A recent trend in the design of polymers is the incorporation of reversible chemistry, where damaged material can independently repair itself. This type of �self healing� material includes supramolecular polymers that contain systems of multiple hydrogen bonds such as ureidopyrimidinone (Upy), Figure 1. This system, originally developed by R.J. Sijbsma and E.W. Meijer, has a dimerizing constant of 6 x 107m-1 and is commercially developed under the trade name SupraB1.Our hypothesis is that by adding a dimethylaminophenyl moiety to serve as a redox center when attached to Meijer's Upy 4 H-bond system, we can decrease the binding strength of the dimer upon oxidation. The binding strength of the Upy 4 H-bond array is inherent in not only the number of hydrogen bonds each unit possesses but the sequence for which they are arranged. Hydrogen bond donors (D) as well as hydrogen bonding acceptors (A) when arranged next to each other can benefit from secondary binding interactions that contribute to the overall binding strength. Previous cyclic voltammetry (CV) studies conducted in our lab with an electroactive urea, indicate that as oxidation occurs, the urea N-H bond connected to the redox center, becomes acidic enough that proton transfer an acceptor (A) occurs. We think that this change in proton ownership will disrupt and possibly weaken the binding strength as the DDAA arrangement changes to an ADDA arrangement upon oxidation.This presentation will cover CV scans based on concentration and scan rate dependence as the H-bond array is oxidized. Spectroelectrochemistry as well as digital CV simulations will also be presented. Figure 1. Structure of dimerized 4-H bond array, showing arrangement of proton donor (D) and proton acceptor (A). R2 is the dimethylaminophenyl moiety that adds redox functionality to structure2.

Electrochemical characterization of an electroactive ureidopyrimidinone derivative, Meijer's four hydrogen bond array containing a dimethylaminophenylurea redox center

248th National Meeting (2014)

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