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π‐Extended Diaza[7]helicenes by Hybridization of Naphthalene Diimides and Hexa‐peri‐hexabenzocoronenes

Dusold, Carolin; Sharapa, Dmitry I.; Hampel, Frank; Hirsch, Andreas

Abstract:
The synthesis of an unprecedented, π‐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 π‐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.

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Verlagsausgabe §
DOI: 10.5445/IR/1000129739
Veröffentlicht am 16.02.2021
Originalveröffentlichung
DOI: 10.1002/chem.202003402
Scopus
Zitationen: 2
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Katalyseforschung und -technologie (IKFT)
Publikationstyp Zeitschriftenaufsatz
Publikationsmonat/-jahr 02.2021
Sprache Englisch
Identifikator ISSN: 0947-6539, 1521-3765
KITopen-ID: 1000129739
Erschienen in Chemistry - a European journal
Verlag Wiley
Band 27
Heft 7
Seiten 2332–2341
Vorab online veröffentlicht am 30.11.2020
Schlagwörter chirality; helicene; hexabenzocoronene; naphthalene; π-extension
Nachgewiesen in Scopus
Web of Science
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