5 bromo 2 thiophenecarboxaldehyde

Potassium hydroxide was purchased from J.T. Baker (León, GTO., Mexico), 4-bromophenylacetonitrile was obtained from Alfa Aesar. Tetrakis(triphenylphosphine)palladium (Pd(PPh₃)₄), palladium (II) acetate (Pd(OAc)₂), 4-(N,N-diphenylamine)-1-phenylboronic acid, 4-bromotriphenylamine, 2,2-dimethylpropionic acid, 2-thienylacetonitrile, 5-bromo-2-thiophenecarboxaldehyde, 2-thiophenecarboxaldehyde and 1,3-dibromo-5-(2-ethylhexyl)-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione, were purchased from Sigma-Aldrich (Toluca, Mexico). The other reagents and solvents were purchased from Karal (León, GTO., Mexico). All reagents and chemicals were used without further purification unless stated otherwise. The potassium pivalate (PIVOK) was synthesized according to the literature [58 (link)].

4-Trifluoromethylphenylboronic acid, 4-(dimethylamino)phenylboronic
acid, o-phenylenediamine, 2-aminothiophenol, 4-(trifluoromethyl)benzyl
bromide, 5-bromo-2-thiophenecarboxaldehyde, potassium triflate, trifluoroacetic
acid, cesium carbonate, potassium carbonate, sodium bisulfite, tetrakis(triphenylphosphine)palladium(0),
and bis(triphenylphosphine)palladium(II) chloride were obtained from
Sigma-Aldrich (Madrid, Spain). IrCl₃ was obtained from
Johnson Matthey. Deuterated solvents were obtained from Euriso-top.
The purities ≥95% of the synthesized complexes used for biological
evaluation were determined by RP-HPLC.

Pyrrole, 4-bromobenzaldehyde, dichloromethane (DCM), methanol (MeOH), high purity grade silica gel (35–60 mesh particle size, thin layer chromatography (TLC) plates, sodium acetate, 5-bromo-2-thiophenecarboxaldehyde, indium(III) chloride, tetraphenylporphyrin (H₂TPP), zinc tetraphenylporphyrin (ZnTPP) and gallium (III) chloride were purchased from Sigma Aldrich (Munich, Germany). Hexane, propionic acid, sodium hydrogen carbonate, acetic acid and zinc acetate were purchased from Loba Chemie PVT Ltd, Mumbai, India. Toluene and ethyl acetate were purchased from Fisher Scientific, Leicestershire, UK. Distilled water was obtained from an ultrapure filtration system (Millipore, resistivity 18 mΩ cm⁻¹). TiO₂ P25 was purchased from Univar Canada.