Self-assembly of supramolecular light-harvesting arrays from covalent multi-chromophore perylene-3,4

9,10=bis(dicarboximide) building blocks

Michael J. Ahrens, Louise E. Sinks, Boris Rybtchinski, Wenhao Liu, Brooks A. Jones, Jovan M. Giaimo, Alexy V. Gusev, Andrew J. Goshe, David M. Tiede, Michael R Wasielewski

Research output: Contribution to journalArticle

251 Citations (Scopus)

Abstract

We report on two multi-chromophore building blocks that self-assemble in solution and on surfaces into supramolecular light-harvesting arrays. Each building block is based on perylene-3,4:9,10-bis(dicarboximide) (PDI) chromophores. In one building block, N-phenyl PDI chromophores are attached at their para positions to both nitrogens and the 3 and 6 carbons of pyromellitimide to form a cross-shaped molecule (PI-PDI4). In the second building block, N-phenyl PDI chromophores are attached at their para positions to both nitrogens and the 1 and 7 carbons of a fifth PDI to produce a saddle-shaped molecule (PDI5). These molecules self-assemble into partially ordered dimeric structures (PI-PDI4)2 and (PDI5)2 in toluene and 2-methyltetrahydrofuran solutions with the PDI molecules approximately parallel to one another primarily due to π-π interactions between adjacent PDI chromophores. On hydrophobic surfaces, PDI5 grows into rod-shaped nanostructures of average length 130 nm as revealed by atomic force microscopy. Photoexcitation of these supramolecular dimers in solution gives direct evidence of strong π-π interactions between the excited PDI chromophore and other PDI molecules nearby based on the observed formation of an excimer-like state in

Original languageEnglish
Pages (from-to)8284-8294
Number of pages11
JournalJournal of the American Chemical Society
Volume126
Issue number26
DOIs
Publication statusPublished - Jul 7 2004

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Perylene
Chromophores
Self assembly
Light
Nitrogen
Carbon
Molecules
Nanostructures
Atomic Force Microscopy
Toluene
Photoexcitation
Dimers
Atomic force microscopy

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Self-assembly of supramolecular light-harvesting arrays from covalent multi-chromophore perylene-3,4 : 9,10=bis(dicarboximide) building blocks. / Ahrens, Michael J.; Sinks, Louise E.; Rybtchinski, Boris; Liu, Wenhao; Jones, Brooks A.; Giaimo, Jovan M.; Gusev, Alexy V.; Goshe, Andrew J.; Tiede, David M.; Wasielewski, Michael R.

In: Journal of the American Chemical Society, Vol. 126, No. 26, 07.07.2004, p. 8284-8294.

Research output: Contribution to journalArticle

Ahrens, Michael J. ; Sinks, Louise E. ; Rybtchinski, Boris ; Liu, Wenhao ; Jones, Brooks A. ; Giaimo, Jovan M. ; Gusev, Alexy V. ; Goshe, Andrew J. ; Tiede, David M. ; Wasielewski, Michael R. / Self-assembly of supramolecular light-harvesting arrays from covalent multi-chromophore perylene-3,4 : 9,10=bis(dicarboximide) building blocks. In: Journal of the American Chemical Society. 2004 ; Vol. 126, No. 26. pp. 8284-8294.
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