Dusold C, Platzer B, Haines P, Reger D, Jux N, Guldi DM, Hirsch A (2021)
Publication Type: Journal article
Publication year: 2021
Book Volume: 27
Pages Range: 1670-1679
Synthesis and characterization of a series of rylene-diimide substituted hexaphenylbenzenes (HPBs) is presented. The direct connection of the rylene-diimide units to the HPBs via the imide-N-position without any linkers as well as the use of naphthalene-diimides (NDIs) next to perylene-diimides (PDIs) is unprecedented. While mono-substituted products were obtained by imidization reactions with amino-HPB and the respective rylene-monoimides, key step for the formation of tri- and hexa-substituted HPBs is the Co-catalysed cyclotrimerization. Particular emphasis for physic-chemical characterization was on to the number of NDIs/PDIs per HPB and the overall substitution patterns. Lastly, Scholl oxidation conditions were applied to all HPB systems to generate the corresponding hexa-peri-hexabenzocoronenes (HBCs). Importantly, the efficiency of the transformation strongly depends on the number of NDIs/PDIs. While three rylene-diimide units already hinder the Scholl reaction, the successful synthesis of mono-substituted HBCs is possible.
APA:
Dusold, C., Platzer, B., Haines, P., Reger, D., Jux, N., Guldi, D.M., & Hirsch, A. (2021). A Functional Hexaphenylbenzene Library Comprising of One, Three, and Six Peripheral Rylene-Diimide Substituents. Chemistry - A European Journal, 27, 1670-1679. https://dx.doi.org/10.1002/chem.202004273
MLA:
Dusold, Carolin, et al. "A Functional Hexaphenylbenzene Library Comprising of One, Three, and Six Peripheral Rylene-Diimide Substituents." Chemistry - A European Journal 27 (2021): 1670-1679.
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