Synthesis of {242}- and {323}-p-Octiphenyls

Baudry, Yoann Cyril; Ronan, Dawn; Jeannerat, Damien; Matile, Stefan

doi:10.1002/hlca.200490198

Scientific article

English

Synthesis of {242}- and {323}-p-Octiphenyls

Contributors

Baudry, Yoann Cyril; Ronan, Dawn; Jeannerat, Damien; Matile, Stefan

Published in

Helvetica chimica acta, vol. 87, no. 9, p. 2181-2189

Publication date

2004

Abstract

The introduction of rigid-rod molecules as privileged scaffolds has opened routes to otherwise problematic supramolecular architecture like artificial ß-barrels and functional supramolecules covering pores, hosts, sensors, and catalysts. The usefulness of p-oligophenyls for the construction of functional barrel-stave architecture has, however, been limited by uniform substitution along the rigid-rod scaffold. The objective of this report is to overcome this obstacle for the synthesis of p-octiphenyls with orthogonally protected carboxylic acid groups along the rigid-rod scaffold. In the reported {242}-p-octiphenyl 1, the two peripheral arene moieties carry carboxylic acid groups protected as benzyl esters, whereas the four central carboxylic acid groups are protected orthogonally as tert-butyl esters (Scheme 2). The complementary orthogonal protection of the three peripheral and the two central arenes is achieved in the {323}-p-octiphenyl 2 (Scheme 3). The realized {242}- and {323}-p-octiphenyls 1 and 2, respectively, provide a complete set for the general access to refined rigid-rod barrel-stave architecture with maximized functional plasticity. The need for resolution-enhanced (aliased) HMBC 2D-NMR spectroscopy to characterize these refined oligomers is described in the following publication in this issue of Helv. Chim. Acta.

UNIGE affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

BAUDRY, Yoann Cyril et al. Synthesis of {242}- and {323}-p-Octiphenyls. In: Helvetica chimica acta, 2004, vol. 87, n° 9, p. 2181–2189. doi: 10.1002/hlca.200490198

Article

Identifiers

PID : unige:7834
DOI : 10.1002/hlca.200490198

Journal ISSN

0018-019X

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Synthesis of {242}- and {323}-p-Octiphenyls

Contributors

Published in

Publication date

Abstract

UNIGE affiliation entities

Citation (ISO format)

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Journal ISSN

Technical informations

Creation

First validation

Update

Status update

Last indexation