Mimicking Nature’s ability to create well-defined functional materials is a major goal in polymer chemistry. Recently there have been extensive efforts to design synthetic polymer chains that fold to form discrete single-chain polymer nanoparticles (SCPNs). This process is reminiscent of the folding of proteins to form three-dimensional tertiary structures. Since protein functionality is derived from this precise folding of the backbone into a well-defined structure, it would be of great interest to achieve control over the folding of a synthetic polymer. We present a polyacrylate-based polymer that folds as a result of the self-assembly of pendant benzene-1,3,5-tricarboxamide (BTA) units via threefold hydrogen bonding. A proportion of these BTA units are permanently anchored to the polymer backbone, while another proportion are dynamically attached via thermally reversible Diels-Alder adducts. By controlling the environmental parameters of the reversible reaction, such as the polarity of the solvent and the temperature, the anchoring position of the dynamically-attached BTA units is proposed to adapt to reach a more thermodynamically stable structure. This change in sequence as a response to the environment could have an influence on the folding of the SCPN and potentially on its physical properties.

Molecular adaptation of SCPNs <i>via</i> tandem dynamic Diels-Alder chemistry and BTA self-assembly

254th National Meeting (2017)

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Molecular adaptation of SCPNs via tandem dynamic Diels-Alder chemistry and BTA self-assembly