Two-photon absorption of perylene derivatives: Interpreting the spectral structure

Piovesan, Erick; Silva, D.L.; Boni, Leonardo De; Guimarães, Francisco Eduardo Gontijo; Misoguti, Lino; Zaleśny, Robert; Bartkowiak, Wojciech; Mendonça, Cleber Renato

doi:10.1016/j.cplett.2009.07.100

Cited by 14 publications

(10 citation statements)

References 44 publications

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“…two-photon lineshapes are completely different, indicating that the two different excitation modes access different states. A similar two-photon absorption line shape has been measured for PER, 46,47 and other workers have shown that PER derivatives have different one-and two-photon absorption spectra, 48,49 as expected for this class of highly symmetric molecules. In PP, the one-and two-photon spectra both exhibit similar vibronic progressions with spacings of ∼20 nm (corresponding to a 1000−1200 cm −1 vibrational mode characteristic of PAH's).…”

Section: ■ Experimental Sectionsupporting

confidence: 79%

Assessing the Potential of Peropyrene as a Singlet Fission Material: Photophysical Properties in Solution and the Solid State

et al. 2013

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The photophysical behavior of the polycyclic aromatic hydrocarbon peropyrene is studied both in dilute solution and in the solid state, with the goal of evaluating this molecule as a singlet fission (SF) material. In solution, the fluorescence quantum yield is consistently in the range 0.90−0.95, while the fluorescence lifetime changes from 3.2 to 5.5 ns. Analysis of the solvent dependence of the radiative rate provides evidence that the bright 1 B u singlet state mixes with a second, optically dark state. The presence of a dark state slightly above the 1 B u state in energy is confirmed using two-photon fluorescence excitation spectroscopy. The crystal structure of solid peropyrene consists of a herringbone arrangement of π-stacked molecular pairs, similar to the αpolymorph of perylene. There are two emitting species, centered at approximately 550 and 650 nm, both of which are formed within the 15 ps time resolution of the experiment, and which relax independently via biexponential decays. We find no evidence for rapid SF in the peropyrene crystals, most likely due to the large shift of the singlet state to lower energy where it no longer fulfills the energy condition for SF. These results demonstrate how both energetics and crystal packing influence the ability of a molecule to function as a SF material.

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Section: ■ Experimental Sectionsupporting

confidence: 79%

Assessing the Potential of Peropyrene as a Singlet Fission Material: Photophysical Properties in Solution and the Solid State

et al. 2013

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“…It should be noted that PBI works as an efficient 2PA unit, and the maximum 2PA wavelengths of these PBIs were similar to the 640 nm reported for the fluorenylperylene-functionalized diimides. 20,43 Among them, PCB-PBI has a high δ 2PA value of ∼1890 GM, implying that the extension of total ICT efficiency and effective conjugation size leads to an obvious increase of δ 2PA values (Table S5). For consistently comparing the component contribution in this series, the normalization criterion based on the number of PBI units was set to obtain a relevant figure of merit.…”

Section: ■ Introductionmentioning

confidence: 99%

Resonance-Enhanced Two-Photon Absorption and Optical Power Limiting Properties of Three-Dimensional Perylene Bisimide Derivatives

et al. 2021

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Push−pull organic structures characterized by an intramolecular charge transfer (ICT) process and π-electron delocalization are potentially interesting luminescent materials. A series of three-dimensional o-carborane-containing perylene bisimide derivatives (PBIs) were synthesized, and their optical properties were systematically investigated to illustrate the stereo effect, especially on the two-photon absorption (2PA) and optical power limiting (OPL) properties. Open-aperture Z-scan curves showed that all four PBIs displayed strong and broad two-photon absorptivities based on the resonance-enhanced phenomenon. The maximum degenerate two-photon absorption cross section (δ 2PA ) increased with the number of PBI substituents. The derivative CB-PBI possessed a δ 2PA value of ∼2400 GM at 650 nm, a significant enhancement in comparison with that of the parent PBI (∼719 GM), ascribed to the present stereo effect. When the aromatic-donating units changed from naphthyl and pyrenyl to PBI, the generated multidimensional intramolecular charge transfer (ICT) from the aromatic units to the o-carborane cage contributed to the 2PA processes. All of the fluorophores exhibited excellent optical power limiting (OPL) performances as well as a minimum limiting threshold of ∼4.98 mJ/cm 2 for CB-PBI. These significant results not only allow us to get deep insight into the nature of the fundamental stereo effect and nonlinear optical (NLO) response involved but also guide us toward the design of new multifunctional luminescent materials.

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“…This includes branched chromophore, prion peptide nanostructures, porphyrin macrocycles, and cyclothiophenes . Among the different macromolecules investigated for enhanced NLO and TPA properties, both perylene bisimides and thiophene dendrimers have gained intense interest for their promising potential in organic electronic device application. , …”

Section: Introductionmentioning

confidence: 99%

“…19 Among the different macromolecules investigated for enhanced NLO and TPA properties, both perylene bisimides and thiophene dendrimers have gained intense interest for their promising potential in organic electronic device application. 20,21 Perylene bisimide dyes (PBIs) have been developed in the past few years and are now one of the most useful classes of fluorescence materials. 22 PBI dyes exhibit exceptional water solubility, thermal stability, fluorescence intensity, and photochemical stability with high fluorescence quantum yields up to 0.99.…”

Section: Introductionmentioning

confidence: 99%

Energy Migration in Dendritic Oligothiophene-Perylene Bisimides

Zhang

Bäuerle

2012

J. Phys. Chem. B

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A series of novel oligothiophene-perylene bisimide hybrid (DOTPBI) dendrimers up to the second generation (G0, G1, and G2) were investigated. Optical measurements such as nonlinear optical and time-resolved spectroscopy, including two-photon absorption, fluorescence upconversion, and excited state transient absorption were carried out. Results of these measurements revealed the ability of these molecules to undergo intramolecular fluorescence resonance energy transfer (FRET) from the dendritic oligothiophenes (DOT) to the perylene bismide (PBI) moiety. The delocalization length and the photoinduced electron transfer (PET) rate were investigated as a function of dendrimer generation. A fast energy transfer process from the DOT dendron to the PBI core was observed. For the case of the G2 dendrimer, with relatively large thiophene dendrons attached to the bay area of the perylene bisimide, the PBI core is highly twisted and its ability to self-assemble into π-π stacked aggregates is destroyed. As a result, among the three generations studied, G1, which has the best two-photon cross section and the most efficient energy transfer, is the best light harvesting material.

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Two-photon absorption of perylene derivatives: Interpreting the spectral structure

Cited by 14 publications

References 44 publications

Assessing the Potential of Peropyrene as a Singlet Fission Material: Photophysical Properties in Solution and the Solid State

Assessing the Potential of Peropyrene as a Singlet Fission Material: Photophysical Properties in Solution and the Solid State

Resonance-Enhanced Two-Photon Absorption and Optical Power Limiting Properties of Three-Dimensional Perylene Bisimide Derivatives

Energy Migration in Dendritic Oligothiophene-Perylene Bisimides

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