Synthesis of New Porphyrin–Fullerene Dyads Capable of Forming Charge‐Separated States on a Microsecond Lifetime Scale

Konev, Alexander S.; Khlebnikov, Alexander F.; Prolubnikov, Pavel I.; Mereshchenko, Andrey S.; Povolotskiy, Alexey V.; Levin, Oleg V.; Hirsch, Andreas

doi:10.1002/chem.201404435

Cited by 21 publications

(10 citation statements)

References 77 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The bithiophene bay‐bridged perylene bisimide (PBI) macrocycles of Nuckolls and co‐workers [10] display one great example for such a tailored D−A system. Also non‐cyclic covalent donor‐acceptor linkages [11a–c] of, for example, PBI‐oligothiophene dyads were described within the past two decades [12] . Installation of thiophene moieties in the PBI's bay position leads to a bathochromic shift of the absorption compared to the unsubstituted PBI as well as fluorescence quenching due to charge transfer (CT) processes [13] .…”

Section: Introductionmentioning

confidence: 99%

Macrocyclic Donor‐Acceptor Dyads Composed of Oligothiophene Half‐Cycles and Perylene Bisimides

Bold

Stolte

Shoyama

et al. 2022

Chemistry A European J

View full text Add to dashboard Cite

A series of donor‐acceptor (D−A) macrocyclic dyads consisting of an electron‐poor perylene bisimide (PBI) π‐scaffold bridged with electron‐rich α‐oligothiophenes bearing four, five, six and seven thiophene units between the two phenyl‐imide substituents has been synthesized and characterized by steady‐state UV/Vis absorption and fluorescence spectroscopy, cyclic and differential pulse voltammetry as well as transient absorption spectroscopy. Tying the oligothiophene strands in a conformationally fixed macrocyclic arrangement leads to a more rigid π‐scaffold with vibronic fine structure in the respective absorption spectra. Electrochemical analysis disclosed charged state properties in solution which are strongly dependent on the degree of rigidification within the individual macrocycle. Investigation of the excited state dynamics revealed an oligothiophene bridge size‐dependent fast charge transfer process for the macrocyclic dyads upon PBI subunit excitation.

show abstract

Section: Introductionmentioning

confidence: 99%

Macrocyclic Donor‐Acceptor Dyads Composed of Oligothiophene Half‐Cycles and Perylene Bisimides

Bold

Stolte

Shoyama

et al. 2022

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…Photoinduced charge transfer processes have attracted great interest because of their fundamental role in applications such as solar cells and artificial photosynthetic systems. − The efficient use of sunlight requires the photogeneration of suitably long-lived charge separated states that are capable of forming applicable photocurrent or driving the multielectron chemistry of fuel synthesis. − Inspired by the natural photosynthetic process, where cascades of short-range photoinduced energy transfer and multistep electron transfer occur, a large variety of supramolecular systems and arrays have been developed with various donors and acceptors to form a donor–acceptor (D–A) architecture. − …”

Section: Introductionmentioning

confidence: 99%

Effect of Triplet State on the Lifetime of Charge Separation in Ambipolar D-A₁-A₂ Organic Semiconductors

et al. 2016

View full text Add to dashboard Cite

An ambipolar organic semiconductor with styrene based triphenylamine derivative (MTPA) as an electron donor (D), triazine group (TRC) as an electron acceptor (A 1 ), and 9,10-anthraquinone (AEAQ) as a second electron acceptor (A 2 ) has shown an 8-fold increase in the lifetime of charge separation with a high performance as solar cell materials with respect to the D-A 1 architecture and demonstrated a general D-A 1 -A 2 architecture as a promising materials design strategy for photovoltaics. Here we synthesized and characterized two new D-A 1 -A 2 compounds with perylene bisimide derivatives (PDI and PBI) as A 2 using an integrated experimental and computational method to study and compare the kinetics of three MTPA-TRC-A 2 systems. A two-step sequential decay pathway was observed in both MTPA-TRC-PDI and MTPA-TRC-PBI but a direct decay pathway in MTPA-TRC-AEAQ. The charge separated state with a lifetime of 22 ns in the PDI system and 75 ns in the PBI system relaxes to the corresponding triplet state followed by the decay to ground state in 827 ns and 29.2 μs, respectively. Thus, a triplet state with a lower energy than the charge separated state shortens the lifetime of the charge separated state but increases the overall lifetime of excited states.

show abstract

“…The C 60 fullerene has often been chosen as an excellent electron-acceptor since it presents a triple-degenerated low-energy LUMO. This molecular structure is also capable of reversibly accepting up to six electrons and offers unusually low reorganization energy in charge transfer processes allowing ultra-fast charge separation processes and slow charge recombination 80,81 . Therefore, we expect that the merger between the C 60 and the BODIPY unit may exhibit acceptor properties being able to act as electron-acceptor materials in molecular photovoltaic devices.…”

Section: G Molecular Systems As Electron-acceptor Materialsmentioning

confidence: 99%

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

Madrid-Usuga,

Ortiz,

Reina

2021

Preprint

View full text Add to dashboard Cite

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.

show abstract

Synthesis of New Porphyrin–Fullerene Dyads Capable of Forming Charge‐Separated States on a Microsecond Lifetime Scale

Cited by 21 publications

References 77 publications

Macrocyclic Donor‐Acceptor Dyads Composed of Oligothiophene Half‐Cycles and Perylene Bisimides

Macrocyclic Donor‐Acceptor Dyads Composed of Oligothiophene Half‐Cycles and Perylene Bisimides

Effect of Triplet State on the Lifetime of Charge Separation in Ambipolar D-A₁-A₂ Organic Semiconductors

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

Contact Info

Product

Resources

About

Synthesis of New Porphyrin–Fullerene Dyads Capable of Forming Charge‐Separated States on a Microsecond Lifetime Scale

Cited by 21 publications

References 77 publications

Macrocyclic Donor‐Acceptor Dyads Composed of Oligothiophene Half‐Cycles and Perylene Bisimides

Macrocyclic Donor‐Acceptor Dyads Composed of Oligothiophene Half‐Cycles and Perylene Bisimides

Effect of Triplet State on the Lifetime of Charge Separation in Ambipolar D-A1-A2 Organic Semiconductors

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

Contact Info

Product

Resources

About

Effect of Triplet State on the Lifetime of Charge Separation in Ambipolar D-A₁-A₂ Organic Semiconductors