Synthesis of Planar <i>meso</i>-Aryl Rosarins: A Reversible Antiaromatic/Aromatic Interconversion
Ningchao Liu, Hirofumi Morimoto, Fan Wu, Xiaojuan Lv, Bentian Xiao, Daiki Kuzuhara, Jianming Pan, Fengxian Qiu, Naoki Aratani, Zhen Shen, Hiroko Yamada, Songlin Xue
Abstract
aryl rosarins were successfully obtained for the first time from β-free bipyrrole through a one-pot synthesis. Because of the absence of substituents at the β-positions of the pyrrole units, the β-free pristine rosarin backbones were highly planar, as confirmed using X-ray crystallography. Optical measurements indicated interconversion between 24π antiaromatic and 26π aromatic β-free pristine rosarin via redox reactions, which was not observed in distorted β-dodecamethyl rosarin.
Topics & Concepts
AntiaromaticityChemistryArylPyrroleAromaticityPlanarRedoxMoleculeOrganic chemistryComputer graphics (images)AlkylComputer sciencePorphyrin and Phthalocyanine ChemistryPhotochromic and Fluorescence ChemistryPhotosynthetic Processes and Mechanisms