6533b7dafe1ef96bd126ed94
RESEARCH PRODUCT
Negatively Curved Nanographene with Heptagonal and [5]Helicene Units
Klaus MüllenKlaus MüllenSobi AsakoLoïc RondinJean-sébastien LauretAkimitsu NaritaAkimitsu NaritaYunbin HuZijie QiuThomas LiuCheng-wei JuCheng-wei JuDieter Schollmeyersubject
[PHYS.PHYS.PHYS-OPTICS]Physics [physics]/Physics [physics]/Optics [physics.optics]CommunicationArylResolution (electron density)General Chemistry010402 general chemistry01 natural sciencesBiochemistryCatalysis0104 chemical sciencesCrystalchemistry.chemical_compoundCrystallographyColloid and Surface ChemistrychemistryRadical ionHelicene[PHYS.QPHY]Physics [physics]/Quantum Physics [quant-ph]Arenium ionHeptagonEnantiomer[PHYS.COND]Physics [physics]/Condensed Matter [cond-mat]ComputingMilieux_MISCELLANEOUSdescription
Negatively curved nanographene (NG) 4, having two heptagons and a [5]helicene, was unexpectedly obtained by aryl rearrangement and stepwise cyclodehydrogenations. 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 supported 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–1 cm–1).
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2020-08-18 |