Title: Synthesis of dehydrobenzo[18]annulene derivatives and formation of self-assembled monolayers: Implications of core size on alkyl chain interdigitation
Authors: Tahara, Kazukuni ×
Johnson, Charles A
Fujita, Takumi
Sonoda, Motohiro
De Schryver, Frans
De Feyter, Steven
Haley, Michael M
Tobe, Yoshito #
Issue Date: Sep-2007
Publisher: Amer chemical soc
Series Title: Langmuir vol:23 issue:20 pages:10190-10197
Abstract: The synthesis of a series of dodecadehydrotribenzo[18]annuiene ([18]DBA) derivatives is reported, together with their steady-state absorption and fluorescence properties. The main focus, though, is on the self-assembly of these compounds at the liquid-solid interface as investigated with scanning tunneling microscopy (STM), highlighting the effect of alkyl chain orientation and alkyl chain length on the molecular ordering. Owing to the large triangular T-electron system of the [18]DBAs, two different types of alkyl chain orientation are observed. The observed changes in the monolayer networks upon elongation of the alkyl chains are attributed to the increased van der Waals interactions between molecules and substrate. The effect of the core size on the alkyl chain orientation and, as a result, the monolayer structure is discussed in relation to the results obtained previously for triangularly-shaped dehydrobenzo [12]annulene ([12]DBA) derivatives and triphenylene derivatives. A guideline for substituent spacing allowing control of molecular alignment for large planar g-electron systems utilizing directional alkyl chain interdigitation is also discussed.
ISSN: 0743-7463
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Imaging and Photonics
× corresponding author
# (joint) last author

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