The assembly of rigid molecular building blocks from the bottom-up provides a promising approach to fulfill an emerging need to fabricate shape-persistent nanostructures and molecular machines. In contrast to conventional, top-down patterning approaches, including photolithography, “dip-pen” nanolithography, and nano-imprint lithography, molecular self-assembly enables exquisite spatial control at the molecular scale and is not limited to 2D substrates. Moreover, organic molecular electronics have emerged as an alternative to Si-based electronic materials for building integrated devices owing to their potential applications in flexible devices and the capacity to be employed in planar configurations.<br/>Here, the synthesis and dynamic covalent assembly of sequence-specific, <i>p</i>-phenylene-ethynylene oligomers bearing pendant dynamic covalent functionalities will be examined. Conventional solid-phase synthesis will be employed for the rapid fabrication of the sequence-specific oligomers, where the repeat units will be iteratively built up from solid support via alternating Sonogashira coupling and silyl deprotection steps using trimethylsilyl-protected 1,4-ethynylphenyliodide monomers. Additionally, sequence-directed dynamic covalent assembly to generate phenylene-ethynylene-based molecular ladders will be discussed, where the specificity and stability of the double-stranded dynamic covalent oligomers are studied to elucidate the underlying effect of backbone structure, and dynamically covalent pendant groups.

Dynamic covalent assembly of sequence-specific, π-conjugated oligomers

256th National Meeting (2018)

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