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Fluoranthene and its π-extended diimides: Construction of new electron acceptors
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2018-09-07 , DOI: 10.1016/j.tetlet.2018.09.012
Hiroyuki Ishikawa , Koji Katayama , Jun-ichi Nishida , Chitoshi Kitamura , Takeshi Kawase

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.



中文翻译:

荧蒽及其π-延伸的二亚胺:新型电子受体的构建

首先通过马来酸酐和带有bearing烯酰亚胺单元的乙酰环酮衍生物的狄尔斯-阿尔德(DA)反应和随后的酰亚胺化反应,首先合成3,4,8,9-氟代蒽四羧酸二酰亚胺(FDI)作为稳定的黄色化合物。二(N-辛基)FDI衍生物的X射线晶体学分析揭示了平面荧蒽二酰亚胺π-系统。FDI的循环伏安图显示出很高的电子亲和力。此外,还通过by-3,4-二羧酸酰亚胺与-亚二甲苯基衍生物的DA反应制备了其包含蒽单元(DAAI)的π-延伸类似物。该化合物表现出长波长吸收和强烈的荧光中度solvatofluorochromism(Δ λ EM = 41 nm)。进行了基于密度泛函理论(DFT)的理论计算,以表征这些二酰亚胺的电子特征。

更新日期:2018-09-07
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