pi-Extended Diaza[7]helicenes by Hybridization of Naphthalene Diimides and Hexa-peri-hexabenzocoronenes
Dusold C, Sharapa DI, Hampel F, Hirsch A (2021)
Publication Type: Journal article
Publication year: 2021
Journal
Abstract
The synthesis of an unprecedented, pi-extended hexabenzocorene (HBC)-based diaza[7]helicene is presented. The target compound was synthesized by an ortho-fusion of two naphthalene diimide (NDI) units to a HBC-skeleton. A combination of Diels-Alder and Scholl-type oxidation reactions involving a symmetric di-NDI-tolane precursor were crucial for the very selective formation of the helical superstructure via a hexaphenyl-benzene (HPB) derivative. The formation of the diaza[7]helicene moiety in the final Scholl oxidation is favoured, affording the symmetric pi-extended helicene as the major product as a pair of enantiomers. The separation of the enantiomers was successfully accomplished by HPLC involving a chiral stationary phase. The absolute configuration of the enantiomers was assigned by comparison of circular dichroism spectra with quantum mechanical calculations.
Authors with CRIS profile
Carolin Dusold
Lehrstuhl für Organische Chemie II
Frank Hampel
Lehrstuhl für Organische Chemie I
Andreas Hirsch
Lehrstuhl für Organische Chemie II
Involved external institutions
Germany (DE)How to cite
APA:
Dusold, C., Sharapa, D.I., Hampel, F., & Hirsch, A. (2021). pi-Extended Diaza[7]helicenes by Hybridization of Naphthalene Diimides and Hexa-peri-hexabenzocoronenes. Chemistry - A European Journal. https://dx.doi.org/10.1002/chem.202003402
MLA:
Dusold, Carolin, et al. "pi-Extended Diaza[7]helicenes by Hybridization of Naphthalene Diimides and Hexa-peri-hexabenzocoronenes." Chemistry - A European Journal (2021).
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