Issue 12, 2024

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
02 Apr 2024
Accepted
25 Apr 2024
First published
26 Apr 2024

Org. Chem. Front., 2024,11, 3384-3390

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

W. Liu, H. Ji, W. Duan, H. Wang, Y. Huo, X. Huang and P. Duan, Org. Chem. Front., 2024, 11, 3384 DOI: 10.1039/D4QO00582A

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