Unveiling the Synthetic Potential of 1,3,5-Tri(10H-phenothiazin-10-yl)benzene-Based Optoelectronic Material: A Metal-Free and Recyclable Photocatalyst for Sequential Functionalization of C(sp2)–H Bonds,ACS Applied Materials & Interfaces

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Unveiling the Synthetic Potential of 1,3,5-Tri(10H-phenothiazin-10-yl)benzene-Based Optoelectronic Material: A Metal-Free and Recyclable Photocatalyst for Sequential Functionalization of C(sp2)–H Bonds
ACS Applied Materials & Interfaces ( IF 8.3 ) Pub Date : 2022-06-27 , DOI: 10.1021/acsami.2c08766
Cen Zhou ₁ , Rui Wang ₂ , Lang Gao ₂ , Xiaozhou Huang ₂ , Xiao Zhang ₂

Affiliation

1,3,5-Tri(10H-phenothiazin-10-yl)benzene (3PTZ) is endowed with unique redox and photoresponsive characteristics and has been utilized as a p-type redox center for organic battery cathode material and a room-temperature phosphorescence (RTP) material, respectively. Conversely, its exploration in other research fields, particularly organic synthesis, remains unknown. Here, we demonstrate that 3PTZ-POP synthesized via cross-linking of 3PTZ is capable of harvesting visible-light photons and selectively converting solar energy to chemical energy. Specifically, 3PTZ-POP functions as a metal-free and recyclable photocatalyst to promote the sequential C(sp²)–H functionalizations of N-arylacrylamides with readily available trifluoromethylsulfonyl chloride as the radical precursor. An array of 3,3-disubstituted 2-oxindoles bearing a pharmaceutically important CF₃ moiety are delivered in moderate to excellent yields under mild and sustainable conditions.

中文翻译：

揭示 1,3,5-三（10H-吩噻嗪-10-基）苯基光电材料的合成潜力：一种用于 C(sp2)-H 键顺序功能化的无金属和可回收光催化剂

1,3,5-三(10 H-吩噻嗪-10-基)苯(3PTZ)具有独特的氧化还原和光响应特性，已被用作有机电池正极材料的p型氧化还原中心和室温磷光（RTP）材料，分别。相反，它在其他研究领域的探索，特别是有机合成，仍然未知。在这里，我们证明了通过 3PTZ 交联合成的 3PTZ-POP 能够收集可见光光子并选择性地将太阳能转化为化学能。具体而言，3PTZ-POP 作为一种无金属且可回收的光催化剂，可促进N的顺序 C(sp ² )-H 官能化-芳基丙烯酰胺，具有易得的三氟甲基磺酰氯作为自由基前体。一系列带有药学上重要的 CF ₃部分的 3,3-二取代 2-羟吲哚在温和和可持续的条件下以中等至优异的产率递送。

更新日期：2022-06-27

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