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We report the stabilisation of pyromellitic diimide molecules by core-functionalisation with cationic phosphonium groups of different cone angles. The phosphonium groups lower the energy of the lowest unoccupied molecular orbitals and the corresponding reduction potentials by at most 0.75 V for the second reduction. Both cyclic voltammetry and computational studies using density functional theories point to the trend of more stabilisation as the phosphonium cone angles get smaller. We also isolated a PMDI phosphonium ylide, obtained its x-ray crystal structure, and studied its lack of reactivity in methylation and wittig reactions.
Kim, Min Ji, "Functionalising Pyromellitic Diimide with Phosphonium Groups" (2019). Chemistry Honors Projects. 25.
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