Versatile bisethynyl[60]fulleropyrrolidine scaffolds for mimicking artificial light-harvesting photoreaction centers

Adrian Kremer, Emerance Bietlot, Alberto Zanelli, Joanna M. Malicka, Nicola Armaroli, Davide Bonifazi

Research output: Contribution to journalArticle

Abstract

Fullerene-based tetrads, triads, and dyads are presented in which [60]fulleropyrrolidine synthons are linked to an oligo(p-phenyleneethynylene) antenna at the nitrogen atom and to electron-donor phenothiazine (PTZ) and/or ferrocene (Fc) moieties at the α carbon of the pyrrolidine cycle through an acetylene spacer. Cyclic voltammetry and UV/ Vis absorption spectra evidence negligible ground-state electronic interactions among the subunits. By contrast, strong excited-state interactions are detected upon selective light irradiation of the antenna (UV) or of the fullerene scaffold (Vis). When only PTZ is present as electron donor, photoinduced electron transfer to the fullerene unit is unambiguously detected in benzonitrile, but this is not the case when Fc is part of the multicomponent system. These results suggest that Fc is a formidable energy transfer quencher and caution should be used in choosing it as electron donor to promote efficient charge separation in multicomponent arrays.

Original languageEnglish
Pages (from-to)1108-1117
Number of pages10
JournalChemistry: A European Journal
Volume21
Issue number3
DOIs
Publication statusPublished - 12 Jan 2015

Fingerprint

Fullerenes
Scaffolds
Electrons
Antennas
Acetylene
Excited states
Energy transfer
Ground state
Cyclic voltammetry
Absorption spectra
Nitrogen
Carbon
Irradiation
Atoms
ferrocene
phenothiazine

Keywords

  • Energy transfer
  • Fullerenes
  • Light harvesting
  • Spectroelectrochemistry
  • Synthetic methods

Cite this

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abstract = "Fullerene-based tetrads, triads, and dyads are presented in which [60]fulleropyrrolidine synthons are linked to an oligo(p-phenyleneethynylene) antenna at the nitrogen atom and to electron-donor phenothiazine (PTZ) and/or ferrocene (Fc) moieties at the α carbon of the pyrrolidine cycle through an acetylene spacer. Cyclic voltammetry and UV/ Vis absorption spectra evidence negligible ground-state electronic interactions among the subunits. By contrast, strong excited-state interactions are detected upon selective light irradiation of the antenna (UV) or of the fullerene scaffold (Vis). When only PTZ is present as electron donor, photoinduced electron transfer to the fullerene unit is unambiguously detected in benzonitrile, but this is not the case when Fc is part of the multicomponent system. These results suggest that Fc is a formidable energy transfer quencher and caution should be used in choosing it as electron donor to promote efficient charge separation in multicomponent arrays.",
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Versatile bisethynyl[60]fulleropyrrolidine scaffolds for mimicking artificial light-harvesting photoreaction centers. / Kremer, Adrian; Bietlot, Emerance; Zanelli, Alberto; Malicka, Joanna M.; Armaroli, Nicola; Bonifazi, Davide.

In: Chemistry: A European Journal, Vol. 21, No. 3, 12.01.2015, p. 1108-1117.

Research output: Contribution to journalArticle

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AU - Armaroli, Nicola

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