Author: Qiu, Zijie; Asako, Sobi; Hu, Yunbin; Ju, Cheng-Wei; Liu, Thomas; Rondin, Loic; Schollmeyer, Dieter; Lauret, Jean-Sébastien; Müllen, Klaus; Narita, Akimitsu
Title: Negatively Curved Nanographene with Heptagonal and [5]Helicene Units. Cord-id: gohcyus6 Document date: 2020_8_18
ID: gohcyus6
Snippet: Negatively curved nanographene (NG) 4, having two heptagons and a [5]helicene, was unexpectedly obtained by aryl rearrangement and stepwise cyclodehydrogena-tion. X-ray crystallography confirmed the saddle-shaped structures of intermediate 3 and NG 4. The favorability of rearrangement over helicene formation following radical cation or arenium cation mechanisms is sup-ported by theoretical calculations. NG 4 demonstrates a reversible mechanochromic color change and solid-state emission, presumab
Document: Negatively curved nanographene (NG) 4, having two heptagons and a [5]helicene, was unexpectedly obtained by aryl rearrangement and stepwise cyclodehydrogena-tion. X-ray crystallography confirmed the saddle-shaped structures of intermediate 3 and NG 4. The favorability of rearrangement over helicene formation following radical cation or arenium cation mechanisms is sup-ported by theoretical calculations. NG 4 demonstrates a reversible mechanochromic color change and solid-state emission, presumably benefiting from its loose crystal packing. After resolution by chiral high-performance liquid chromatography, the circular dichroism spectra of enantiomers 4-(P) and 4-(M) were measured and showed moderate Cotton effects at 350 nm (|Δε| = 148 M-1cm-1).
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