Title: Controlled Self-Assembly of C-3-Symmetric Hexa-peri-hexabenzocoronenes with Alternating Hydrophilic and Hydrophobic Substituents in Solution, in the Bulk, and on a Surface
Authors: Feng, Xinliang ×
Pisula, Wojciech
Kudernac, Tibor
Wu, Dongqing
Zhi, Linjie
De Feyter, Steven
Muellen, Klaus #
Issue Date: Apr-2009
Publisher: Amer chemical soc
Series Title: Journal of the American Chemical Society vol:131 issue:12 pages:4439-4448
Abstract: In this work, we introduce a class of C-symmetric hexa-peri-hexabenzocoronenes (HBCs) 1 with alternating hydrophilic and hydrophobic substituents to achieve control over the self-assembly of discotic nanographene molecules. Our studies show that the following structural parameters and experimental conditions are essential for tailoring the formation of the liquid-crystalline phase in the bulk as well as the self-assembly in solution and on surfaces: (1) steric demand of alkyl and alkylphenyl substituents; (2) noncovalent hydrophilic-hydrophobic interactions of the substituents; and (3) processing conditions, such as the type and mixture of solvents of different polarities along with the nature of the surface. The substitution of HBC with linear alkyl side chains possessing less steric demand (1b) leads to high crystallinity in the bulk solid state and at the liquid-solid interface, and the additional feature of alternating hydrophilic and hydrophobic substituents promotes a high aggregation tendency in polar/apolar solvent mixtures. In contrast, bulky branched alkyl chains (1a) and alkylphenyl substituents (1c) induce liquid crystallinity over the whole temperature range measured. While la does not show pronounced self-assembly in solution, compound 1c displays, even at high temperatures, aggregation in polar/apolar solution due to the intermolecular "locking" of peripheral phenyl groups. After solution deposition on a surface, distinct fiber formation is observed for the HBC derivatives, which is related to the solution self-assembly behavior. The present work provides further insight into the molecular design and self-assembly of discotic nanographene materials.
ISSN: 0002-7863
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Imaging and Photonics
× corresponding author
# (joint) last author

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