Iridium(iii)-catalyzed one-pot synthesis of planar chiral emissive materials through C–H activation

Abstract

In this study, we detail the synthesis of a series of 4-aryl-5-carboxy[2.2]paracyclophanes (3a–3s) through the C(sp²)–H activation of 4-carboxy[2.2]paracyclophane, representing the first instance of such a catalytic procedure. This protocol demonstrates remarkable versatility, accommodating various α-substituted pyridine boronates bearing electron-donating groups, thiophene boronate, and aryl boronates. Utilizing these [2.2]paracyclophane derivatives, we construct a series of organic emissive molecules, which exhibit moderate quantum yields and large Stokes shifts both in solution and solid-state, stabilizing the potential of the solid-state PMMA film as solid-state emissive material. Additionally, the planar chiral compounds derived from this synthetic series exhibit efficient chiroptical properties. These collective findings underscore the unprecedented synthesis of these 4-aryl-5-carboxy[2.2]paracyclophanes and their potential applications in the advancing of solid-state lighting and the exploring chiroptical materials.