Metalation of N-methyl-1,3-thiazoline-2-thione followed by reaction with elemental S or Se affords a simple and efficient approach to N-methyl-1,3-thiazoline-2-thione-4,5-dithiolate (Me-thiazdt) and the diselenolate (Me-thiazds) analogue. In the presence of metal II centers such as Zn, Ni, and Pd these ligands afford the corresponding dianionic dithiolene and diselenolene complexes. The Ni and Pd dianionic complexes are easily oxidized into the monoanionic species. Complexes were isolated and characterized by single-crystal X-ray crystallography. Most often a substitutional S/N-Me disorder is observed, attributable to the square-planar trans complexes disordered on two positions or coexistence of both cis and trans isomers on inversion centers. Monoanionic complexes exhibit a strong NIR absorption band with epsilon values up to 33 750 M(-1) cm(-1).

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