Cascades of energy and electron transfer in a panchromatic absorber

Joseph, Jan; Bauroth, Stefan; Charisiadis, Asterios; Charalambidis, Georgios; Coutsolelos, Athanassios G.; Guldi, Dirk M.

doi:10.1039/d2nr02404g

Cited by 5 publications

(4 citation statements)

References 37 publications

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“…[23,24] To do this, a number of non-covalently supramolecular systems were created and synthesized using various binding mechanisms in order to mimic biological systems' operations and comprehend the fundamental ideas behind photoinduced energy-transfer and electron-transfer reactions in the photosynthetic systems' reaction centers. [25][26][27][28][29][30][31][32][33][34][35][36] Compared to covalent systems, such noncovalently connected donor-acceptor complexes have the benefit of being simpler to assemble.…”

Section: Introductionmentioning

confidence: 99%

“…The photo‐ and redox‐active elements in the bacterial photosynthetic reaction centers are grouped into a protein matrix in a well‐organized manner through non‐covalent interactions, as was previously shown [23,24] . To do this, a number of non‐covalently supramolecular systems were created and synthesized using various binding mechanisms in order to mimic biological systems’ operations and comprehend the fundamental ideas behind photoinduced energy‐transfer and electron‐transfer reactions in the photosynthetic systems’ reaction centers [25–36] . Compared to covalent systems, such non‐covalently connected donor‐acceptor complexes have the benefit of being simpler to assemble.…”

Section: Introductionmentioning

confidence: 99%

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Efficient Intra‐Supramolecular Electron Transfer in Zinc Porphyrin‐Coumarin Dyads

Eldeeb,

Mousa,

El‐Mashtoly

et al. 2024

ChemistrySelect

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We report herein the electron transfer process of a novel supramolecular dyads composed of zinc tetraphenylporphyrin (ZnTPP) and zinc 5,15‐dinonyl‐10,20‐diphenylporphyrin (ZnDPP), as electron donors, and ethyl(4‐pyridyl) coumarin‐3‐carboxylate (EPCC), as an electron acceptor, through metal‐ligand coordination bond in dichloromethane. The optical absorption studies revealed the formation of the moderate stable supramolecular donor‐acceptor dyads. The fluorescence measurements showed a significant fluorescence quenching of the singlet‐excited state of the singlet‐excited states of ZnTPP and ZnDPP upon addition of different amounts of EPCC. Such quenching behavior could be attributed to the electron transfer from the singlet‐excited state of porphyrin to EPCC. The bimolecular quenching rates were determined to be 1.98×1012 and 7.59×1012 L mol−1 s−1 for ZnTPP‐EPCC and ZnDPP‐EPCC, respectively, respectively. The fluorescence lifetime measurements suggest fast and efficient intra‐supramolecular electron transfer from the singlet states of porphyrin derivatives to EPCC. Furthermore, the formation of the supramolecular dyads was confirmed by the Raman technique and computational studies. The finding that the examined zinc porphyrin ‐ coumarin supramolecular dyads absorb light in a wide range of UV‐visible spectrum, fast and efficient electron transfer render the examined supramolecular dyad as simple models for the reaction centers of the artificial photosynthetic systems.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Efficient Intra‐Supramolecular Electron Transfer in Zinc Porphyrin‐Coumarin Dyads

Eldeeb,

Mousa,

El‐Mashtoly

et al. 2024

ChemistrySelect

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“…To overcome these shortcomings, connecting multi-chromophores with an electron spin convertor is a good strategy to construct heavy atom free PSs [8]. Benefiting from the high ISC efficiency, unique properties in biological systems and easy functionalization, fullerenes (mainly C 60 ) are frequently employed as efficient spin convertors [7,[19][20][21][22]. Significantly greater photosensitization efficiency has been achieved in C 60 -based triplet PSs.…”

Section: Introductionmentioning

confidence: 99%

Panchromatic Light-Absorbing [70]Fullerene-Perylene-BODIPY Triad with Cascade of Energy Transfer as an Efficient Singlet Oxygen Sensitizer

Dou

Dong

et al. 2023

Molecules

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A panchromatic light-absorbing [70]fullerene-perylene-BODIPY triad (C70-P-B) was synthesized and applied as a heavy atom-free organic triplet photosensitizer for photooxidation. The photophysical processes were comprehensively investigated by the methods of steady-state spectroscopy, time-resolved spectroscopy, as well as theoretical calculations. C70-P-B shows a strong absorption ability from 300–620 nm. Efficient cascading intramolecular singlet-singlet energy transfer in C70-P-B was confirmed by the luminescence study. The backward triplet excited state energy transfer from C70 moiety to perylene then occurs to populate 3perylene*. Thus, the triplet excited states of C70-P-B are distributed on both C70 and perylene moiety with lifetimes of 23 ± 1 μs and 175 ± 17 μs, respectively. C70-P-B exhibits excellent photooxidation capacity, and its yield of singlet oxygen reaches 0.82. The photooxidation rate constant of C70-P-B is 3.70 times that of C70-Boc and 1.58 times that of MB, respectively. The results in this paper are useful for designing efficient heavy atom-free organic triplet photosensitizers for practical application in photovoltaics, photodynamic therapy, etc.

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“…One step further, significant efforts have been made in developing multi‐chromophore systems able to efficiently harvest light across the entire visible range [5a–c] . To this end, electron accepting fullerenes are replaced by porphyrinoids.…”

Section: Introductionmentioning

confidence: 99%

A Novel Electron Donor‐Acceptor Carbazole‐Zn(II)Phthalocyanine – Perfluorinated Subphthalocyanine Conjugate: Synthesis, Characterization, and Photoinduced Electron‐Transfer

et al. 2022

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Porphyrinoids are considered perfect candidates for the preparation of model electron donor-acceptor (D-A) systems as they enable fast and efficient photoinduced electron transfer. Herein, we report on the synthesis and photophysical characterization of a ZnPcÀ SubPc conjugate covalently connected through a short-range alkyne spacer. We designed and prepared the conjugate, which comprise, on the one hand, a perfluorinated SubPc with strong electron acceptor character and, on the other, a Pc peripherally functionalized with carbazoles with strong electron donor character. Photoinduced electron transfer events are in-depth analyzed by several techniques, including steady-state absorption, time-resolved emission and transient absorption measurements on different time scales. Our studies confirm a full charge separation occurring from a photoexcited charge transfer state.

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Cascades of energy and electron transfer in a panchromatic absorber

Abstract: The investigation of molecular model systems is fundamental towards a deeper understanding of key photochemical steps in natural photosynthesis. In here, we report an entirely non-covalent triad consisting of boron...

Cited by 5 publications

References 37 publications

Efficient Intra‐Supramolecular Electron Transfer in Zinc Porphyrin‐Coumarin Dyads

Efficient Intra‐Supramolecular Electron Transfer in Zinc Porphyrin‐Coumarin Dyads

Panchromatic Light-Absorbing [70]Fullerene-Perylene-BODIPY Triad with Cascade of Energy Transfer as an Efficient Singlet Oxygen Sensitizer

A Novel Electron Donor‐Acceptor Carbazole‐Zn(II)Phthalocyanine – Perfluorinated Subphthalocyanine Conjugate: Synthesis, Characterization, and Photoinduced Electron‐Transfer

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