Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 43, Pages 13470-13474Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201707397
Keywords
conjugation; organic semiconductors; sensors; solid-state emission; trichalcogenasumanenes
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Funding
- National Key RAMP
- D Program of China [2017YFA0204903]
- National Natural Science Foundation of China [21522203, 51733044, 51525303]
- Fundamental Research Funds for the Central Universities [lzujbky-2016-ct06]
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The regioselective transformation of heterobuckybowl trichalcogenasumanenes 1 a,b at peripheral butoxy groups afforded trichalcogenasumanene ortho-quinones 2 a,b. Compounds 2 a,b are distinct from 1 a,b in terms of their molecular geometry and electronic state; that is, they have a shallower bowl depth and show absorbance in the NIR region. The reaction of 2 a,b with diamines resulted in a variety of heteropolycycles, including molecular spoon 3 a-6a, planar pi-systems 3 b-6b, and highly twisted [7-6-6]-fused systems 7 a,b. These new heteropolycycles had different optical/electrical properties: 4 a,b showed hole mobility of approximately 0.002cm(2)V(-1)s(-1), 6a displayed red emission in both solution and the solid state, and 7 a,b formed tight stacks of the curved pi-surface.
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