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Org Lett. 2017 Oct 6;19(19):5094-5097. doi: 10.1021/acs.orglett.7b02370. Epub 2017 Sep 13.

Bay- and Ortho-Octasubstituted Perylenes.

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State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University , Changsha 410082, PR China.
College of Chemistry and Materials Engineering, Wenzhou University , Wenzhou 325035, PR China.
Department of Chemistry, National University of Singapore , 3 Science Drive 3, 117543, Singapore.


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.

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