Chlorodiphenyltin(IV) dithiocarbamate complexes as chemodosimeters and host for anions and neutral compounds in solution

Abstract The chlorodiphenyltin(IV) dithiocarbamate complexes 1 – 5 with general formula {(Ph 2 SnCl) dtc } ( dtc  = R 1 R 2 NCS 2 − ; 1 , R 1  = Bn, R 2  = 9-anthrylmethyl; 2 , R 1  = Bn, R 2  = 9-phenanthrylmethyl; 3 , R 1  = Bn, R 2  = 1-pyrenylmethyl; 4 , R 1  = 1-naphthylmethyl, R 2  = 1-pyrenylmethyl; 5, R 1  = R 2 1-pyrenylmethyl) have been tested as host for anions and neutral amines in acetonitrile by spectrophotometric UV/Vis titrations. In addition, the titrations of the complexes 1 and 5 were studied in chloroform by 1 H and 119 Sn NMR spectroscopy. It was found that anions as acetate, benzoate, and dihydrogen phosphate cause a displacement of the dithiocarbamate ligands of metallic center independently of the aromatic nature of the substituents on the nitrogen atom functioning as chemodosimeters in which the indicator is displaced. However, some aliphatic amines and aromatic methylene amines and its aromatic analogs can act as guests with binding constants in the range of 10 3 to 10 6  M −1 . Also, in these cases compound 5 functions as chemodosimeter without displacement of the indicator. According to 1 H, 13 C, 119 Sn NMR data and using DFT (B3LYP) and Poisson–Boltzmann (PB) to model the solvent, structures of the complexes are proposed in which the hydrophobic and π–π interactions are suggested as the dominant interactions.