Karki Sumitra, Jalife Said, Wang Xiqu, Lin Yun-Hsien, Wu Judy I, Miljanić Ognjen Š
Department of Chemistry, University of Houston, United States of America.
Faculty of Chemical Engineering, Industrial University of Ho Chi Minh City, Vietnam.
Chemistry. 2024 Dec 5;30(68):e202402913. doi: 10.1002/chem.202402913. Epub 2024 Oct 16.
Two new partially fluorinated dehydrobenzannulenes have been prepared by inter- and intramolecular oxidative homocoupling of diyne precursors. These systems contain fluorinated and nonfluorinated arene rings in a desymmetrized non-alternant arrangement. Both macrocycles are roughly planar and organize into extended columns in the solid state. The assembly of these columns is mediated by the combination of dispersion interactions, slipped [π⋅⋅⋅π] stacking interactions of the perfluorinated rings with each other, and their association with the nonfluorinated rings in the molecules of the neighboring macrocycles. These results suggest that partial fluorination of dehydrobenzannulenes can serve as a versatile motif for their assembly into columnar superstructures.
