Kontrolle des intramolekularen Förster‐Resonanzenergietransfers und der Singulettspaltung in einem Subporphyrazin‐Pentacen‐Konjugat mittels Lösungsmittelpolarität

Guzmán, David; Papadopoulos, Ilias; Lavarda, Giulia; Rami, Parisa R.; Tykwinski, Rik R.; Rodríguez‐Morgade, M. Salomé; Guldi, Dirk M.; Torres, Tomás

doi:10.1002/ange.202011197

Cited by 3 publications

(5 citation statements)

References 48 publications

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“…A three species kinetic model to fit the raw data for Pnc 2 COOH is well established and also applied in this work (Figures S14, S15, S20, and S21, Supporting Information). [11][12][13][14] The maxima of the first singlet excited state 1 (S 1 S 0 ) Pnc2 are found in the visible range at 451 and 510 nm and at 1386 nm in the near-infrared (NIR), along with a shoulder at 570 nm. Groundstate bleaching (GSB) covers a wavelength range from ≈600 to 670 nm.…”

Section: Resultsmentioning

confidence: 99%

“…A comparison of A, that is, BODIPYPnc 2 , with similar systems including subporphyrazine conjugates and subphthalocyanine-pentacene conjugates, with rates of k FRET = 1.14 and 4.09 × 10 11 s −1 , respectively, in benzonitrile, demonstrates that A exhibits a similar or even more efficient FRET. [11,14,20]…”

Section: Resultsmentioning

confidence: 99%

“…[6] Various porphyrinoids have been investigated as energy-donor antennas to widen the spectral range for activation of SF. [11][12][13][14] Nevertheless, these chromophores feature drawbacks that relate to their limited photo-stability and versatility toward chemical modification. [15] Boron-dipyrromethene (BODIPY) is a versatile molecular building block that has not yet been exploited to enable SF.…”

Section: Introductionmentioning

confidence: 99%

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Förster Resonance Energy Transfer Sensitized Singlet Fission in BODIPY‐Pentacene Dimer Conjugates

Wollny

Lavarda

Papadopoulos

et al. 2023

Advanced Optical Materials

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In the present work, the energy donor 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) is used for the first time in combination with a pentacene dimer (Pnc2) to provide the conjugate BODIPYPnc2 that features absorption throughout a large part of the solar spectrum. Upon photoexcitation, the singlet excited state energy of BODIPY is transferred to the pentacene dimer via intramolecular Förster resonance energy transfer (FRET). Subsequently, the pentacene dimer undergoes intramolecular singlet fission. In this process, a singlet correlated triplet pair is generated from the first singlet excited state via coupling to an intermediate state. The results show that solvent polarity has an influence on the system, with the largest FRET rate (i.e., 7.46 × 1011 s−1) being obtained in the most polar solvent (namely, benzonitrile) along with the largest triplet quantum yield (i.e., 207 ± 20%).

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Förster Resonance Energy Transfer Sensitized Singlet Fission in BODIPY‐Pentacene Dimer Conjugates

Wollny

Lavarda

Papadopoulos

et al. 2023

Advanced Optical Materials

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“…Thus, peripheral substitution constitutes a powerful tool to tune absorption, luminescent and redox profiles of SubPzs using heteroatoms, [1a,7] aryl, [3,6] or vinyl groups, [6a] allowing to design chromophores with tailored properties, like red absorbers [6a] and non-fullerene electronacceptors. [6b] As a direct application of this nascent SubPz chemistry, SubPz-based supramolecular devices for singlet fission, [8] and green-to-NIR photochromic switches, [9] have been recently reported.…”

Section: Introductionmentioning

confidence: 99%

“…[14] Chlorinated subporphyrazines (ClSubPz) early showed a higher tendency to hydrolyze in the presence of water than the corresponding SubPc relatives, suggesting a greater axial reactivity of SubPzs. [1a] However, axial functionalization of the pyrrolic series has been limited so far to the substitution of the original chlorine atom by hydroxy, [1] aryloxy [8,15] or fluorine groups. [15a] Axial functionalization usually does not alter the absorption profile of SubPzs.…”

Section: Introductionmentioning

confidence: 99%

Tuning Fluorescence and Singlet Oxygen Quantum Yields of Subporphyrazines by Axial Functionalization

Ben Ahmed,

Pérez de Bustos,

Pina

et al. 2024

ChemPlusChem

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The axial functionalization of Subporphyrazines (SubPzs) with unreported alkoxy groups, carboxy and carboperoxy rests, as well as sulfanyl, aryl and amino groups, forming B−O, B−S, B−C, and B−N bonds, respectively, has been investigated. The studied oxygen nucleophiles include aromatic and sterically demanding aliphatic alcohols, along with carboxylic acids and peracids. In general, direct substitution of the chloro‐SubPz by oxygen nucleophiles of diverse nature proceeds smoothly, with yields of the isolated alkoxy and carboxy‐substituted SubPzs ranging from 49 to 100 %. Conversely, direct substitution with sulphur, carbon and nitrogen nucleophiles do not afford the corresponding substituted SubPzs. In these cases, a stepwise procedure involving an axial triflate‐SubPz intermediate was employed, affording only the phenyl‐SubPz in 8 % yield. The major compound under these conditions was the unreported SubPz μ‐oxo dimer, presumably arising from substitution of the triflate‐SubPz by the in situ generated hydroxy‐SubPz. This result indicates a quite low reactivity of the TfO‐SubPz intermediate with carbon, sulphur and nitrogen nucleophiles. All SubPzs prepared in this work exhibited fluorescence at 510–515 nm with quantum yields ranging from 0.1 to 0.24. Additionally, all SubPzs generated singlet oxygen, with ΦΔ values ranging from 0.15 to 0.57, which show no apparent correlation with the axial substituents.

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Exploring the Association of Electron‐Donating Corroles with Phthalocyanines as Electron Acceptors

Platzer

Berna

Bischetti

et al. 2022

Chemistry A European J

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Electron‐donating corroles (Cor) were integrated with electron‐accepting phthalocyanines (Pc) to afford two different non‐covalent Cor ⋅ Pc systems. At the forefront was the coordination between a 10‐meso‐pyridine Cor and a ZnPc. The complexation was corroborated in a combination of NMR, absorption, and fluorescence assays, and revealed association with binding constants as high as 106 m−1. Steady‐state and time‐resolved spectroscopies evidenced that regardless of exciting Cor or Pc, the charge‐separated state evolved efficiently in both cases, followed by a slow charge‐recombination to reinstate the ground state. The introduction of non‐covalent linkages between Cor and Pc induces sizeable differences in the context of light harvesting and transfer of charges when compared with covalently linked Cor‐Pc conjugates.

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Kontrolle des intramolekularen Förster‐Resonanzenergietransfers und der Singulettspaltung in einem Subporphyrazin‐Pentacen‐Konjugat mittels Lösungsmittelpolarität

Cited by 3 publications

References 48 publications

Förster Resonance Energy Transfer Sensitized Singlet Fission in BODIPY‐Pentacene Dimer Conjugates

Förster Resonance Energy Transfer Sensitized Singlet Fission in BODIPY‐Pentacene Dimer Conjugates

Tuning Fluorescence and Singlet Oxygen Quantum Yields of Subporphyrazines by Axial Functionalization

Exploring the Association of Electron‐Donating Corroles with Phthalocyanines as Electron Acceptors

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