Liu Ningchao, Morimoto Hirofumi, Wu Fan, Lv Xiaojuan, Xiao Bentian, Kuzuhara Daiki, Pan Jianming, Qiu Fengxian, Aratani Naoki, Shen Zhen, Yamada Hiroko, Xue Songlin
School of Chemistry and Chemical Engineering, Jiangsu University, 301 Xuefu Road, Zhenjiang 212013, China.
Division of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma, Nara 630-0192, Japan.
Org Lett. 2022 May 27;24(20):3609-3613. doi: 10.1021/acs.orglett.2c01147. Epub 2022 May 16.
Novel 24π antiaromatic and 26π aromatic 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.
首次通过一锅法合成从无β位的联吡咯成功获得了新型的24π反芳香性和26π芳香性芳基玫瑰红。由于吡咯单元的β位没有取代基，经X射线晶体学证实，无β位的原始玫瑰红骨架具有高度平面性。光学测量表明，通过氧化还原反应，24π反芳香性和26π芳香性的无β位原始玫瑰红之间可相互转化，而在扭曲的β-十二甲基玫瑰红中未观察到这种现象。
