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.

中文翻译：

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铱(III)催化C-H活化一锅法合成平面手性发射材料

在本研究中，我们详细介绍了通过 4-羧基[2.2]对环芳烷的 C(sp ² )-H活化合成一系列 4-芳基-5-羧基[2.2]对环芳烷 ( 3a–3s ) ，这代表了第一个这种催化过程的一个例子。该方案表现出显着的多功能性，可容纳各种带有给电子基团的α-取代吡啶硼酸酯、噻吩硼酸酯和芳基硼酸酯。利用这些[2.2]对环芳烷衍生物，我们构建了一系列有机发光分子，它们在溶液和固态中均表现出中等的量子产率和大的斯托克斯位移，稳定了固态PMMA薄膜作为固态发光材料的潜力。此外，源自该合成系列的平面手性化合物表现出高效的手性光学特性。这些集体发现强调了这些 4-芳基-5-羧基[2.2]对环芳烷的前所未有的合成及其在推进固态照明和探索手性光学材料方面的潜在应用。