An Electron‐Deficient Azacoronene Obtained by Radial π Extension |
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| Authors: | Marika Żyła‐Karwowska Dr. Halina Zhylitskaya Dr. Joanna Cybińska Prof. Tadeusz Lis Prof. Piotr J. Chmielewski Prof. Marcin Stępień |
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| Affiliation: | 1. http://www.mstepien.edu.pl;2. Wydzia? Chemii, Uniwersytet Wroc?awski, Wroc?aw, Poland;3. Wroc?awskie Centrum Badań EIT+ ul. Stab?owicka 147, Wroc?aw, Poland |
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| Abstract: | ![]()
A hexapyrrolohexaazacoronene derivative containing 37 fused rings, the largest such system to date, was obtained from a naphthalenomonoimide–pyrrole hybrid in a concise and efficient synthesis. This large heterocycle is electron‐deficient and shows extended redox activity, spanning at least 13 oxidation levels, but is otherwise chemically stable. Radial expansion of the π system creates a chromophore characterized by strong fluorescence and solvatochromism in the neutral state, and strong near‐infrared absorption in the charged states. Additionally, the enlarged and ruffled aromatic surface supports a unique self‐assembly mode in the crystal, leading to the formation of highly solvated organic clathrates. |
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| Keywords: | aromaticity heterocycles polyaromatic compounds redox chemistry synthesis |
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