An efficient protocol was developed for the synthesis of π-extended isocoumarins and polycyclic aromatic hydrocarbons based on the oxidative coupling of aromatic carboxylic acids with internal alkynes catalyzed by (cyclopentadienyl)rhodium complexes. The coupling chemoselectivity strongly depends on whether Cp or the methylated Cp* ligands are used. The pentamethyl derivative [Cp*RhCl2 ]2 predominantly gives isocoumarins, while the non-methylated complex [CpRhI2 ]n produces naphthalene derivatives. The polyaromatic carboxylic acids (such as 1-naphthoic acid, 1-pyrenecarboxylic acid, fluorene-1-carboxylic acid, and dibenzofuran-4-carboxylic acid) are suitable for this approach. A mixture of Cp*H/RhCl3 can be used as a catalyst instead of [Cp*RhCl2 ]2 . The structures of 3,4-diphenylindeno[1,2-h]isochromen-1(11H)-one and 7,10-dimethyl-8,9-diphenylbenzo[pqr]tetraphene were determined by X-ray diffraction. In addition, the optical properties of the prepared compounds were studied. 7,8-Diphenyl-10H-phenaleno[1,9-gh]isochromen-10-one was employed as an emissive layer for OLED manufacturing. The OLED emits yellow-green light with a maximum intensity 1740 cd ⋅ m-2 at 15 V.

中文翻译：

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Cp-配体甲基化对铑（III）催化炔烃芳族羧酸环化的影响：异香豆素和PAHs的合成，用于有机发光器件。

基于芳族羧酸与（环戊二烯基）铑配合物催化的内部炔烃的氧化偶联，开发了一种高效的合成π-扩展的异香豆素和多环芳烃的方案。偶联化学选择性很大程度上取决于是否使用Cp或甲基化的Cp *配体。五甲基衍生物[Cp * RhCl2] 2主要产生异香豆素，而未甲基化的络合物[CpRhI2] n产生萘衍生物。聚芳族羧酸（例如1-萘甲酸，1-吡啶羧酸，芴-1-羧酸和二苯并呋喃-4-羧酸）适用于该方法。Cp * H / RhCl3的混合物可以代替[Cp * RhCl2] 2用作催化剂。3,4-二苯基茚并[1,2-h]异色素n-1（11H）-one和7,10-二甲基-8的结构 通过X射线衍射测定9-二苯基苯并[pqr]四苯基。另外，还研究了所制备化合物的光学性质。7,8-二苯基-10H-苯并[1,9-gh]异色素n-10-one被用作OLED制造的发光层。OLED在15 V时发出最大强度为1740 cd⋅m-2的黄绿色光。