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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 D2 -symmetric molecule with an end-to-end twist of 97??. 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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Xiao, Y.; Mague, J. T.; Schmehl, R. H.; Haque, F. M.; Pascal Jr., R. A., Angew. Chem. Int. Ed. 2019, 58, 2831-2833Contributed by Steven BacharachReposted from Computational Organic Chemistry with permissionThe Pascal group has synthesized dodecaphenyltetracene 1.1While...
The Pascal group has synthesized dodecaphenyltetracene 1.1While this paper has little computational work, it is of interest to readers of this blog since I have discussed many aspect of aromaticity. This new tetracene is notable for its large twisting along...