The cellular entry pathways of synthetic delivery materials are closely related to the surface properties of the carriers. Conjugated polymer (CPs) have been used as a delivery vehicle for gene delivery owing to their excellent photophysical and biophysical properties. The hydrophobic and rigid rod conjugated backbone make CPs ideal for controlling self-assembly structures. Previously we have shown incorporation of a small amount of flexible unit along the backbone induces unique self-assembly structures. To examine the role of the conjugated backbone length on the self-assembly, we have designed a phenyleneethylene conjugated trimer containing acrylate end groups at the both ends, and polymerized by reacting flexible non-conjugated thiols using the thiol-ene addition reaction. The shortest fluorescent unit, the trimer, was selected to investigate the self-assembly structures by monitoring the photophysical properties of the trimer.  Positive side chain was introduced to form ionic complex with negatively charged nucleic acid. We successfully synthesized phenyleneethylene trimer-containing thiol-ene polymer at high yields. In this presentation, synthesis, self-assembly structures, and the cellular behaviors of the polymers will be discussed. We expect to demonstrate how the trimer-containing polymer enhances the cellular interaction and delivery efficiency through unique self-assembly structures.

Synthesis of fluorescent phenyleneethynylene trimer-containing polymer

253rd National Meeting (2017)

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