Abstract
Several new electroactive diquinone and dihydroquinone derivatives of calix[4]arene bearing anchor functional groups were designed, synthesized and characterized. A method for selective protection of the hydroquinone -OH groups with trimethylsilyl groups (TMS) either on lower-rim or on upper-rim was developed. Four selected molecules - with sulfide anchor groups and carboxylic anchor groups - were adsorbed onto Au(111) single crystal surface using ex-situ and insitu self-assembly methods. Adsorbed molecules were then electrochemically probed with cyclic voltammetry. All adsorbed molecules showed redox response which changed during cycling. After conditioning CVs stabilized and showed two distinct current peaks for all molecules. Synthesized and electrochemically probed molecules are of interest to: Li-ion batteries (as cathode materials and overcharge protection), beyond Li-ion batteries and redox-flow batteries.
Highlights
World energy consumption is continuously growing with electrical energy being the single largest consumer
Protected product 1b was oxidized to quinone derivative 2b and bromine was introduced to the unoccupied sites
We tried to substitute the bromine on compound 3b with thioacetyl anchor group but reaction conditions used, did not furnish desired product
Summary
World energy consumption is continuously growing with electrical energy being the single largest consumer. Batteries, being the main representative of electrochemical energy storage, will play a key role in the future energy consumption cycle. One of the revived fields is the use of redox active organic molecules in the battery systems. Redox active organic molecules are chemically divided into: organosulfur molecules, organic free radical compounds, and carbonyl compounds.. Redox active organic molecules are chemically divided into: organosulfur molecules, organic free radical compounds, and carbonyl compounds.17 The latter, having a quinone/hydroquinone as a key representative, are playing a significant role in electroactivity relevant to biochemistry, medicine and electrochemistry. Quinone derivatives were tested as cathode materials in Li-ion batteries and redox-flow batteries.. We examined several synthetic routes in order to synthesize quinone derivatives of calix[4]arene which could be bound to the electrode materials and electrochemically tested. Synthesized organic molecules were anchored to the Au(111) single crystal surface using self-assembly protocol and electrochemically probed
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