title: An Electron-Deficient Azacoronene Obtained by Radial π Extension.
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.
authors.affiliation: Wydział Chemii, Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383, Wrocław, Poland.
authors.forename: Marika
authors.initials: M
authors.lastname: Żyła-Karwowska
authors.affiliation: Wydział Chemii, Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383, Wrocław, Poland.
authors.forename: Halina
authors.initials: H
authors.lastname: Zhylitskaya
authors.affiliation: Wydział Chemii, Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383, Wrocław, Poland.|Wrocławskie Centrum Badań EIT+ ul. Stabłowicka 147, 54-066, Wrocław, Poland.
authors.forename: Joanna
authors.initials: J
authors.lastname: Cybińska
authors.affiliation: Wydział Chemii, Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383, Wrocław, Poland.
authors.forename: Tadeusz
authors.initials: T
authors.lastname: Lis
authors.affiliation: Wydział Chemii, Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383, Wrocław, Poland.
authors.forename: Piotr J
authors.initials: PJ
authors.lastname: Chmielewski
authors.affiliation: Wydział Chemii, Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383, Wrocław, Poland.
authors.forename: Marcin
authors.initials: M
authors.lastname: Stępień
keywords: aromaticity; heterocycles; polyaromatic compounds; redox chemistry; synthesis