Synthesis, characterization and theoretical and fluorescence emission microscopy studies of new Pd/Pt-cyclopropa[60]fullerene complexes: Application of Taguchi method for optimization of parameters in Suzuki-Miyaura reaction

The reactions of unsymmetric phosphorus ylides of the type [Ph2P(CH2)(n)PPh2C(H)C(O)C6H4-p-CN] (n=1 (Y-1); n=2 (Y-2)) with C-60 and M(dba)(2) (M=Pd or Pt; dba=dibenzylideneacetone) are reported. Based on the various coordination modes of these ylides in complexation, the following new Pd/Pt-cyclopropa[60]fullerene complexes were obtained: P,C-coordinated [((2)-C-60)Pd((2)-Y-1)] (1) and [((2)-C-60)Pt((2)-Y-1)] (2) complexes and P-coordinated [((2)-C-60)Pd(Y-2)(2)] (3) and [((2)-C-60)Pt(Y-2)(2)] (4) complexes. These compounds were characterized using Fourier transform infrared, UV-visible and NMR (H-1, C-13 and P-31) spectroscopies and scanning electron microscopy. Furthermore, cytotoxicity studies showed that nanoparticles of these complexes can be used as non-toxic labels for cellular imaging application. Also energy decomposition analysis results revealed that the percentage contribution of E-elec in total interaction energy is considerably larger than that of E-orb. Thus, in all complexes the ((2)-C-60)M(Y-1) bond is considerably more electrostatic in nature than the ((2)-C-60)M(Y-1) bond. Finally, by application of the Taguchi method for optimization of parameters in Suzuki-Miyaura reaction, the catalytic activity of Pd complexes 1 and 3 was investigated in the cross-coupling reaction of various aryl chlorides with phenylboronic acid. According to analysis of variance results, solvent has the highest F value and it has high contribution percentage (36.75%) to the yield of Suzuki-Miyaura reaction.