Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 9, Pages 2831-2833Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201812418
Keywords
acenes; polycyclic aromatic hydrocarbons; polyphenyl aromatic compounds
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Funding
- National Science Foundation [CHE-1265507, CHE-1762452, MRI-1228232]
- Louisiana Board of Regents [LEQSF-(2002-03)-ENH-TR-67]
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Dodecaphenyltetracene (4), the largest perphenylacene yet prepared, was synthesized from known tetraphenylfuran, hexaphenylisobenzofuran, and 1,2,4,5-tetrabromo-3,6-diphenylbenzene in three steps. The X-ray structure of the deep red, highly luminescent 4 shows it to be a D-2-symmetric molecule with an end-to-end twist of 97 degrees. The central acene is encapsulated by the peripheral phenyl substituents, and as a result, the molecule is relatively unreactive and even displays reversible electrochemical oxidation and reduction.
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