Self-assembly of photofunctional cylindrical nanostructures based on perylene-3,4: 9,10-bis(dicarboximide)

Louise E. Sinks, Boris Rybtchinski, Masanori Iimura, Brooks A. Jones, Andrew J. Goshe, Xiaobing Zuo, David M. Tiede, Xiyou Li, Michael R Wasielewski

Research output: Contribution to journalArticle

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Abstract

A perylene-3,4:9,10-bis(dicarboximide)-based electron donor-acceptor monomer was designed to self-assemble using the synergistic effects of π-π stacking, microsegregation, and hydrogen bonding. The resulting aggregates were characterized in solution by small-angle X-ray scattering (SAXS), while the solid-state structure was probed by X-ray diffraction, transmission electron microscopy, and scanning electron microscopy. The solution-phase assemblies were found to consist of 12 monomers arranged in either a face-to-face stacked pair of hydrogen-bonded hexagonal arrays or a two-turn helix. The SAXS data do not allow a clear distinction between these two cyclic motifs. These cyclic arrays grow to lengths of about 1 μm and form bundles of cylindrical structures in the solid phase. Aggregation is solvent dependent, with methylcyclohexane inducing aggregation and tetrahydrofuran disrupting it. The solution-phase photophysics of the dodecamer were probed by UV-vis, time-resolved fluorescence, and femtosecond transient absorption spectroscopies, revealing that formation of the dodecamer introduces an ultrafast electron-transfer pathway that is not present in the monomer.

Original languageEnglish
Pages (from-to)6295-6303
Number of pages9
JournalChemistry of Materials
Volume17
Issue number25
DOIs
Publication statusPublished - Dec 13 2005

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Perylene
Self assembly
Nanostructures
Monomers
X ray scattering
Agglomeration
Electrons
Absorption spectroscopy
Hydrogen
Hydrogen bonds
Fluorescence
Transmission electron microscopy
X ray diffraction
Scanning electron microscopy

ASJC Scopus subject areas

  • Materials Chemistry
  • Materials Science(all)

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Self-assembly of photofunctional cylindrical nanostructures based on perylene-3,4 : 9,10-bis(dicarboximide). / Sinks, Louise E.; Rybtchinski, Boris; Iimura, Masanori; Jones, Brooks A.; Goshe, Andrew J.; Zuo, Xiaobing; Tiede, David M.; Li, Xiyou; Wasielewski, Michael R.

In: Chemistry of Materials, Vol. 17, No. 25, 13.12.2005, p. 6295-6303.

Research output: Contribution to journalArticle

Sinks, Louise E. ; Rybtchinski, Boris ; Iimura, Masanori ; Jones, Brooks A. ; Goshe, Andrew J. ; Zuo, Xiaobing ; Tiede, David M. ; Li, Xiyou ; Wasielewski, Michael R. / Self-assembly of photofunctional cylindrical nanostructures based on perylene-3,4 : 9,10-bis(dicarboximide). In: Chemistry of Materials. 2005 ; Vol. 17, No. 25. pp. 6295-6303.
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