Regioselectivity in the Scholl Reaction: Mono and Double [7]Helicenes
Mohammad Mosharraf Hossain, Khushabu Thakur, Marat R. Talipov, Sergey V. Lindeman, Saber Mirzaei, Rajendra Rathore
Abstract
We employed the density functionaly theory (DFT)-predicted regioselectivity of the intramolecular Scholl reaction in phenanthrene and dibenzo[g,p]chrysene frameworks to obtain π-extended mono and double [7]helicenes, respectively. The formation of these helical structures occurs despite the buildup of a large strain energy up to 30 kcal/mol compared with their most stable isomers. The twisted and strained structures were characterized and analyzed by experimental (NMR, UV–vis, emission, electrochemistry, and single-crystal X-ray diffraction) techniques and were further supported by DFT calculations.
Topics & Concepts
ChryseneChemistryRegioselectivityIntramolecular forceDensity functional theoryHelicenePhenanthreneCrystallographyDiffractionCrystal structureComputational chemistryStereochemistryMoleculeCatalysisOrganic chemistryPhysicsOpticsSynthesis and Properties of Aromatic CompoundsFullerene Chemistry and ApplicationsDNA and Nucleic Acid Chemistry