Evaluation of energy transfer in perylene-cored anthracene dendrimers

Takahashi, Masaki; Morimoto, Hironao; Miyake, Kentaro; Yamashita, Mitsuji; Kawai, Hideki; Sei, Yoshihisa; Yamaguchi, Kentaro

doi:10.1039/b606215f

Cited by 30 publications

(21 citation statements)

References 14 publications

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“…Perylene and its analogues [1] are an interesting class of polyaromatic hydrocarbons (PAH) that are investigated for diverse applications including organic solar cells [2], fluorescence labeling [3], molecular sensors [4], and molecular electronics [5]. Perylene diimides have been the most studied perylene derivatives [6–7] because of the electron accepting properties of the π-system, which results from the electron withdrawing carbonyl substituents [8].…”

Section: Introductionmentioning

confidence: 99%

The photophysical characterisation of novel 3,9-dialkyloxy- and diacyloxyperylenes

et al. 2011

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The fundamental photophysical properties of three symmetrically substituted 3,9-perylene analogues were examined in a diverse range of solvents. All three compounds exhibited solvent-dependent fluorescence quantum yield, which was lower than that of perylene or its diimides. Whilst the absence of a large excited state dipole moment suggests that there is no preferential charge accumulation in one side of the molecules, the data suggest that intramolecular electron transfer occurs and that such an event causes additional photochemical mechanisms in chlorinated compounds where the fluorescence quantum yield is lower than in all other solvents and the values of the fluorescence decay change significantly. The dyes could be an interesting new class of fluorescence tags for labeling biomolecules and as dyes for organic photovoltaic materials.

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Section: Introductionmentioning

confidence: 99%

The photophysical characterisation of novel 3,9-dialkyloxy- and diacyloxyperylenes

et al. 2011

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“…[24] One of the most active areas of research involving PDI systems is related to their utilization in photoinduced electron-and/or energy-transfer processes. In this regard, electroactive units such as fluorenone and anthraquinone, [25] tetrathiafulvalene, [26] pyrene, [27] oligothiophene, [28] zinc phthalocyanine, [29] 3,4-ethylenedioxythiophene, [30] zinc porphyrin, [31] hexaazatriphenylenes, [32] anthracene dendrimers, [33] perylenemonoimide, [34] tetraboron-dipyrrin, [35] and poly(fluorene-alt-phenylene) [36] were connected to the PDI dye to reach molecular ensembles in which an electron-and/or energy-transfer event occurs. In the search for such electronic interaction involving PDI, supramolecular architectures were also recently described involving an oligo(p-phenylenevinylene), [37] a Abstract in French: De nouveaux assemblages covalents fullerne C 60 -pØrylne-3,4:9,10-bis(dicarboximide) (C 60 -PDI) (1-4) ont ØtØ synthØtisØs et caractØrisØs.…”

Section: Introductionmentioning

confidence: 99%

Fullerene C₆₀–Perylene‐3,4:9,10‐bis(dicarboximide) Light‐Harvesting Dyads: Spacer‐Length and Bay‐Substituent Effects on Intramolecular Singlet and Triplet Energy Transfer

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Leroy‐Lhez

Anh

et al. 2008

Chemistry A European J

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Novel covalent fullerene C(60)-perylene-3,4:9,10-bis(dicarboximide) (C(60)-PDI) dyads (1-4) were synthesized and characterized. Their electrochemical and photophysical properties were investigated. Electrochemical studies show that the reduction potential of PDI can be tuned relative to C(60) by molecular engineering through altering the substituents on the PDI bay region. It was demonstrated using steady-state and time-resolved spectroscopy that a quantitative, photoinduced energy transfer takes place from the PDI moiety, acting as a light-harvesting antenna, to the C(60) unit, playing the role of energy acceptor. The bay-substitution (tetrachloro [1 and 2] or tetra-tert-butylphenoxy [3 and 4]) of the PDI antenna and the linkage length (C(2) [1 and 3] or C(5) [2 and 4]) to the C(60) acceptor are important parameters in the kinetics of energy transfer. Femtosecond transient absorption spectroscopy indicates singlet-singlet energy-transfer times (from the PDI to the C(60) unit) of 0.4 and 5 ps (1), 4.5 and 27 ps (2), 0.8 and 12 ps (3), and 7 and 50 ps (4), these values being ascribed to two different conformers for each C(60)-PDI system. Subsequent triplet-triplet energy-transfer times (from the C(60) unit to the PDI) are slower and in the order of 0.8 ns (1), 6.2 ns (2), 2.7 ns (3), and 9 ns (4). Nanosecond transient absorption spectroscopy of final PDI triplet states show a marked influence of the bay substitution (tetrachloro- or tetra-tert-butylphenoxy), and triplet-state lifetimes (10-20 micros) and the PDI triplet quantum yields (0.75-0.52) were estimated. The spectroscopy showed no substantial solvent effect upon comparing toluene (non-polar) to benzonitrile (polar), indicating that no electron transfer is occurring in these systems.

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“…1), which exhibited light-harvesting functionalities from peripheral anthracene groups to the perylene cores. 5,6 During the course of our studies we found that energy transfer efficiencies were unaffected by relative orientation of the donor and acceptor chromophores within the dendrimer domains. In the present publication, we describe the results of continuing investigations, which delineate the mechanism of energy transfer in the multichromophore systems.…”

Section: Introductionmentioning

confidence: 73%

Mechanistic investigation of energy transfer in perylene-cored anthracene dendrimers

et al. 2008

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In this publication, we describe results of investigations focusing on detailed mechanisms of directed energy transfer in perylene-cored anthracene dendrimers. To obtain definitive statistical data for probing the energy transfer pathways, we synthesized four analogous dendrimers, which were designed to funnel the energy only from remote anthracene groups to the perylene cores. Static fluorescence studies with these dendrimers revealed that excitation of the anthracene groups led to the core emissions, indicating efficient energy transfer should be involved. Inspection of the energy transfer efficiencies obtained from all ten dendrimers demonstrated that single-step energy transfer should represent a key mechanism for the long-range energy transport in these dendrimers.

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Evaluation of energy transfer in perylene-cored anthracene dendrimers

Abstract: Quantitative evaluation of Förster-type fluorescence resonance energy transfer (FRET) was undertaken by statistical investigations on perylene-cored anthracene dendrimers.

Cited by 30 publications

References 14 publications

The photophysical characterisation of novel 3,9-dialkyloxy- and diacyloxyperylenes

The photophysical characterisation of novel 3,9-dialkyloxy- and diacyloxyperylenes

Fullerene C₆₀–Perylene‐3,4:9,10‐bis(dicarboximide) Light‐Harvesting Dyads: Spacer‐Length and Bay‐Substituent Effects on Intramolecular Singlet and Triplet Energy Transfer

Mechanistic investigation of energy transfer in perylene-cored anthracene dendrimers

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Evaluation of energy transfer in perylene-cored anthracene dendrimers

Abstract: Quantitative evaluation of Förster-type fluorescence resonance energy transfer (FRET) was undertaken by statistical investigations on perylene-cored anthracene dendrimers.

Cited by 30 publications

References 14 publications

The photophysical characterisation of novel 3,9-dialkyloxy- and diacyloxyperylenes

The photophysical characterisation of novel 3,9-dialkyloxy- and diacyloxyperylenes

Fullerene C60–Perylene‐3,4:9,10‐bis(dicarboximide) Light‐Harvesting Dyads: Spacer‐Length and Bay‐Substituent Effects on Intramolecular Singlet and Triplet Energy Transfer

Mechanistic investigation of energy transfer in perylene-cored anthracene dendrimers

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Fullerene C₆₀–Perylene‐3,4:9,10‐bis(dicarboximide) Light‐Harvesting Dyads: Spacer‐Length and Bay‐Substituent Effects on Intramolecular Singlet and Triplet Energy Transfer