Journal
ORGANIC LETTERS
Volume 19, Issue 19, Pages 5094-5097Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02370
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Funding
- National Natural Science Foundation of China [21502049, 51573040]
- start-up funding of Hunan University [531109020043]
- Singapore MOE Tier 3 programme [MOE2014-T3-1-004]
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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 pi-pi 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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