Premium
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
Author(s) -
Sabounchei Seyyed Javad,
Badpa Khadijeh,
Hashemi Ali,
Salehzadeh Sadegh,
Maleki Farahnaz,
Hosseinzadeh Leila
Publication year - 2018
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.4382
Subject(s) - chemistry , phenylboronic acid , aryl , catalysis , suzuki reaction , palladium , crystallography , coupling reaction , fluorescence , fullerene , nuclear chemistry , organic chemistry , alkyl , physics , quantum mechanics
The reactions of unsymmetric phosphorus ylides of the type [Ph 2 P(CH 2 ) n PPh 2 C(H)C(O)C 6 H 4 ‐ 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 [(η 2 ‐C 60 )Pd(κ 2 ‐Y 1 )] ( 1 ) and [(η 2 ‐C 60 )Pt(κ 2 ‐Y 1 )] ( 2 ) complexes and P‐coordinated [(η 2 ‐C 60 )Pd(Y 2 ) 2 ] ( 3 ) and [(η 2 ‐C 60 )Pt(Y 2 ) 2 ] ( 4 ) complexes. These compounds were characterized using Fourier transform infrared, UV–visible and NMR ( 1 H, 13 C and 31 P) 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 Δ E elec in total interaction energy is considerably larger than that of Δ E orb . Thus, in all complexes the (η 2 ‐C 60 )M(Y 1 ) bond is considerably more electrostatic in nature than the (η 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.