For the oxa-Michael addition/elimination equilibrium ( 1-R–OH ⇌ 1-R-tricyc , governed by p K a 2 ), the p K a 2 values displayed an increasing trend with increasing electron-donating character of the R group: 11.09 (−NO 2 ), 11.30 (−F), 11.40 (−Br), 11.35 (−H), and 12.02 (−NH 2 ) while the kinetics studies under pH 13.5 buffer disclosed that higher rate constants for electron withdrawing substitute and lower rate constants for the electron donating groups ( Figure S8 ).
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Programmable Multi-State Fluorescence Switching on a Dynamic Molecular System via Sequential Dynamic Covalent Chemistry and Applications.
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