Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 18, Pages 6806-6816Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201500026
Keywords
dipole-dipole interactions; macrocycles; scanning probe microscopy; self-assembly; surface analysis
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Funding
- JSPS-KAKENHI [21245012, 24350046, 26620063]
- Fund of Scientific Research - Flanders (FWO), KU Leuven [GOA 11/003]
- Belgian Federal Science Policy Office [IAP-7/05]
- JSPS
- FWO under the Japan-Belgium Research Cooperative Program
- European Research Council under the European Union [340324]
- Grants-in-Aid for Scientific Research [15H02164, 21245012] Funding Source: KAKEN
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We have systematically investigated the self-assembled monolayers of seven bimolecular mixtures of square-shaped pyridinophanes and cyclophanes bearing alkoxy or alkoxycarbonyl substituents in the presence of the tropylium ion as a marker of pyridinophanes at liquid/graphite interfaces by means of scanning tunnelling microscopy (STM). The purpose of this work was to elucidate the mixing behaviour of these macrocycles highlighting the formation of one-or two-dimensionally ordered square tilings consisting of alternating alignments of different macrocycles as a result of attractive dipole-dipole or hydrogen-bonding interactions; four co-crystals differing in the dimensionality of the ordering of pyridinophane and cyclophane were observed. The different modes of interaction between the functional groups (ether or carbonyl group) in the side-chains of the pyridinophanes and cyclophanes lead to the formation of co-crystals with dimensionally different orderings of the two macrocycles. These observations revealed that a slight modification of the molecular structure may dramatically change the mixing behaviour and structures of the co-crystals.
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