Synthesis of a novel metal free porphyrin dyad with excellent electronic coupling and anti-aggregating stability via strong anchoring to semiconductor through six carboxyl groups exhibiting 6.9% PCE in a truly energy generating DSSC.
We report the synthesis of a new, sulfonic acid functionalized, melamine‐based metal‐free porphyrin photocatalyst (MBMFPc) for the C−C coupling of the most unreactive aryl halides with alkenes under visible light irradiation. The ionic liquid‐based photocatalyst was characterized using various analytical techniques Proton Nuclear Magnetic Resonance (1HNMR) Spectroscopy, Carbon Nuclear Magnetic Resonance (13CNMR) Spectroscopy, Fourier Transformed Infrared Spectroscopy (FT‐IR), Energy‐dispersive X‐ray Spectroscopy (EDAX), Scanning Electron Microscope (SEM), Brunauer‐Emmett‐Teller (B.E.T) and Ultraviolet‐Visible Spectroscopy (UV‐Vis). The MBMFPc photocatalyst with noticeable Hammett acidity (0.56) and optimal bandgap of 1.44 eV was found to as an effective catalyst in the Mizoroki‐Heck coupling of inactivated aryl fluoride/chloride using 5 W LED in a homemade photoreactor under ambient conditions. The protocol comprising metal‐free green photocatalyst tolerated a variety of aliphatic/aromatic alkenes bearing different substituents afforded good to excellent yields. The role of photogenerated excitons was confirmed by scavenger studies with K2S2O8 and EDTA. The leaching test, stability, and reusability of MBMFPc photocatalyst evidenced as a perfect heterogeneous photocatalyst and afford appreciable yield (80 %) after 5 cycles. A plausible mechanism for photocatalytic C−C coupling has been proposed and described. A metal‐free acid‐functionalized ionic liquid‐based MBMFPc photocatalyst with appreciable TON (4,51,948) and TOF (22,597 h−1) could gain significant attraction as a green catalyst in the pharmaceutical industries for the synthesis of intermediates by C−C coupling using commercial aryl chlorides.
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