Inverse electron demand Diels-Alder reactions between s-tetrazines and strained dienophiles have numerous applications in fluorescent labeling of biomolecules.H erein, we investigate the effect of the dienophile on the fluorescence enhancement obtained upon reaction with at etrazinequenched fluorophore and study the possible mechanisms of fluorescence quenching by both the tetrazine and its reaction products.T he dihydropyridazine obtained from reaction with astrained cyclooctene shows aresidual fluorescence quenching effect, greater than that exerted by the pyridazine arising from reaction with the analogous alkyne.L inear and ultrabroadband two-dimensional electronic spectroscopye xperiments reveal that resonance energy transfer is the mechanism responsible for the fluorescence quenching effect of tetrazines, whereas am echanism involving more intimate electronic coupling,l ikely photoinduced electron transfer,i sr esponsible for the quenchinge ffect of the dihydropyridazine.T hese studies uncover parameters that can be tuned to maximize fluorogenic efficiency in bioconjugation reactions and reveal that strained alkynes are better reaction partners for achieving maximum contrast ratio.
Inverse electron demand Diels-Alder reactions between s-tetrazines and strained dienophiles have numerous applications in fluorescent labeling of biomolecules.H erein, we investigate the effect of the dienophile on the fluorescence enhancement obtained upon reaction with at etrazine-quenched fluorophore and study the possible mechanisms of fluorescence quenching by both the tetrazine and its reaction products.T he dihydropyridazine obtained from reaction with astrained cyclooctene shows aresidual fluorescence quenching effect, greater than that exerted by the pyridazine arising from reaction with the analogous alkyne.L inear and ultrabroadband two-dimensional electronic spectroscopye xperiments reveal that resonance energy transfer is the mechanism responsible for the fluorescence quenching effect of tetrazines, whereas am echanism involving more intimate electronic coupling,l ikely photoinduced electron transfer,i sr esponsible for the quenching effect of the dihydropyridazine.T hese studies uncover parameters that can be tuned to maximizef luorogenic efficiency in bioconjugation reactions and reveal that strained alkynes are better reaction partners for achieving maximum contrast ratio.
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