Tailored Synthesis of N-Substituted peri-Xanthenoxanthene Diimide (PXXDI) and Monoimide (PXXMI) Scaffolds

Andrea Sciutto, Andrey Berezin, Matteo Lo Cicero, Tanja Miletić, Antoine Stopin, Davide Bonifazi
J. Org. Chem., 2018, 83 (22), pp 13787–13798
DOI: 10.1021/acs.joc.8b02076


The tailored synthesis of homo (A2) and hetero (AB) N-substituted peri-xanthenoxanthene diimides (PXXDIs) and peri-functionalized PXX monoimides (PXXMIs) from 3-hydroxy naphthalic anhydride is described. As A2-type PXXDIs could be synthesized in one step, AB-type PXXDIs and PXXMIs were prepared through a modular approach capitalizing on sequential Suzuki coupling, imidation, and Pummerer reactions with very high yields. In view of their potential applications as organic semiconductors, self-organization studies were performed through liquid deposition on surfaces, depicting the formation of islands, needles, and rods.

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