The dynamic covalent chemistry of mono- and bifunctional boroxoaromatics

Douglas Philp; L M Greig; Alexandra Martha Zoya Slawin; M H Smith

doi:10.1016/j.tet.2006.12.034

The dynamic covalent chemistry of mono- and bifunctional boroxoaromatics

Douglas Philp, L M Greig, Alexandra Martha Zoya Slawin, M H Smith

Research output: Contribution to journal › Article › peer-review

Abstract

10-Hydroxy-10,9-boroxophenanthrene reacts rapidly and reversibly with both benzylic and alkane diols in non-polar solvents. The formation of 2:1 adducts between the boroxoaromatic and the diols is favoured. The diol component of the adduct can be exchanged readily and rapidly by treatment of the boroxoaromatic-diol adduct with an alternative diol in solution at room temperature. This reversible covalent chemistry would appear to be ideal for the dynamic assembly of more complex superstructures. However, attempts to extend this dynamic equilibrium to the assembly of macrocycles using the bifunctional boroxoaromatic 5,9-dihydroxy-5,9-dibora-4,10-dioxopyrene failed as a result of changes in the reactivity of the boron centre in the bifunctional boron-containing compound. (c) 2006 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	2391-2401
Number of pages	13
Journal	Tetrahedron
Volume	63
Issue number	11
DOIs	https://doi.org/10.1016/j.tet.2006.12.034
Publication status	Published - 12 Mar 2007

Keywords

self-assembly
molecular recognition
aromatic compounds
dynamic covalent chemistry
reversible reactions
CROSS-COUPLING REACTIONS
HYDROGEN-BONDING MOTIF
COMBINATORIAL LIBRARIES
BIOLOGICAL PRINCIPLES
MOLECULAR RECOGNITION
THERMODYNAMIC CONTROL
CINCHONA ALKALOIDS
BORROMEAN RINGS
SOLID-STATE
HELICATE

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10.1016/j.tet.2006.12.034

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title = "The dynamic covalent chemistry of mono- and bifunctional boroxoaromatics",

abstract = "10-Hydroxy-10,9-boroxophenanthrene reacts rapidly and reversibly with both benzylic and alkane diols in non-polar solvents. The formation of 2:1 adducts between the boroxoaromatic and the diols is favoured. The diol component of the adduct can be exchanged readily and rapidly by treatment of the boroxoaromatic-diol adduct with an alternative diol in solution at room temperature. This reversible covalent chemistry would appear to be ideal for the dynamic assembly of more complex superstructures. However, attempts to extend this dynamic equilibrium to the assembly of macrocycles using the bifunctional boroxoaromatic 5,9-dihydroxy-5,9-dibora-4,10-dioxopyrene failed as a result of changes in the reactivity of the boron centre in the bifunctional boron-containing compound. (c) 2006 Elsevier Ltd. All rights reserved.",

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author = "Douglas Philp and Greig, {L M} and Slawin, {Alexandra Martha Zoya} and Smith, {M H}",

year = "2007",

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AU - Philp, Douglas

AU - Greig, L M

AU - Slawin, Alexandra Martha Zoya

AU - Smith, M H

PY - 2007/3/12

Y1 - 2007/3/12

N2 - 10-Hydroxy-10,9-boroxophenanthrene reacts rapidly and reversibly with both benzylic and alkane diols in non-polar solvents. The formation of 2:1 adducts between the boroxoaromatic and the diols is favoured. The diol component of the adduct can be exchanged readily and rapidly by treatment of the boroxoaromatic-diol adduct with an alternative diol in solution at room temperature. This reversible covalent chemistry would appear to be ideal for the dynamic assembly of more complex superstructures. However, attempts to extend this dynamic equilibrium to the assembly of macrocycles using the bifunctional boroxoaromatic 5,9-dihydroxy-5,9-dibora-4,10-dioxopyrene failed as a result of changes in the reactivity of the boron centre in the bifunctional boron-containing compound. (c) 2006 Elsevier Ltd. All rights reserved.

AB - 10-Hydroxy-10,9-boroxophenanthrene reacts rapidly and reversibly with both benzylic and alkane diols in non-polar solvents. The formation of 2:1 adducts between the boroxoaromatic and the diols is favoured. The diol component of the adduct can be exchanged readily and rapidly by treatment of the boroxoaromatic-diol adduct with an alternative diol in solution at room temperature. This reversible covalent chemistry would appear to be ideal for the dynamic assembly of more complex superstructures. However, attempts to extend this dynamic equilibrium to the assembly of macrocycles using the bifunctional boroxoaromatic 5,9-dihydroxy-5,9-dibora-4,10-dioxopyrene failed as a result of changes in the reactivity of the boron centre in the bifunctional boron-containing compound. (c) 2006 Elsevier Ltd. All rights reserved.

KW - self-assembly

KW - molecular recognition

KW - aromatic compounds

KW - dynamic covalent chemistry

KW - reversible reactions

KW - CROSS-COUPLING REACTIONS

KW - HYDROGEN-BONDING MOTIF

KW - COMBINATORIAL LIBRARIES

KW - BIOLOGICAL PRINCIPLES

KW - MOLECULAR RECOGNITION

KW - THERMODYNAMIC CONTROL

KW - CINCHONA ALKALOIDS

KW - BORROMEAN RINGS

KW - SOLID-STATE

KW - HELICATE

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U2 - 10.1016/j.tet.2006.12.034

DO - 10.1016/j.tet.2006.12.034

M3 - Article

SN - 0040-4020

VL - 63

SP - 2391

EP - 2401

JO - Tetrahedron

JF - Tetrahedron

IS - 11

ER -

The dynamic covalent chemistry of mono- and bifunctional boroxoaromatics

Abstract

Keywords

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