The Synthesis and Electronic Properties of Responsive, [pi]-Conjugated lsoindolinone Small Molecules

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University of New Brunswick


Isoindolinone ring systems are found in a variety of natural products and synthetic pharmaceuticals, but also possess interesting electronic properties that can be used in organic electronics. Incorporation of isoindolinone units into oligomer targets with extended conjugation for applications such as organic photovoltaics (OPV) and organic field-effect transistors (OFETs) requires a versatile and facile synthetic method. We have developed a nucleophilic fluoride-induced cyclization between an amide and a neighbouring substituted alkyne to form an isoindolinone, which allows facile variation of the conjugation length and overall molecular structure, providing the opportunity to develop many isoindolinone derivatives with extended [pi]-conjugation. We have synthesized a variety of isoindolinone-containing compounds that exhibit responsiveness to both acid and UV light by isomerization between the E and Z form at the alkene. Preliminary switching studies using two promising targets have been completed toward the development of multi-stable switches.