Synthesis and Two-Dimensional Chiral Self-Assembly of Oxygen-Incorporated Dibenzo[ <i>hi</i> , <i>st</i> ]ovalene

The oxygen-incorporated analogue of dibenzo[<i>hi,st</i>]ovalene (O-DBOV), namely, <i>peri</i>-bisxanthenoanthanthrene, was synthesized through the oxidative cycloetherification of a dihydroxy-substituted precursor, using a catalytic amount of KI and <i>tert</i>-butyl hydroperoxide (TBHP) as an external oxidant. O-DBOV is prochiral to have two-dimensional (2D) chirality upon interaction with solid surfaces. Notably, investigation of the self-assembled monolayers of O-DBOV on Au(111) surfaces by scanning tunneling microscopy (STM) under ultrahigh vacuum (UHV) conditions revealed the formation of 2D homochiral domains through hydrogen bonding and van der Waals interactions.