Perylene-3,4:9,10-bis(dicarboximide) linked to [60]fullerene as a light-harvesting antenna

Baffreau, Jérôme; Perrin, Lara; Leroy‐Lhez, Stéphanie; Hudhomme, Piétrick

doi:10.1016/j.tetlet.2005.04.132

Cited by 35 publications

(30 citation statements)

References 18 publications

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“…Nevertheless, by subtracting the contribution of PDI from the emission spectrum of 3 or 4, the fullerene emission is still observed, even when the PDI is selectively excited at wavelengths above 550 nm. [40] This result associated with the strong fluorescence quenching of PDI emission corroborates the hypothesis of an energy transfer from PDI to C 60 for these dyads. Energy levels are still in agreement as the first excited state of 10 is lying at 2.11 eV, that is, 0.32 eV above the first excited state of compound 14 in toluene (Table 4).…”

Section: Resultssupporting

confidence: 83%

“…bis(ruthenium phthalocyanine) moiety, [38] or zeolite crystals. [39] In the last three years, and in parallel to our first investigation, [40] new electroactive PDIbased systems involving the attractive fullerene C 60 electron acceptor were considered and the synthesis of many C 60 -PDI dyad or triad systems have now been reported. [41] Nevertheless, the spectral and kinetic characterization of the photoinduced processes that are inherent to the combination of these electroactive units have received little attention.…”

Section: Introductionmentioning

confidence: 98%

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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

Baffreau

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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Section: Resultssupporting

confidence: 83%

Section: Introductionmentioning

confidence: 98%

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

Baffreau

Leroy‐Lhez

Anh

et al. 2008

Chemistry A European J

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“…[20] Such bay region substituted PBIs were recently connected to fullerene C 60 with the aim of increasing the absorption of the n-type material incorporated in bulk-heterojunction devices of organic solar cells. [21] These C 60 -PBI dyads have the potential to be used as photosensitizers in the development of a new field of applications. [22] In contrast to PBI analogues, perylene-3,4:9,10-tetracarboxylic bis(benzimidazole) (PTCBI) derivatives 2 have been less investigated.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Electrochemical and Optical Absorption Properties of New Perylene‐3,4:9,10‐bis(dicarboximide) and Perylene‐3,4:9,10‐bis(benzimidazole) Derivatives

Perrin

Hudhomme

2011

Eur J Org Chem

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A series of perylene‐3,4:9,10‐bis(dicarboximide) (PBI) and perylene‐3,4:9,10‐bis(benzimidazole) (PTCBI) derivatives that are di‐ or tetra‐substituted at the bay region by electron‐donating or electron‐withdrawing groups have been synthesized as soluble n‐type semiconductors. Optical absorption spectroscopy and electrochemical analysis show that the nature of substitution at the bay region plays a crucial role in the modulation of the electronic properties of these PBI and PTCBI derivatives. Examination of these optical and electrochemical data in the light of energy levels identified by theoretical studies allowed a relationship between the structure and the electronic properties to be established.

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“…The principle of associating a dye attached to the fullerene was proposed to reach C 60 -PBI or C 60 -PMI dyads as super-absorbing fullerenes (Fig. 11) [84][85][86][87]. Even if the PCE were low using this dyad as an acceptor, the role of the perylenebisimide (PBI) acting as a light-harvesting antenna was evidenced by an efficient intramolecular energy transfer occurring from PBI onto C 60 and the relationship between electrochemical properties of the dyad and the P3HT: C 60 -PBI blend efficiency was evidenced [88].…”

Section: -P5 Epj Photovoltaicsmentioning

confidence: 99%

An overview of molecular acceptors for organic solar cells

Hudhomme

2013

EPJ Photovolt.

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Organic solar cells (OSCs) have gained serious attention during the last decade and are now considered as one of the future photovoltaic technologies for low-cost power production. The first dream of attaining 10% of power coefficient efficiency has now become a reality thanks to the development of new materials and an impressive work achieved to understand, control and optimize structure and morphology of the device. But most of the effort devoted to the development of new materials concerned the optimization of the donor material, with less attention for acceptors which to date remain dominated by fullerenes and their derivatives. This short review presents the progress in the use of non-fullerene small molecules and fullerene-based acceptors with the aim of evaluating the challenge for the next generation of acceptors in organic photovoltaics.

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Perylene-3,4:9,10-bis(dicarboximide) linked to [60]fullerene as a light-harvesting antenna

Cited by 35 publications

References 18 publications

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

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

Synthesis, Electrochemical and Optical Absorption Properties of New Perylene‐3,4:9,10‐bis(dicarboximide) and Perylene‐3,4:9,10‐bis(benzimidazole) Derivatives

An overview of molecular acceptors for organic solar cells

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Perylene-3,4:9,10-bis(dicarboximide) linked to [60]fullerene as a light-harvesting antenna

Cited by 35 publications

References 18 publications

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

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

Synthesis, Electrochemical and Optical Absorption Properties of New Perylene‐3,4:9,10‐bis(dicarboximide) and Perylene‐3,4:9,10‐bis(benzimidazole) Derivatives

An overview of molecular acceptors for organic solar cells

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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

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