S-Shaped Helical Singlet Diradicaloid and Its Transformation to Circumchrysene via a Two-Stage Cyclization

• DOI: 10.1021/jacs.3c11585
• Publication Date: 2024-04-03T12:42:14Z
• Authors: Jinlian Hu; Qin Xiang; Xiaoqi Tian; Lei Ye; Yanpei Wang; Yong Ni; Xing Chen; Yuxia Liu; Guang Chen; Zhe Sun
• Keywords: Helicene; Quantum yield; Diradical

Polycyclic hydrocarbons with diradical and polyradical characters usually display unique reactivities in ring-cyclization reactions. However, such reactions are rarely used to construct π-extended polycyclic aromatic hydrocarbons. Here, we describe the synthesis of an S-shaped doubly helical singlet diradicaloid compound its facile transformation into unprecedented circumchrysene via a two-stage ring cyclization, which includes: (1) eletrocylization from precursor (2) Scholl reaction. The reaction mechanism was investigated through