Rosidah Shardin, S. S. Tan, M. Kassim
2017
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Abstract
Derivatives of N-bromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea were successfully synthesized from the reaction of 1,10phenanthroline with x-bromobenzoylisothiocyanate (x = ortho, meta and para) to give phen-o-BrBT, phen-m-BrBT and phen-pBrBT, respectively. The molecular structures of the derivatives compounds were elucidated based on the crystal structure of Nbromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea, CHNS elemental analysis, mass spectrometry, spectroscopic data (infrared, ultraviolet-visible, nuclear magnetic resonance and luminescence) and cyclic voltammetry.The mass spectrum show similar m/z values at 460.9 and 260.0, which represent the molecular ions for [(phen-x-BrBT)-Na] and [BrBT], respectively. The presence of a v(NH) (3389-3599 cm) and the disappearance of ν(NH2) bands from 1,10-phenanthroline-5-amine indicate the formation of the N-bromobenzoyl-N'-(1,10-phenanthrolin-5-yl)thiourea. Attachment of a Br atom to the benzoyl moiety reduced the stretching frequency of C=O group by >20 cm compared with phen-BT ligand. The compounds exhibit two π→π* bands at 231 and 269270 nm for the phenanthroline and benzoyl moieties, respectively. The resonance for N-H proton appeared at δ = 11.53-12.49 ppm. In addition, C resonance signals for C=S and C=O groups were recorded at around 182 and 167.39-169.08 ppm, respectively. The synthesis and effect of a Br substitution on the structural and luminescence properties of N-bromobenzoyl-N'(1,10-phenanthrolin-5-yl)thiourea derivatives are presented and discussed in this study.