Oligoboroxine-based architectures

Ono, Kosuke; Iwasawa, Nobuharu

doi:10.1007/s10847-021-01074-6

Cited by 7 publications

(2 citation statements)

References 85 publications

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“…We designed hexagonal-shaped cyclic oligophenylenes 1 in which adjacent benzene rings are perpendicular to one another by using o -methylated p -phenylene units ( Figure 1 ). 9 The macrocycle 1 has a well-defined nanometer-sized cavity surrounded by six p -phenylene rings. This nonplanar arrangement of the phenylene units and multiply introduced tert -butyl groups at the peripheral positions are expected to increase the solubility due to the inhibition of the π-stacking of macrocycles.…”

Section: Resultsmentioning

confidence: 99%

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

et al. 2022

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The synthesis of endo-functionalized cyclic oligophenylenes in which adjacent benzene rings are perpendicular to one another is described. Annulation precursors, OH-or NH 2functionalized 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, NH 2 -functionalized macrocycles could bind a chiral phosphoric acid in the cavity in CDCl 3 solution.

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Section: Resultsmentioning

confidence: 99%

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

et al. 2022

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“…Boroxines also dissociate easily into three molecules of boronic acid or boronic ester by hydrolysis or alcoholysis. 7 The quantitative construction of a series of nanometer-sized cage structures using the simple dehydration of the appropriately designed diboronic acids has been reported. 8 Against this background, herein, a simple synthetic method for macrocyclic compounds that are based on a reversible boroxine formation was developed (Fig.…”

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Boroxine template for macrocyclization and postfunctionalization

2022

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Structural Interconversion Based on Intramolecular Boroxine Formation

Ono

Sawanaga

Onodera

et al. 2023

Chemistry A European J

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A novel structural interconversion unit based on intramolecular boroxine formation has been developed. A macrocyclic triboronic acid consisting of three phenylboronic acid units linked by covalent linkers preferentially underwent intramolecular rather than intermolecular boroxine formation, resulting in a quantitative formation of tricyclic boroxine. This structural transformation was accompanied by changes in the polarity, flexibility, and size of the molecule. Dynamic interconversion between the macrocyclic triboronic acid and the tricyclic boroxine was achieved by simple heating/cooling, whereas no boroxine formation occurred upon heating when three boronic acid units were not connected by linkers. Thermodynamic analysis revealed that the entropic advantage of the intramolecular boroxine formation process resulted in these unique features. The entropically stabilized tricyclic boroxine also shows high stability with respect to hydrolysis.

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Oligoboroxine-based architectures

Cited by 7 publications

References 85 publications

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

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

Boroxine template for macrocyclization and postfunctionalization

Structural Interconversion Based on Intramolecular Boroxine Formation

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