Ribbon-Type Boron-Doped Polycyclic Aromatic Hydrocarbons: Conformations, Dynamic Complexation and Electronic Properties.

Abstract

Molecular ribbons (MRs), one-dimentional topological polycyclic aromatic hydrocarbons (PAHs), are of importance for synthetic chemistry and material sciences. Herein, we disclose an effective strategy to develop boron-doped MRs, i.e. photochemical cyclization on conjugated organoboranes for rapid π-extension. A series of ribbon-type boron-doped PAHs that own multiple cove edges were synthesized using Mallory photoreaction in solution. Two of them feature isomeric C68 B2 π-skeletons with 2.2 nm in length, thus representing a new kind of boron-doped MRs. The boron atoms endow them with sufficient Lewis acidity, and notably, the formed Lewis acid-base adducts based on boron-doped MRs display the photo-induced dual-dissociation behavior in the excited state and thus photochromism property. Moreover, despite of the highly contorted topological conformations, their potential utility as organic semiconductor was demonstrated by fabrication of organic field-effect transistors.