Electrospray Mass Spectrometry to Study Combinatorial iClick Reactions and Multiplexed Kinetics of [Ru(N3)(NN)(terpy)]PF6 with Alkynes of Different Steric and Electronic Demand

Inorganic chemistry(2023)

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Abstract
In a combinatorial approach, a family of ruthenium-(II) azido complexes [Ru(N3)(N perpendicular to N)(terpy)]PF6 with terpy = 2,2 ':6 ',2 ''-terpyridine and N perpendicular to N as a bidentate chelator derived from 2,2 '-biypridine and its 4,4 '-disubstituted derivatives, 2,2 '- bipyrimidine, and 1,10-phenanthroline were reacted with different internal and terminal alkynes to give access to a total of 7 x 7 = 49 triazolato complexes in a room-temperature catalyst-free iClick reaction. The reactants were mixed in a repurposed high-performance liquid chromatography (HPLC) autosampler, and the reaction progress was monitored by direct injection into an electrospray mass spectrometer. The ratio of the peak intensities of [Ru(N3)(N perpendicular to N)(terpy)]+ and [Ru(triazolato)(N perpendicular to N)(terpy)]+ was converted to a colored heat map for facile visual inspection of the conversion ratio. By automated multiple injections of the reaction mixture in fixed time intervals and plotting peak intensities over reaction time, pseudo-first-order rate constants were easily determined. Finally, nonoverlapping isotope patterns of the azido starting materials and triazolato products enabled multiplexed parallel determination of rate constants for four different ruthenium(II) azido complexes from a single sample vial, thereby reducing experiment time by 75%.
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