Issue 10, 2006

An evaluation of the relationship between two- and three-dimensional packing in self-organised monolayers and bulk crystals of amphiphilic 2,2′:6′,2″-terpyridines

Abstract

2,2′:6′,2″-Terpyridine (tpy) ligands with pendant octadecyloxy, 4-octyloxyphenyl or 4-octadecyloxyphenyl substituents at the 4′-position have been prepared and structurally characterised. Monolayers of the compounds have been prepared on highly oriented pyrolytic graphite (HOPG) and investigated by STM. The monolayer structure corresponds to the bulk crystal structure if the latter contains planar sheets. The tpy ligands are prochiral and form homochiral domains within the monolayer, providing a spectacular visual representation of the symmetry-breaking concomitant with the formation of a monolayer.

Graphical abstract: An evaluation of the relationship between two- and three-dimensional packing in self-organised monolayers and bulk crystals of amphiphilic 2,2′:6′,2″-terpyridines

Supplementary files

Article information

Article type
Paper
Submitted
08 Jun 2006
Accepted
13 Jul 2006
First published
23 Aug 2006

New J. Chem., 2006,30, 1470-1479

An evaluation of the relationship between two- and three-dimensional packing in self-organised monolayers and bulk crystals of amphiphilic 2,2′:6′,2″-terpyridines

E. C. Constable, H.-J. Güntherodt, C. E. Housecroft, L. Merz, M. Neuburger, S. Schaffner and Y. Tao, New J. Chem., 2006, 30, 1470 DOI: 10.1039/B608136C

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