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Abstract: A new stepwise self-assembly procedure is described for the preparation of functional cyclodextrin-modified electrodes. The approach is based on the formation of alkanethiol/lipoylamide- beta-cyclodextrin monolayers with the thiol component responsible for blocking of the electrode surface and lipoylamide-beta-cyclodextrin molecules-for controlled opening of the access of the electroactive probe to the electrode. Functionalization of the electrode is achieved by means of a new cyclodextrin derivative-mono(6-deoxy-6-lipoylamide)-per- 2,3,6-0-acetyl-beta-cyclo-dextrin-prepared in the peracetyl form and deacetylated directly on the electrode surface following the cyclodextrin self-assembly. The progress of deacetylation was monitored by the MALDI MS technique. Deacetylation caused opening of the active sites toward solution probes. The response toward ferrocene was found to be highly improved when ferrocene was added to the solution following self-assembly of cyclodextrin but prior to the thiol self-assembly step (imprinting method). The proposed synthesis and sequential monolayer formation scheme lead to well- organized and stable modified electrode surfaces with improved sensitivity toward solution species compared to other procedures of electrode modification with the cyclodextrin derivatives