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Unveiling the Synthetic Potential of 1,3,5-Tri(10 H -phenothiazin-10-yl)benzene-Based Optoelectronic Material: A Metal-Free and Recyclable Photocatalyst for Sequential Functionalization of C(sp 2 )-H Bonds.

Cen ZhouRui WangLang GaoXiaozhou HuangXiao Zhang
Published in: ACS applied materials & interfaces (2022)
1,3,5-Tri(10 H -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(sp 2 )-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 CF 3 moiety are delivered in moderate to excellent yields under mild and sustainable conditions.
Keyphrases
  • visible light
  • room temperature
  • ionic liquid
  • cystic fibrosis
  • water soluble
  • high resolution
  • high throughput
  • human health
  • risk assessment
  • electron transfer
  • ion batteries