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Endo-Functionalized Cyclic Oligophenylenes: Synthesis and Complexation with a Chiral Phosphoric Acid.

ABSTRACT: The synthesis of endo-functionalized cyclic oligophenylenes in which adjacent benzene rings are perpendicular to one another is described. Annulation precursors, OH- or NH2-functionalized quinquephenyl diboronic acids, and septiphenyl dibromo compounds were systematically prepared by using a diprotected biphenyl-3,4'-diyl diboronic acid as a key compound. Four endo-functionalized cyclic oligophenylenes were synthesized by annulation of the precursors in dilute conditions through Suzuki-Miyaura cross-coupling. X-ray analysis of the macrocycle revealed the unique 1D channel packing structure formed by connecting the nanometer-sized cavity of the macrocycle. Furthermore, NH2-functionalized macrocycles could bind a chiral phosphoric acid in the cavity in CDCl3 solution.

SUBMITTER: Ono K 

PROVIDER: S-EPMC9753635 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature

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<i>Endo</i>-Functionalized Cyclic Oligophenylenes: Synthesis and Complexation with a Chiral Phosphoric Acid.

Ono Kosuke K   Tanaka Yusei Y   Sugimoto Kana K   Kinubari Shigemi S   Kawai Hidetoshi H  

ACS omega 20221128 49

The synthesis of <i>endo</i>-functionalized cyclic oligophenylenes in which adjacent benzene rings are perpendicular to one another is described. Annulation precursors, OH- or NH<sub>2</sub>-functionalized quinquephenyl diboronic acids, and septiphenyl dibromo compounds were systematically prepared by using a diprotected biphenyl-3,4'-diyl diboronic acid as a key compound. Four <i>endo</i>-functionalized cyclic oligophenylenes were synthesized by annulation of the precursors in dilute conditions  ...[more]

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