Supramolecular chemistry is a rich subset of chemistry whereby molecules interact extensively through directional non-covalent interactions. Since its advent, polymer scientists have taken advantage of this macromolecular self-assembly technique by means of hydrogen-bonding and/or metal coordination. These materials have been studied fervently for their structure-property relationships, tunability, and potential for responsiveness to multiple stimuli. In the present work, we focus on the use of dipolar interactions as a means to promote assembly. Current literature suggests that stacking behavior in highly conjugated small molecules can become increasingly stabilized as assemblies grow and induce greater dipole-dipole interactions. Specifically, the synthesis of 4,5-diamino-3,6-dibromophthalonitrile (DADBPN) has been reported to have a high dipole moment of 12.3 ± 0.4 D, but has yet to be implemented as a means to induce supramolecular chain extension. By adding a clickable alkyne moiety to DADBPN, chain-end modification of a telechelic polymer was made possible via azido-alkyne click chemistry. Self-assembly behavior, morphology, and structure-property relationships of these polymers in solvent annealed thin films will be discussed as well as various compositional parameters including polymer nature, molecular weights, and dispersity.

Self-assembly behavior of telechelic polymers with high-dipole moment chain ends

255th National Meeting (2018)

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