Charge Separation Dynamics and Opto‐Electronic Properties of a Diaminoterephthalate‐C<sub>60</sub> Dyad

Pittalis, Stefano; Delgado, Alain; Robin, Jörg; Freimuth, Lena; Christoffers, Jens; Lienau, Christoph; Rozzi, Carlo Andrea

doi:10.1002/adfm.201402316

Cited by 21 publications

(27 citation statements)

References 38 publications

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“…Although the starting material 33 shows the normal fluorescence behavior, the emission is quenched by the C 60 unit in compound 34 ( Φ = 3 % to Φ = 0.1 %). Pittalis et al studied the opto‐electronic properties of the dyad 34 by time‐dependent DFT calculations and determined the charge separation rate . Simulations of the coupled electronic and nuclear dynamics of the excited state in the Ehrenfest approximation were carried out on a sub 100 fs time scale in order to gain insights into the mechanisms driving the charge separation.…”

Section: Monofunctionalized Dyesmentioning

confidence: 99%

Diaminoterephthalate Fluorescence Dyes – Versatile Tools for Life Sciences and Materials Science

Christoffers

2018

Eur J Org Chem

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The 2,5‐diaminoterephthalate (DAT) structural motif is a powerful chromophore with remarkable fluorescence properties. Containing two carboxylate and two amino groups, it defines a colored molecular scaffold that allows for orthogonal functionalization with up to four different functional units. These compounds can be accessed in a remarkably simple fashion through reactions of succinyl succinates with amines, followed by aerobic oxidation, which is, from a preparative point of view, an issue of paramount importance. Even though DATs have been known since the beginning of the last century, compared to other classes of dyes they are so far underrated in the literature. This review highlights applications in life sciences and materials science. Equipped with maleimides and cyclooctyne moieties, for example, the chromophore can be covalently conjugated to biomolecules, which allows for the study of protein conformations and protein–protein interactions. In some cases, DATs serve as “turn‐on” probes, because their fluorescence quantum yields are increased by orders of magnitude upon reaction with the molecular target. Additionally, DAT fluorophores exhibit efficient emission in the solid state. By choosing appropriate substituents at the amino and carboxylate moieties, the emission wavelengths can be tuned in a broad range. As nanocrystalline needles, for example, DATs can be applied as fluorescence antennas for plasmon polaritons on a gold surface.

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Section: Monofunctionalized Dyesmentioning

confidence: 99%

Diaminoterephthalate Fluorescence Dyes – Versatile Tools for Life Sciences and Materials Science

Christoffers

2018

Eur J Org Chem

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“…In an Ehrenfest approach the electrons are described on the level of TDDFT and the nuclei are subject to classical equations of motion due to the forces exerted by the electron distribution. Despite the success of this molecular dynamics approach [49] for predicting vibrationally-assisted charge-transfer processes [50] in photovaltic molecules, the Born-Oppenheimer (BO) approximation is an inherent limitation hereby. For excited-state properties, where the nuclear and electronic dynamics are strongly mixed, BO-type molecular dynamics is not predictive.…”

Section: Simulationsmentioning

confidence: 99%

Femtosecond dynamics of correlated many-body states in C₆₀ fullerenes

Usenko

Schüler

Azima

et al. 2017

J. Phys.: Conf. Ser.

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Fullerene complexes may play a key role in the design of future molecular electronics and nanostructured devices with potential applications in light harvesting using organic solar cells. Charge and energy flow in these systems is mediated by many-body effects. We studied the structure and dynamics of laser-induced multielectron excitations in isolated C 60 by two-photon photoionization as a function of excitation wavelength using a tunable fs UV laser and developed a corresponding theoretical framework on the basis of ab initio calculations. The measured resonance line width gives direct information on the excited state lifetime. From the spectral deconvolution we derive a lower limit for purely electronic relaxation on the order of τ el = 10 +5 −3 fs. Energy dissipation towards nuclear degrees of freedom is studied in time-resolved techniques. The evaluation of the non-linear autocorrelation trace gives a characteristic time constant of τ vib = 400 ± 100 fs for the exponential decay. In line with the experiment, the observed transient dynamics is explained theoretically by nonadiabatic (vibronic) couplings involving the correlated electronic, the nuclear degrees of freedom (accounting for the Herzberg-Teller coupling), and their interplay.

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“…In an Ehrenfest approach the electrons are described on the level of TDDFT and the nuclei are subject to classical equations of motion due to the forces exerted by the electron distribution. Despite the success of this molecular dynamics approach [49] for predicting vibrationally-assisted charge-transfer processes [50] in photovoltaics the Born-Oppenheimer (BO) approximation is an inherent limitation. For excited-state properties, where the nuclear and electronic dynamics are strongly mixed, BO-type molecular dynamics is not predictive.…”

Section: Simulationsmentioning

confidence: 99%

Femtosecond dynamics of correlated many-body states in C₆₀fullerenes

et al. 2016

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Fullerene complexes may play a key role in the design of future molecular electronics and nanostructured devices with potential applications in light harvesting using organic solar cells. Charge and energy flow in these systems is mediated by many-body effects. We studied the structure and dynamics of laser-induced multi-electron excitations in isolated C 60 by two-photon photoionization as a function of excitation wavelength using a tunable fs UV laser and developed a corresponding theoretical framework on the basis of ab initio calculations. The measured resonance line width gives direct information on the excited state lifetime. From the spectral deconvolution we derive a lower limit for purely electronic relaxation on the order of t = -+ 10 el 3 5 fs. Energy dissipation towards nuclear degrees of freedom is studied with time-resolved techniques. The evaluation of the nonlinear autocorrelation trace gives a characteristic time constant of t =  400 100 vib fs for the exponential decay. In line with the experiment, the observed transient dynamics is explained theoretically by nonadiabatic (vibronic) couplings involving the correlated electronic, the nuclear degrees of freedom (accounting for the Herzberg-Teller coupling), and their interplay.

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Charge Separation Dynamics and Opto‐Electronic Properties of a Diaminoterephthalate‐C₆₀ Dyad

Cited by 21 publications

References 38 publications

Diaminoterephthalate Fluorescence Dyes – Versatile Tools for Life Sciences and Materials Science

Diaminoterephthalate Fluorescence Dyes – Versatile Tools for Life Sciences and Materials Science

Femtosecond dynamics of correlated many-body states in C₆₀ fullerenes

Femtosecond dynamics of correlated many-body states in C₆₀fullerenes

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Charge Separation Dynamics and Opto‐Electronic Properties of a Diaminoterephthalate‐C60 Dyad

Cited by 21 publications

References 38 publications

Diaminoterephthalate Fluorescence Dyes – Versatile Tools for Life Sciences and Materials Science

Diaminoterephthalate Fluorescence Dyes – Versatile Tools for Life Sciences and Materials Science

Femtosecond dynamics of correlated many-body states in C60 fullerenes

Femtosecond dynamics of correlated many-body states in C60fullerenes

Contact Info

Product

Resources

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Charge Separation Dynamics and Opto‐Electronic Properties of a Diaminoterephthalate‐C₆₀ Dyad

Femtosecond dynamics of correlated many-body states in C₆₀ fullerenes

Femtosecond dynamics of correlated many-body states in C₆₀fullerenes