Syntheses of ligands containing two and three 2,2'-(bisamino)diphenyl ether units designed for molecular self-assembly on lithiation

Peter R. Ashton; Bernd Hörner; Oldrich Kocian; Stephan Menzer; Andrew J P White; J. Fraser Stoddart; David J. Williams

doi:10.1055/s-1996-4319

Syntheses of ligands containing two and three 2,2'-(bisamino)diphenyl ether units designed for molecular self-assembly on lithiation

Peter R. Ashton, Bernd Hörner, Oldrich Kocian, Stephan Menzer, Andrew J P White, J. Fraser Stoddart^*, David J. Williams

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article

13 Scopus citations

Abstract

The syntheses of polyamines containing two or three 2,2'-(bisamino)diphenyl ether units linked together, designed for self-assembly following lithiation, are reported. The X-ray crystal structures of two of the bis[2,2'-(bisamido)diphenyl ethers] are described. The ligand, which is linked by an ethylene glycol spacer, exhibits a coiled conformation constrained by intramolecular hydrogen bonds and supplemented by [CH-π] interactions. The ligand, which is linked by a more rigid bridge, containing a paraphenylene unit, displays a stretched conformation stabilised by intramolecular hydrogen bonds and intramolecular T-type aromatic-aromatic edge-to-face interactions.

Original language	English (US)
Pages (from-to)	930-940
Number of pages	11
Journal	Synthesis
Issue number	8
DOIs	https://doi.org/10.1055/s-1996-4319
State	Published - Jan 1 1996

Keywords

2,2'-(bisamino)diphenyl ether
lithium amides
self-assembly

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-1996-4319

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Ashton, P. R., Hörner, B., Kocian, O., Menzer, S., White, A. J. P., Stoddart, J. F., & Williams, D. J. (1996). Syntheses of ligands containing two and three 2,2'-(bisamino)diphenyl ether units designed for molecular self-assembly on lithiation. Synthesis, (8), 930-940. https://doi.org/10.1055/s-1996-4319

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abstract = "The syntheses of polyamines containing two or three 2,2'-(bisamino)diphenyl ether units linked together, designed for self-assembly following lithiation, are reported. The X-ray crystal structures of two of the bis[2,2'-(bisamido)diphenyl ethers] are described. The ligand, which is linked by an ethylene glycol spacer, exhibits a coiled conformation constrained by intramolecular hydrogen bonds and supplemented by [CH-π] interactions. The ligand, which is linked by a more rigid bridge, containing a paraphenylene unit, displays a stretched conformation stabilised by intramolecular hydrogen bonds and intramolecular T-type aromatic-aromatic edge-to-face interactions.",

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AU - Ashton, Peter R.

AU - Hörner, Bernd

AU - Kocian, Oldrich

AU - Menzer, Stephan

AU - White, Andrew J P

AU - Stoddart, J. Fraser

AU - Williams, David J.

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