Long-lived charge carrier generation in ordered films of a covalent perylenediimide–diketopyrrolopyrrole–perylenediimide molecule
The photophysics of a covalently linked perylenediimide–diketopyrrolopyrrole–perylenediimide acceptor–donor–acceptor molecule (PDI–DPP–PDI, 1 ) were investigated and found to be markedly different in solution versus in unannealed and solvent annealed films. Photoexcitation of 1 in toluene results in...
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| Published in | Chemical science (Cambridge) Vol. 6; no. 1; pp. 402 - 411 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
England
Royal Society of Chemistry
01.01.2015
|
| Subjects | |
| Online Access | Get full text |
| ISSN | 2041-6520 2041-6539 |
| DOI | 10.1039/C4SC02551B |
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| Abstract | The photophysics of a covalently linked perylenediimide–diketopyrrolopyrrole–perylenediimide acceptor–donor–acceptor molecule (PDI–DPP–PDI,
1
) were investigated and found to be markedly different in solution
versus
in unannealed and solvent annealed films. Photoexcitation of
1
in toluene results in quantitative charge separation in
τ
= 3.1 ± 0.2 ps, with charge recombination in
τ
= 340 ± 10 ps, while in unannealed/disordered films of
1
, charge separation occurs in
τ
< 250 fs, while charge recombination displays a multiexponential decay in ∼6 ns. The absence of long-lived, charge separation in the disordered film suggests that few free charge carriers are generated. In contrast, upon CH
2
Cl
2
vapor annealing films of
1
, grazing-incidence X-ray scattering shows that the molecules form a more ordered structure. Photoexcitation of the ordered films results in initial formation of a spin-correlated radical ion pair (electron–hole pair) as indicated by magnetic field effects on the formation of free charge carriers which live for ∼4 μs. This result has significant implications for the design of organic solar cells based on covalent donor–acceptor systems and shows that long-lived, charge-separated states can be achieved by controlling intramolecular charge separation dynamics in well-ordered systems. |
|---|---|
| AbstractList | Self-ordering of covalent electron donor–acceptor building blocks in thin films upon solvent vapor annealing results in a 10
4
increase in photo-generated charge carrier lifetime.
The photophysics of a covalently linked perylenediimide–diketopyrrolopyrrole–perylenediimide acceptor–donor–acceptor molecule (PDI–DPP–PDI,
1
) were investigated and found to be markedly different in solution
versus
in unannealed and solvent annealed films. Photoexcitation of
1
in toluene results in quantitative charge separation in
τ
= 3.1 ± 0.2 ps, with charge recombination in
τ
= 340 ± 10 ps, while in unannealed/disordered films of
1
, charge separation occurs in
τ
< 250 fs, while charge recombination displays a multiexponential decay in ∼6 ns. The absence of long-lived, charge separation in the disordered film suggests that few free charge carriers are generated. In contrast, upon CH
2
Cl
2
vapor annealing films of
1
, grazing-incidence X-ray scattering shows that the molecules form a more ordered structure. Photoexcitation of the ordered films results in initial formation of a spin-correlated radical ion pair (electron–hole pair) as indicated by magnetic field effects on the formation of free charge carriers which live for ∼4 μs. This result has significant implications for the design of organic solar cells based on covalent donor–acceptor systems and shows that long-lived, charge-separated states can be achieved by controlling intramolecular charge separation dynamics in well-ordered systems. The photophysics of a covalently linked perylenediimide-diketopyrrolopyrrole-perylenediimide acceptor-donor-acceptor molecule (PDI-DPP-PDI, 1) were investigated and found to be markedly different in solution versus in unannealed and solvent annealed films. Photoexcitation of 1 in toluene results in quantitative charge separation in τ = 3.1 ± 0.2 ps, with charge recombination in τ = 340 ± 10 ps, while in unannealed/disordered films of 1, charge separation occurs in τ < 250 fs, while charge recombination displays a multiexponential decay in ∼6 ns. The absence of long-lived, charge separation in the disordered film suggests that few free charge carriers are generated. In contrast, upon CH2Cl2 vapor annealing films of 1, grazing-incidence X-ray scattering shows that the molecules form a more ordered structure. Photoexcitation of the ordered films results in initial formation of a spin-correlated radical ion pair (electron-hole pair) as indicated by magnetic field effects on the formation of free charge carriers which live for ∼4 μs. This result has significant implications for the design of organic solar cells based on covalent donor-acceptor systems and shows that long-lived, charge-separated states can be achieved by controlling intramolecular charge separation dynamics in well-ordered systems.The photophysics of a covalently linked perylenediimide-diketopyrrolopyrrole-perylenediimide acceptor-donor-acceptor molecule (PDI-DPP-PDI, 1) were investigated and found to be markedly different in solution versus in unannealed and solvent annealed films. Photoexcitation of 1 in toluene results in quantitative charge separation in τ = 3.1 ± 0.2 ps, with charge recombination in τ = 340 ± 10 ps, while in unannealed/disordered films of 1, charge separation occurs in τ < 250 fs, while charge recombination displays a multiexponential decay in ∼6 ns. The absence of long-lived, charge separation in the disordered film suggests that few free charge carriers are generated. In contrast, upon CH2Cl2 vapor annealing films of 1, grazing-incidence X-ray scattering shows that the molecules form a more ordered structure. Photoexcitation of the ordered films results in initial formation of a spin-correlated radical ion pair (electron-hole pair) as indicated by magnetic field effects on the formation of free charge carriers which live for ∼4 μs. This result has significant implications for the design of organic solar cells based on covalent donor-acceptor systems and shows that long-lived, charge-separated states can be achieved by controlling intramolecular charge separation dynamics in well-ordered systems. The photophysics of a covalently linked perylenediimide-diketopyrrolopyrrole-perylenediimide acceptor-donor-acceptor molecule (PDI-DPP-PDI, 1) were investigated and found to be markedly different in solution versusin unannealed and solvent annealed films. Photoexcitation of 1 in toluene results in quantitative charge separation in tau = 3.1 plus or minus 0.2 ps, with charge recombination in tau = 340 plus or minus 10 ps, while in unannealed/disordered films of 1, charge separation occurs in tau < 250 fs, while charge recombination displays a multiexponential decay in similar to 6 ns. The absence of long-lived, charge separation in the disordered film suggests that few free charge carriers are generated. In contrast, upon CH sub(2)Cl sub(2) vapor annealing films of 1, grazing-incidence X-ray scattering shows that the molecules form a more ordered structure. Photoexcitation of the ordered films results in initial formation of a spin-correlated radical ion pair (electron-hole pair) as indicated by magnetic field effects on the formation of free charge carriers which live for similar to 4 mu s. This result has significant implications for the design of organic solar cells based on covalent donor-acceptor systems and shows that long-lived, charge-separated states can be achieved by controlling intramolecular charge separation dynamics in well-ordered systems. The photophysics of a covalently linked perylenediimide–diketopyrrolopyrrole–perylenediimide acceptor–donor–acceptor molecule (PDI–DPP–PDI, 1) were investigated and found to be markedly different in solution versus in unannealed and solvent annealed films. Photoexcitation of 1 in toluene results in quantitative charge separation in τ = 3.1 ± 0.2 ps, with charge recombination in τ = 340 ± 10 ps, while in unannealed/disordered films of 1, charge separation occurs in τ < 250 fs, while charge recombination displays a multiexponential decay in ~6 ns. The absence of long-lived, charge separation in the disordered film suggests that few free charge carriers are generated. In contrast, upon CH₂Cl₂ vapor annealing films of 1, grazing-incidence X-ray scattering shows that the molecules form a more ordered structure. Photoexcitation of the ordered films results in initial formation of a spin-correlated radical ion pair (electron–hole pair) as indicated by magnetic field effects on the formation of free charge carriers which live for ~4 μs. This result has significant implications for the design of organic solar cells based on covalent donor–acceptor systems and shows that long-lived, charge-separated states can be achieved by controlling intramolecular charge separation dynamics in well-ordered systems. The photophysics of a covalently linked perylenediimide–diketopyrrolopyrrole–perylenediimide acceptor–donor–acceptor molecule (PDI–DPP–PDI, 1 ) were investigated and found to be markedly different in solution versus in unannealed and solvent annealed films. Photoexcitation of 1 in toluene results in quantitative charge separation in τ = 3.1 ± 0.2 ps, with charge recombination in τ = 340 ± 10 ps, while in unannealed/disordered films of 1 , charge separation occurs in τ < 250 fs, while charge recombination displays a multiexponential decay in ∼6 ns. The absence of long-lived, charge separation in the disordered film suggests that few free charge carriers are generated. In contrast, upon CH 2 Cl 2 vapor annealing films of 1 , grazing-incidence X-ray scattering shows that the molecules form a more ordered structure. Photoexcitation of the ordered films results in initial formation of a spin-correlated radical ion pair (electron–hole pair) as indicated by magnetic field effects on the formation of free charge carriers which live for ∼4 μs. This result has significant implications for the design of organic solar cells based on covalent donor–acceptor systems and shows that long-lived, charge-separated states can be achieved by controlling intramolecular charge separation dynamics in well-ordered systems. The photophysics of a covalently linked perylenediimide-diketopyrrolopyrrole-perylenediimide acceptor-donor-acceptor molecule (PDI-DPP-PDI, ) were investigated and found to be markedly different in solution in unannealed and solvent annealed films. Photoexcitation of in toluene results in quantitative charge separation in = 3.1 ± 0.2 ps, with charge recombination in = 340 ± 10 ps, while in unannealed/disordered films of , charge separation occurs in < 250 fs, while charge recombination displays a multiexponential decay in ∼6 ns. The absence of long-lived, charge separation in the disordered film suggests that few free charge carriers are generated. In contrast, upon CH Cl vapor annealing films of , grazing-incidence X-ray scattering shows that the molecules form a more ordered structure. Photoexcitation of the ordered films results in initial formation of a spin-correlated radical ion pair (electron-hole pair) as indicated by magnetic field effects on the formation of free charge carriers which live for ∼4 μs. This result has significant implications for the design of organic solar cells based on covalent donor-acceptor systems and shows that long-lived, charge-separated states can be achieved by controlling intramolecular charge separation dynamics in well-ordered systems. |
| Author | Wasielewski, Michael R. Hartnett, Patrick E. Margulies, Eric A. Dyar, Scott M. Marks, Tobin J. Shoer, Leah E. Eaton, Samuel W. Cook, Andrew W. |
| AuthorAffiliation | a Department of Chemistry and Argonne-Northwestern Solar Energy Research (ANSER) Center , Northwestern University , Evanston , Illinois 60208-3113 , USA . Email: m-wasielewski@northwestern.edu ; Email: t-marks@northwestern.edu ; Fax: +1-847-467-1425 ; Tel: +1-847-467-1423 |
| AuthorAffiliation_xml | – name: a Department of Chemistry and Argonne-Northwestern Solar Energy Research (ANSER) Center , Northwestern University , Evanston , Illinois 60208-3113 , USA . Email: m-wasielewski@northwestern.edu ; Email: t-marks@northwestern.edu ; Fax: +1-847-467-1425 ; Tel: +1-847-467-1423 |
| Author_xml | – sequence: 1 givenname: Patrick E. surname: Hartnett fullname: Hartnett, Patrick E. organization: Department of Chemistry and Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University, Evanston, USA – sequence: 2 givenname: Scott M. surname: Dyar fullname: Dyar, Scott M. organization: Department of Chemistry and Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University, Evanston, USA – sequence: 3 givenname: Eric A. surname: Margulies fullname: Margulies, Eric A. organization: Department of Chemistry and Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University, Evanston, USA – sequence: 4 givenname: Leah E. surname: Shoer fullname: Shoer, Leah E. organization: Department of Chemistry and Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University, Evanston, USA – sequence: 5 givenname: Andrew W. surname: Cook fullname: Cook, Andrew W. organization: Department of Chemistry and Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University, Evanston, USA – sequence: 6 givenname: Samuel W. surname: Eaton fullname: Eaton, Samuel W. organization: Department of Chemistry and Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University, Evanston, USA – sequence: 7 givenname: Tobin J. surname: Marks fullname: Marks, Tobin J. organization: Department of Chemistry and Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University, Evanston, USA – sequence: 8 givenname: Michael R. surname: Wasielewski fullname: Wasielewski, Michael R. organization: Department of Chemistry and Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University, Evanston, USA |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/28936299$$D View this record in MEDLINE/PubMed https://www.osti.gov/servlets/purl/1164941$$D View this record in Osti.gov |
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| Snippet | The photophysics of a covalently linked perylenediimide–diketopyrrolopyrrole–perylenediimide acceptor–donor–acceptor molecule (PDI–DPP–PDI,
1
) were... The photophysics of a covalently linked perylenediimide-diketopyrrolopyrrole-perylenediimide acceptor-donor-acceptor molecule (PDI-DPP-PDI, ) were investigated... The photophysics of a covalently linked perylenediimide-diketopyrrolopyrrole-perylenediimide acceptor-donor-acceptor molecule (PDI-DPP-PDI, 1) were... The photophysics of a covalently linked perylenediimide–diketopyrrolopyrrole–perylenediimide acceptor–donor–acceptor molecule (PDI–DPP–PDI, 1) were... Self-ordering of covalent electron donor–acceptor building blocks in thin films upon solvent vapor annealing results in a 10 4 increase in photo-generated... |
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| SubjectTerms | Annealing Charge Charge carriers Chemistry Covalence Dynamical systems Dynamics Formations INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY Separation SOLAR ENERGY |
| Title | Long-lived charge carrier generation in ordered films of a covalent perylenediimide–diketopyrrolopyrrole–perylenediimide molecule |
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