Abstract
We report the preparation, using electrochemical and solid-phase synthesis, and characterisation of a 26 member library of 13 dihydroxybenzene derivatives covalently attached to glassy carbon through ethylenediamine (EDA) and C
6H
4CH
2NH
linkers. First, Boc-protected EDA or Boc–NHCH
2C
6H
4 were electrochemically attached to the GC surface. After Boc-deprotection, dimethoxybenzoyl chlorides were coupled to the EDA and C
6H
4CH
2NH
linkers using solid-phase synthesis followed by deprotection of the methoxy groups to give the corresponding dihydroxybenzene compounds. Surface coverage and electrochemical parameters of the dihydroxybenzene modified electrodes were evaluated in parallel using cyclic voltammetry. The mid-peak potentials,
E
mp, and surface coverages for the 13 dihydroxybenzene derivatives were found to be independent of the choice of linker. The mid-peak potentials of the immobilised dihydroxybenzene derivatives varied between 0.0 and 260 mV vs. SCE and their surface coverages varied between 0.07 and 1.1 nmol cm
−
2
, depending on the pattern of substitution of the dihydroxybenzene ring. The electrocatalytic activities of the library were evaluated for mediation of NADH oxidation, and the
ortho-dihydroxybenzene derivatives were found to have higher catalytic activity.