Folding-induced modulation of excited-state dynamics in an oligophenylene-ethynylene-tethered spiral perylene bisimide aggregate

Minjung Son, Benjamin Fimmel, Volker Dehm, Frank Würthner, Dongho Kim

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Abstract The excited-state photophysical behavior of a spiral perylene bisimide (PBI) folda-octamer (F8) tethered to an oligophenylene-ethynylene scaffold is comprehensively investigated. Solvent-dependent UV/Vis and fluorescence studies reveal that the degree of folding in this foldamer is extremely sensitive to the solvent, thus giving rise to an extended conformation in CHCl3 and a folded helical aggregate in methylcyclohexane (MCH). The exciton-deactivation dynamics are largely governed by the supramolecular structure of F8. Femtosecond transient absorption (TA) in the near-infrared region indicates a photoinduced electron-transfer process from the backbone to the PBI core in the extended conformation, whereas excitation power- and polarization-dependent TA measurements combined with computational modeling showed that excitation energy transfer between the unit PBI chromophores is the major deactivation pathway in the folded counterpart. Switching by Stacking: Solvent-induced folding of an oligophenylene-ethynylene-tethered perylene bisimide (PBI) folda-octamer is found to play an important role in controlling its exciton deactivation pathways. Excitation energy-transfer and photoinduced electron-transfer processes are found to occur in a nearly switchable manner depending on the supramolecular conformation of the foldamer.

Original languageEnglish
Pages (from-to)1757-1767
Number of pages11
JournalChemPhysChem
Volume16
Issue number8
DOIs
Publication statusPublished - 2015 Jun 1

Fingerprint

Excited states
folding
Modulation
deactivation
Conformations
modulation
Excitation energy
Energy transfer
excitation
electron transfer
energy transfer
excitons
Electrons
Chromophores
Scaffolds
chromophores
Fluorescence
Polarization
Infrared radiation
fluorescence

All Science Journal Classification (ASJC) codes

  • Atomic and Molecular Physics, and Optics
  • Physical and Theoretical Chemistry

Cite this

Son, Minjung ; Fimmel, Benjamin ; Dehm, Volker ; Würthner, Frank ; Kim, Dongho. / Folding-induced modulation of excited-state dynamics in an oligophenylene-ethynylene-tethered spiral perylene bisimide aggregate. In: ChemPhysChem. 2015 ; Vol. 16, No. 8. pp. 1757-1767.
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Folding-induced modulation of excited-state dynamics in an oligophenylene-ethynylene-tethered spiral perylene bisimide aggregate. / Son, Minjung; Fimmel, Benjamin; Dehm, Volker; Würthner, Frank; Kim, Dongho.

In: ChemPhysChem, Vol. 16, No. 8, 01.06.2015, p. 1757-1767.

Research output: Contribution to journalArticle

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AU - Kim, Dongho

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AB - Abstract The excited-state photophysical behavior of a spiral perylene bisimide (PBI) folda-octamer (F8) tethered to an oligophenylene-ethynylene scaffold is comprehensively investigated. Solvent-dependent UV/Vis and fluorescence studies reveal that the degree of folding in this foldamer is extremely sensitive to the solvent, thus giving rise to an extended conformation in CHCl3 and a folded helical aggregate in methylcyclohexane (MCH). The exciton-deactivation dynamics are largely governed by the supramolecular structure of F8. Femtosecond transient absorption (TA) in the near-infrared region indicates a photoinduced electron-transfer process from the backbone to the PBI core in the extended conformation, whereas excitation power- and polarization-dependent TA measurements combined with computational modeling showed that excitation energy transfer between the unit PBI chromophores is the major deactivation pathway in the folded counterpart. Switching by Stacking: Solvent-induced folding of an oligophenylene-ethynylene-tethered perylene bisimide (PBI) folda-octamer is found to play an important role in controlling its exciton deactivation pathways. Excitation energy-transfer and photoinduced electron-transfer processes are found to occur in a nearly switchable manner depending on the supramolecular conformation of the foldamer.

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