A simple and efficient synthetic route for syntheses of 2-2’-bipyrazine (bpz) derivatives is described starting with 2-chloropyrazine and 2-methyl-4-carboxypyrazine resulting in 2,2’-bipyrazine, 4-methyl-2,2’-bipyrazine (mbpz), 4,4’-dimethyl-2,2’-bipyrazine (dmbpz), 4,4’-dicarboxy-2,2’-bipyrazine (dcbpz) and 2-pyridyl-2-pyrazine (pypz). The bidentate ligands were ligated with Re (I) and Ru (II) to make dyes useful for harvesting solar energy and for potential therapeutic agents. The complexes to be described are: [Re(bpz)(dppm)(CO)3]+, [{Re(bpz)(CO)3}2(dppe)]2+, Re(CO)3(dcbpz)Cl, Re(CO)3(dmbpz)Cl, Re(CO)3(mbpz)Cl, Re(CO)3(pypz)Cl and [Ru(bpz)2(dcbpz)]2+ (where dppm is diphenylphosphinomethane, dppe is diphenylphosphinoethane). The bridged Re (I) complex was synthesized using diphenylphosphinoethane (dppe). These complexes were characterized by 1H NMR, mass spectra and elemental analyses. The Re (I) and Ru (II) complexes absorb in the near UV region of the spectrum and emit near 600 nm when excited into the lowest energy absorption band. Emission lifetimes determined in a glassy matrix or in solution varied from 100 to 400 ns.

Simple, efficient synthetic route to 2-2’-bipyrazine derivatives from bromo-pyrazine for making rhenium and ruthenium dyes

254th National Meeting (2017)

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