Naphthalene diimides are useful molecules in a variety of molecular assemblies, including those highlighted by the 2016 Nobel Prize in Chemistry, due to their stability and relatively electron poor core. Importantly, chemistry developed over the past few years allows for systematic derivatization of the NDI core, which affects the electronics of this molecule. NDI derivatives can be combined with electron-rich aromatics, where they act as electron acceptors, driving self-assembly to form donor-acceptor columnar liquid crystals (DACLCs). This research focuses on synthesizing NDI molecules with either 0, 2, or 4 core substituents, fluorine was used in this case, for systematic study of the effect of core functionality on DACLC structure and properties. Two pathways for the synthesis of substituted NDIs emerged and will be discussed.

Synthesis of naphthalene diimides with varying core substitutions for use in donor acceptor aromatic interactions

253rd National Meeting (2017)

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