Effect of Multiple Interactions on Face-On vs Edge-On Configurations of Butadiyne-Bridged Octa­dehydro­dibenzo[12]annulene Derivatives at the Liquid/Graphite Interface

We investigated the self-assembled monolayers of octa­dehydro­dibenzo[12]­annulene (DBA) derivatives to see the effect of multiple intermolecular interactions on the formation of face-on vs edge-on configurations of planar compounds having weak core to core interactions at the liquid/graphite interf...

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Veröffentlicht in:Journal of physical chemistry. C 2015-07, Vol.119 (28), p.15977-15981
Hauptverfasser: Guo, Zhaoqi, Tahara, Kazukuni, Inukai, Koji, Takeda, Hiroshi, Kouno, Masahiro, Iritani, Kohei, Tobe, Yoshito
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Sprache:eng
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Zusammenfassung:We investigated the self-assembled monolayers of octa­dehydro­dibenzo[12]­annulene (DBA) derivatives to see the effect of multiple intermolecular interactions on the formation of face-on vs edge-on configurations of planar compounds having weak core to core interactions at the liquid/graphite interfaces by means of scanning tunneling microscopy (STM). A DBA derivative having an N-dodecylamide chain at each end of the π-core formed face-on mode self-assemblies at the interfaces of both 1-phenyloctane (PO) and 1-octanoic acid (OA) and graphite. On the other hand, another DBA having both N-dodecylamide chains and methoxymethyl groups formed an edge-on mode self-assembly at the PO/graphite interface. However, at the OA/graphite interface, it formed a face-on mode self-assembly due to the solvent–molecule hydrogen bonds which suppress the intermolecular interactions. These results indicate that by multiple interactions between substituents the edge-on mode of self-assembly can be stabilized, rendering the otherwise unfavorable pattern be formed preferentially.
ISSN:1932-7447
1932-7455
DOI:10.1021/acs.jpcc.5b02569