential, relative to a dibenzo[ a , 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 dibenzo[ a , f ]‐fused PBI derivative showed an absorption band at 735 nm with a shoulder band reaching 900 nm.