Catálogo de Investigaciones 2017-2018

CATÁLOGO DE INVESTIGACIONES | AÑO ACADÉMICO 2017-2018 49 Synthesis of Catechol and Hydroquinone Analogs for Their Applications in Self-Assembled Monolayers The purpose of this research project was synthesizing hydroquinone and catechol compounds to study their electrochemical behavior, to gain understanding about the relative strength and type of chemisorption, and to comprehend dynamics of ligands displacement at the solid- liquid interface on electrodes. It is expected that the longer the chain, the better the electrochemical behavior and higher surface coverage. The hydroquinone analogs were prepared by adding the corresponding dibromoalkane chain group (3,5,6,9 and 11) to 1,4-dimethoxybenzene in THF and under nitrogen atmosphere. Demethylation, bromine substitution, and acidification were needed to achieve the desire molecules. The pentalkylated brominated hydroquinone was synthesized with a percent yield of 71%. In addition, a benzylated group was incorporated into 1,2-dimethoxybenzene for the catechol analogs. Catechol analogs such as Bis (3,4-dihydroxyphenyl) methanone (BDHPmethanone), BDHPmethane, BDHPmethanol, were achieved with a 33%, 96%, and 21% respectively. Compound syntheses were successfully achieved with the mixture of reagents, followed by extractions, concentration under reduce pressure, and purification by silica gel chromatography. Proton nuclear magnetic resonance (1HNMR), infrared spectroscopy (IR), retardation factor, and melting point were applied. The study of these compounds will bring improvements in instruments such as electrodes, that are used to measure conductivity and biosensors for the detection of diseases. arnaldox. torreshernández, alexy m. padilla andújar, carlos echevarría, michael montalvo rivera, nicole torres colón, josé santiago mass y adalgisa batista parra puerto rico louis stokes alliance for minority participation mentor: dra. adalgisa batista parra catechol analogs hydroquinone analogs synthesis self-assembled monolayers sams