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Bay- and Ortho-Octasubstituted Perylenes

Author:
Li, Youpeng, Hong, Youhua, Guo, Jing, Huang, Xiaobo, Wei, Haipeng, Zhou, Jun, Qiu, Tiancheng, Wu, Jishan, Zeng, Zebing
Source:
Organic letters 2017 v.19 no.19 pp. 5094-5097
ISSN:
1523-7052
Subject:
Lewis bases, X-ray diffraction, catalytic activity, chemical reactions, dyes, electronic equipment, fluorescence, moieties, organic compounds, palladium, regioselectivity
Abstract:
A key intermediate compound, 2,5,8,11-tetrabromo-1,6,7,12-tetrabutoxyperylene (Per-4Br), was synthesized from 3,6-dibromo-2,7-dioxylnaphthalene via simple regioselective oxidative radical–radical coupling, followed by reduction and nucleophilic substitution. Various bay- and ortho-octasubstituted perylenes containing cyano, methoxy and aryl groups were then obtained by nucleophilic substitution or Pd-catalyzed coupling reactions. X-ray crystallographic analyses reveal that these new perylene molecules process a twisted structure due to steric congestion at the bay-regions and there is no obvious intermolecular π–π interaction. As a result, they exhibit moderate fluorescence quantum yields even in solid state. Therefore, Per-4Br can serve as a versatile building block for various functional perylene dyes with tunable optoelectronic property.
Agid:
5826940