1. Fluoranthene and its π-extended diimides: Construction of new electron acceptors
- Author
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Hiroyuki Ishikawa, Jun-ichi Nishida, Koji Katayama, Takeshi Kawase, and Chitoshi Kitamura
- Subjects
chemistry.chemical_classification ,Anthracene ,010405 organic chemistry ,Organic Chemistry ,Maleic anhydride ,Electron acceptor ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Acenaphthylene ,0104 chemical sciences ,chemistry.chemical_compound ,Crystallography ,chemistry ,Diimide ,Drug Discovery ,Density functional theory ,Imide ,Derivative (chemistry) - Abstract
3,4,8,9-Fluoranthenetetracarboxylic diimides (FDI) are first synthesized as stable yellow compounds by the Diels-Alder (DA) reaction of maleic anhydride and acecyclone derivative bearing an acenaphthylene imide unit and subsequent imidations. An X-ray crystallographic analysis of di(N-octyl)FDI derivative reveals the planar fluoranthene diimide π -system. The cyclic voltammograms of FDIs shows considerably high electron affinity. Moreover, its π -extended analogue involving an anthracene unit (DAAI) was also prepared by the DA reaction of acenaphthylene-3,4-dicarboxylic imide with o-xylylene derivative. The compound exhibits long wavelength absorption and intense fluorescence with moderate solvatofluorochromism (ΔλEM = 41 nm). Theoretical calculations based on density function theory (DFT) were performed to characterize the electronic feature of these diimides.
- Published
- 2018
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