Novel BODIPY-C60 derivatives with tuned photophysical and electron-acceptor properties: Isoxazolino[60]fullerene and pyrrolidino[60]fullerene

Cabrera-Espinoza, Andrea; Insuasty, Braulio; Ortíz, Alejandro

doi:10.1016/j.jlumin.2017.09.043

Cited by 20 publications

(25 citation statements)

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“…20,23 Regarding the chromophores used both as light-harvester and electron donor, 4,4'-Difluoro-4-bora-3a,4a-diaza-s-indacenes (referred to as BODIPYs) have recently gained more attention in the design of donor-C60 conjugates. [24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39] Indeed, BODIPYs (BDPs) are chemically stable and display remarkable photophysical properties, including high absorption coefficients and emission quantum yields. Another remarkable feature relies on the ease of functionalization of the BDP core, allowing to tune its spectral and electrochemical properties.…”

Section: Introductionmentioning

confidence: 99%

“…Another important feature relies on the ease of functionalization of the BODIPY core, allowing to tune its spectral and electrochemical properties. (41) In many examples, it has been shown that the PET in these BODIPY-C60 assemblies was the main pathway leading to charge-separated states, (26,27,29,(31)(32)(33)(34)(35)(36)(37)39) whereas energy transfer appeared as a competitive process in a few cases. (25,28) The occurrence of this PET in these BODIPY-fullerene systems observed in solution could also be exploited in the construction of photocurrent-generating photoelectrochemical cells.…”

Section: Introductionmentioning

confidence: 99%

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Photoinduced Electron Transfer and Energy Transfer Processes in a Flexible BODIPY-C₆₀ Dyad

et al. 2020

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A new donor–acceptor dyad composed of a BODIPY (4,4′-difluoro-4-bora-3a,4a-diaza-s-indacene) donor and a fullerene C60 acceptor has been synthesized and characterized. This derivative has been prepared using a clickable fullerene building block that bears an alkyne moiety and a maleimide unit. The post-functionalization of the maleimide group by a BODIPY thiol leads to a BODIPY-C60 dyad, leaving the alkyne moiety for further functional arrangement. On the basis of the combination of semi-empirical and density functional theory (DFT) calculations, spectroelectrochemical experiments, and steady-state and time-resolved spectroscopies, the photophysical properties of this new BODIPY-C60 dyad were thoroughly studied. By using semi-empirical calculations, the equilibrium of three conformations of the BODIPY-C60 dyad has been deduced, and their molecular orbital structures have been analyzed using DFT calculations. Two short fluorescence lifetimes were attributed to two extended conformers displaying variable donor–acceptor distances (17.5 and 20.0 Å). Additionally, the driving force for photoinduced electron transfer from the singlet excited state of BODIPY to the C60 moiety was calculated using redox potentials determined with electrochemical studies. Spectroelectrochemical measurements were also carried out to investigate the absorption profiles of radicals in the BODIPY-C60 dyad in order to assign the transient species in pump–probe experiments. Under selective photoexcitation of the BODIPY moiety, occurrences of both energy and electron transfers were demonstrated for the dyad by femtosecond and nanosecond transient absorption spectroscopies. Photoinduced electron transfer occurs in the folded conformer, while energy transfer is observed in extended conformers.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Photoinduced Electron Transfer and Energy Transfer Processes in a Flexible BODIPY-C₆₀ Dyad

et al. 2020

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“…In the development of the criteria here described, we consider the molecular systems reported in 6,28,29 (see Figure 1). These exhibit experimental parameters already measured which allow for a direct comparison with our theoretical results, via the calculation of observables such as electronic energy levels, absorption spectra, charge transfer states, and others.…”

Section: A Molecular Systems and Computational Resultsmentioning

confidence: 99%

“…During the past two decades, organic solar cells have attracted much attention due to their quick improvement of photovoltaic properties and environmental and economic advantages; these include low-cost fabrication, lightweight, mechanical flexibility, high versatility due to applications in many fields, and the simplicity of the synthesis process [1][2][3] . The improvement of organic materials photo-physical capabilities of new hole transporting material (HTM) and electron transporting material (ETM), which constitute the photo-active components in organic photovoltaic (OPV) cell devices, can increase the performance of such solar energy conversion materials [4][5][6][7][8] . Thus, BODIPY-Fullerene derivatives synthesis becomes a valuable alternative to compose hole and electron transporting materials.…”

Section: Introductionmentioning

confidence: 99%

“…In this work, we propose novel molecular systems derived from BODIPY-fullerene (see Figure 1), which exhibit experimental evidence of intramolecular electron transfer processes as D-π-A materials 6,28,29 . By means of Scharber's model, we were able to compute the PCE, and to estimate the maximum conversion efficiency (under ideal conditions), thus, establishing some working conditions for application to photovoltaic devices.…”

Section: Introductionmentioning

confidence: 99%

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Photophysical Properties of BODIPY-derivatives for the Implementation of Organic Solar Cells: A Computational Approach

Madrid-Usuga,

Ortiz,

Reina

2021

Preprint

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Solar cells based on organic compounds are a proven emergent alternative to conventional electrical energy generation. Here, we provide a computational study of power conversion efficiency optimization of BODIPY-derivatives by means of their associated open circuit voltage, short-circuit density, and fill factor. In so doing, we compute for the derivatives' geometrical structures, energy levels of frontier molecular orbitals, absorption spectra, light collection efficiencies, and exciton binding energies, via density functional theory (DFT) and time dependent (TD)-DFT calculations. We fully-characterize four D-π-A (BODIPY) molecular systems of high efficiency and improved Jsc that are well suited for integration into bulk heterojunction (BHJ) organic solar cells as electron-donor materials in the active layer. Our results are two-fold: We found that molecular complexes with an structural isoxazoline ring exhibit a higher power conversion efficiency (PCE), a useful result for improving the BHJ current, and, on the other hand, by considering the molecular systems as electron-acceptor materials, with P3HT as the electron-donor in the active layer, we found a high PCE compound favorability with a pyrrolidine ring in its structure, in contrast to the molecular systems built with an isoxazoline ring. The theoretical characterization of the electronic properties of the BODIPY-derivatives here provided, computed with a combination of ab-initio methods and quantum models, can be readily applied to other sets of molecular complexes in order to hierarchize optimal power conversion efficiency.

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Photoinduced Electron Transfer in Clicked Ferrocene‐BODIPY‐Fullerene Conjugates

Allard

Rabah

Fatima

et al. 2023

Helvetica Chimica Acta

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Ferrocene‐BODIPY (Fc‐BDP) conjugates in which one or two ferrocene entities are linked to the β‐positions of the BODIPY core by an ethynyl bridge have been developed. These derivatives were easily and efficiently grafted onto a dual‐clickable fullerene platform using CuAAC reactions, leading to a clickable Fc‐BDP‐C60 triad and a clickable [Fc]2‐BDP‐C60 tetrad which can be used for further derivatization with complex structures. Due to the extended π‐conjugation and the presence of an intramolecular charge transfer band from Fc to BDP, all these conjugates display a broad absorption in the visible region, which is bathochromically shifted when two Fc are appended to the BDP core. Ultrafast multistep electron transfers leading to charge stabilization were demonstrated in the Fc‐BDP‐C60 triad and [Fc]2‐BDP‐C60 tetrad by femtosecond transient absorption studies.

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Novel BODIPY-C60 derivatives with tuned photophysical and electron-acceptor properties: Isoxazolino[60]fullerene and pyrrolidino[60]fullerene

Cited by 20 publications

References 32 publications

Photoinduced Electron Transfer and Energy Transfer Processes in a Flexible BODIPY-C₆₀ Dyad

Photoinduced Electron Transfer and Energy Transfer Processes in a Flexible BODIPY-C₆₀ Dyad

Photophysical Properties of BODIPY-derivatives for the Implementation of Organic Solar Cells: A Computational Approach

Photoinduced Electron Transfer in Clicked Ferrocene‐BODIPY‐Fullerene Conjugates

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Novel BODIPY-C60 derivatives with tuned photophysical and electron-acceptor properties: Isoxazolino[60]fullerene and pyrrolidino[60]fullerene

Cited by 20 publications

References 32 publications

Photoinduced Electron Transfer and Energy Transfer Processes in a Flexible BODIPY-C60 Dyad

Photoinduced Electron Transfer and Energy Transfer Processes in a Flexible BODIPY-C60 Dyad

Photophysical Properties of BODIPY-derivatives for the Implementation of Organic Solar Cells: A Computational Approach

Photoinduced Electron Transfer in Clicked Ferrocene‐BODIPY‐Fullerene Conjugates

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Photoinduced Electron Transfer and Energy Transfer Processes in a Flexible BODIPY-C₆₀ Dyad

Photoinduced Electron Transfer and Energy Transfer Processes in a Flexible BODIPY-C₆₀ Dyad