Two-Step Synthesis, Structure, and Optical Features of a Double Hetero[7]helicene
Mohamed S. H. Salem, Ahmed Sabri, Md. Imrul Khalid, Hiroaki Sasai, Shinobu Takizawa
Abstract
A novel double aza-oxa[7]helicene was synthesized from the commercially available N1,N4-di(naphthalen-2-yl)benzene-1,4-diamine and p-benzoquinone in two steps. Combining the acid-mediated annulation with the electrochemical sequential reaction (oxidative coupling and dehydrative cyclization) afforded this double hetero[7]helicene. Moreover, the structural and optical features of this molecule have been studied using X-ray crystallographic analysis, and the absorption and emission behaviors were rationalized based on DFT calculations.
Topics & Concepts
HeliceneChemistryMoleculeBenzeneDiamineElectrochemistryDouble bondStereochemistryCrystallographyCombinatorial chemistryOrganic chemistryPhysical chemistryElectrodeSynthesis and Properties of Aromatic CompoundsPhotochromic and Fluorescence ChemistryPorphyrin and Phthalocyanine Chemistry