Robust singlet fission in pentacene thin films with tuned charge transfer interactions

Singlet fission, the spin-allowed photophysical process converting an excited singlet state into two triplet states, has attracted significant attention for device applications. Research so far has focused mainly on the understanding of singlet fission in pure materials, yet blends offer the promise...

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Published in:Nature communications Vol. 9; no. 1; pp. 954 - 9
Main Authors: Broch, K., Dieterle, J., Branchi, F., Hestand, N. J., Olivier, Y., Tamura, H., Cruz, C., Nichols, V. M., Hinderhofer, A., Beljonne, D., Spano, F. C., Cerullo, G., Bardeen, C. J., Schreiber, F.
Format: Journal Article
Language:English
Published: London Nature Publishing Group UK 05.03.2018
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Subjects:
132/122
140/125
639/301/923/3931
639/638/440/949
Charge transfer
Chemistry
Fission
Humanities and Social Sciences
Mixtures
multidisciplinary
Optical properties
Science
Science (multidisciplinary)
Thin films
ISSN:2041-1723, 2041-1723
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Abstract Singlet fission, the spin-allowed photophysical process converting an excited singlet state into two triplet states, has attracted significant attention for device applications. Research so far has focused mainly on the understanding of singlet fission in pure materials, yet blends offer the promise of a controlled tuning of intermolecular interactions, impacting singlet fission efficiencies. Here we report a study of singlet fission in mixtures of pentacene with weakly interacting spacer molecules. Comparison of experimentally determined stationary optical properties and theoretical calculations indicates a reduction of charge-transfer interactions between pentacene molecules with increasing spacer molecule fraction. Theory predicts that the reduced interactions slow down singlet fission in these blends, but surprisingly we find that singlet fission occurs on a timescale comparable to that in pure crystalline pentacene. We explain the observed robustness of singlet fission in such mixed films by a mechanism of exciton diffusion to hot spots with closer intermolecular spacings. Singlet fission is desirable for highly efficient solar cells, yet the details of the process remain elusive. Here, Broch et al. show that the changes in bulk intermolecular interactions can have little effect on the singlet fission rate in a mixture of pentacene and weakly interacting spacer molecules.
AbstractList Singlet fission, the spin-allowed photophysical process converting an excited singlet state into two triplet states, has attracted significant attention for device applications. Research so far has focused mainly on the understanding of singlet fission in pure materials, yet blends offer the promise of a controlled tuning of intermolecular interactions, impacting singlet fission efficiencies. Here we report a study of singlet fission in mixtures of pentacene with weakly interacting spacer molecules. Comparison of experimentally determined stationary optical properties and theoretical calculations indicates a reduction of charge-transfer interactions between pentacene molecules with increasing spacer molecule fraction. Theory predicts that the reduced interactions slow down singlet fission in these blends, but surprisingly we find that singlet fission occurs on a timescale comparable to that in pure crystalline pentacene. We explain the observed robustness of singlet fission in such mixed films by a mechanism of exciton diffusion to hot spots with closer intermolecular spacings.
Singlet fission, the spin-allowed photophysical process converting an excited singlet state into two triplet states, has attracted significant attention for device applications. Research so far has focused mainly on the understanding of singlet fission in pure materials, yet blends offer the promise of a controlled tuning of intermolecular interactions, impacting singlet fission efficiencies. Here we report a study of singlet fission in mixtures of pentacene with weakly interacting spacer molecules. Comparison of experimentally determined stationary optical properties and theoretical calculations indicates a reduction of charge-transfer interactions between pentacene molecules with increasing spacer molecule fraction. Theory predicts that the reduced interactions slow down singlet fission in these blends, but surprisingly we find that singlet fission occurs on a timescale comparable to that in pure crystalline pentacene. We explain the observed robustness of singlet fission in such mixed films by a mechanism of exciton diffusion to hot spots with closer intermolecular spacings.Singlet fission, the spin-allowed photophysical process converting an excited singlet state into two triplet states, has attracted significant attention for device applications. Research so far has focused mainly on the understanding of singlet fission in pure materials, yet blends offer the promise of a controlled tuning of intermolecular interactions, impacting singlet fission efficiencies. Here we report a study of singlet fission in mixtures of pentacene with weakly interacting spacer molecules. Comparison of experimentally determined stationary optical properties and theoretical calculations indicates a reduction of charge-transfer interactions between pentacene molecules with increasing spacer molecule fraction. Theory predicts that the reduced interactions slow down singlet fission in these blends, but surprisingly we find that singlet fission occurs on a timescale comparable to that in pure crystalline pentacene. We explain the observed robustness of singlet fission in such mixed films by a mechanism of exciton diffusion to hot spots with closer intermolecular spacings.
Singlet fission is desirable for highly efficient solar cells, yet the details of the process remain elusive. Here, Broch et al. show that the changes in bulk intermolecular interactions can have little effect on the singlet fission rate in a mixture of pentacene and weakly interacting spacer molecules.
Singlet fission, the spin-allowed photophysical process converting an excited singlet state into two triplet states, has attracted significant attention for device applications. Research so far has focused mainly on the understanding of singlet fission in pure materials, yet blends offer the promise of a controlled tuning of intermolecular interactions, impacting singlet fission efficiencies. Here we report a study of singlet fission in mixtures of pentacene with weakly interacting spacer molecules. Comparison of experimentally determined stationary optical properties and theoretical calculations indicates a reduction of charge-transfer interactions between pentacene molecules with increasing spacer molecule fraction. Theory predicts that the reduced interactions slow down singlet fission in these blends, but surprisingly we find that singlet fission occurs on a timescale comparable to that in pure crystalline pentacene. We explain the observed robustness of singlet fission in such mixed films by a mechanism of exciton diffusion to hot spots with closer intermolecular spacings. Singlet fission is desirable for highly efficient solar cells, yet the details of the process remain elusive. Here, Broch et al. show that the changes in bulk intermolecular interactions can have little effect on the singlet fission rate in a mixture of pentacene and weakly interacting spacer molecules.
Singlet fission, the spin-allowed photophysical process converting an excited singlet state into two triplet states, has attracted significant attention for device applications. Research so far has focused mainly on the understanding of singlet fission in pure materials, yet blends offer the promise of a controlled tuning of intermolecular interactions, impacting singlet fission efficiencies. Here we report a study of singlet fission in mixtures of pentacene with weakly interacting spacer molecules. Comparison of experimentally determined stationary optical properties and theoretical calculations indicates a reduction of charge-transfer interactions between pentacene molecules with increasing spacer molecule fraction. Theory predicts that the reduced interactions slow down singlet fission in these blends, but surprisingly we find that singlet fission occurs on a timescale comparable to that in pure crystalline pentacene. We explain the observed robustness of singlet fission in such mixed films by a mechanism of exciton diffusion to hot spots with closer intermolecular spacings. Singlet fission is desirable for highly efficient solar cells, yet the details of the process remain elusive. Here, Broch et al. show that the changes in bulk intermolecular interactions can have little effect on the singlet fission rate in a mixture of pentacene and weakly interacting spacer molecules.
ArticleNumber 954
Author Hinderhofer, A.
Broch, K.
Hestand, N. J.
Tamura, H.
Spano, F. C.
Schreiber, F.
Cerullo, G.
Cruz, C.
Beljonne, D.
Branchi, F.
Nichols, V. M.
Dieterle, J.
Olivier, Y.
Bardeen, C. J.
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/29507287$$D View this record in MEDLINE/PubMed
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MendezHCharge-transfer crystallites as molecular electrical dopantsNat. Commun.201561:CAS:528:DC%2BC2MXhs1Skt7nF10.1038/ncomms9560264404034600739
BaselBSUnified model for singlet fission within a non-conjugated covalent pentacene dimerNat. Commun.201782017NatCo...815171B1:CAS:528:DC%2BC2sXotFyju7w%3D10.1038/ncomms15171285169165493541
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HestandNPolarized absorption in crystalline pentacene: theory vs. experimentJ. Phys. Chem. C201511922137221471:CAS:528:DC%2BC2MXhsFSitrfK10.1021/acs.jpcc.5b07163
BakulinAAReal-time observation of multiexcitonic states in ultrafast singlet fission using coherent 2D electronic spectroscopyNat. Chem.20168161:CAS:528:DC%2BC2MXhslantLzP10.1038/nchem.237126673260
LukmanSTuning the role of charge-transfer states in intramolecular singlet exciton fission through side-group engineeringNat. Commun.201672016NatCo...713622L1:CAS:528:DC%2BC28XitFWnsLjF10.1038/ncomms13622279248195150654
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BrochKOptical properties of blends: Influence of mixing-induced disorder in pentacene:diindenoperylene vs. perfluoropentacene:diindenoperyleneJ. Phys. Chem. C2013117139521:CAS:528:DC%2BC3sXpsVOntL0%3D10.1021/jp4019487
BerkelbachTCHybertsenMSReichmanDRMicroscopic theory of singlet exciton fission. III. Crystalline pentaceneJ. Chem. Phys.20141410747052014JChPh.141g4705B10.1063/1.489279325149804
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HesseRHofbergerWBässlerHAbsorption spectra of disordered solid tetracene and pentaceneChem. Phys.1980492012111980CP.....49..201H1:CAS:528:DyaL3cXkvVCgsLY%3D10.1016/0301-0104(80)85257-8
PolliPLuerLCerulloGHigh-time-resolution pump-probe system with broadband detection for the study of time-domain vibrational dynamicsRev. Sci. Instrum.2007781031082007RScI...78j3108P10.1063/1.280077817979407
MeyerHDMantheUCederbaumLSThe multi-configuration time-dependent Hartree approachChem. Phys. Lett.1990165731990CPL...165...73M1:CAS:528:DyaK3cXht1Gns7w%3D10.1016/0009-2614(90)87014-I0816.65116
NakayamaYDetermination of the highest occupied molecular orbital energy of pentacene single crystals by ultraviolet photoelectron and photoelectron yield spectroscopiesJpn. J. Appl. Sci.20145301AD0310.7567/JJAP.53.01AD03
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KuzmenkoAKramers-Kronig contrained variational analysis of optical spectraRev. Sci. Instrum.2005760831082005RScI...76h3108K10.1063/1.1979470
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TianXNanoscale exponential distance dependence and electron-transfer model for intermolecular singlet exciton fission observed in rubrene-doped organic filmsOrg. Electron.2017504291:CAS:528:DC%2BC2sXhsVWhtL7N10.1016/j.orgel.2017.08.009
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Brütting, W. & Adachi, C. Physics of Organic Semiconductors 2nd edn. (Wiley, Weinheim, 2012).
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YostSRA transferable model for singlet-fission kineticsNat. Chem.201464921:CAS:528:DC%2BC2cXntlyisL8%3D10.1038/nchem.194524848234
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UenoNKeraSElectron spectroscopy of functional organic thin films: deep insights into valence electronic structure in relation to charge transport propertyProg. Surf. Sci.2008834902008PrSS...83..490U1:CAS:528:DC%2BD1cXhsVWhtL7I10.1016/j.progsurf.2008.10.002
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PoletayevADTriplet dynamics in pentacene crystals: Applications to fission-sensitized photovoltaicsAdv. Mater.2014269191:CAS:528:DC%2BC3sXitVShsLbL10.1002/adma.20130242724375546
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KazmaierPHoffmannRA theoretical study of crystallochromy. Quantum interference effects in the spectra of perylene pigmentsJ. Am. Chem. Soc.199411696841:CAS:528:DyaK2cXmtVOlt7o%3D10.1021/ja00100a038
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A Kuzmenko (3300_CR50) 2005; 76
T Hosokai (3300_CR24) 2015; 119
Y Nakayama (3300_CR23) 2014; 53
S Lukman (3300_CR19) 2015; 25
AD Poletayev (3300_CR39) 2014; 26
C Sutton (3300_CR12) 2017; 29
BS Basel (3300_CR10) 2017; 8
JL Bredas (3300_CR2) 2004; 104
BJ Walker (3300_CR42) 2013; 5
H Marciniak (3300_CR38) 2009; 79
VM Nichols (3300_CR30) 2015; 119
HD Meyer (3300_CR35) 1990; 165
N Ueno (3300_CR27) 2008; 83
M Smith (3300_CR7) 2010; 110
MWB Wilson (3300_CR17) 2011; 133
R Forker (3300_CR51) 2012; 108
3300_CR1
J Dieterle (3300_CR22) 2015; 119
X Tian (3300_CR47) 2017; 50
M Tayebjee (3300_CR14) 2016; 120
H Yamagata (3300_CR32) 2011; 134
SR Yost (3300_CR20) 2014; 6
WN Han (3300_CR25) 2013; 103
L Wang (3300_CR46) 2014; 5
K Broch (3300_CR28) 2013; 117
H Tamura (3300_CR36) 2015; 115
TC Berkelbach (3300_CR6) 2014; 141
S Fanetti (3300_CR29) 2012; 137
EC Greyson (3300_CR8) 2010; 114
SN Sanders (3300_CR40) 2015; 137
P Petelenz (3300_CR44) 2016; 7
M Delgado (3300_CR33) 2009; 131
P Polli (3300_CR52) 2007; 78
R Hesse (3300_CR5) 1980; 49
S Lukman (3300_CR18) 2016; 7
MWB Wilson (3300_CR16) 2013; 46
ST Roberts (3300_CR15) 2012; 134
D Beljonne (3300_CR4) 2013; 110
EA Buchanan (3300_CR34) 2017; 75
EG Fuemmeler (3300_CR13) 2016; 2
M Castellanos (3300_CR45) 2017; 8
G Piland (3300_CR43) 2015; 6
N Hestand (3300_CR3) 2015; 119
H Proehl (3300_CR48) 2005; 71
AA Bakulin (3300_CR9) 2016; 8
H Mendez (3300_CR26) 2015; 6
BA West (3300_CR37) 2010; 114
P Kazmaier (3300_CR31) 1994; 116
AF Schwerin (3300_CR11) 2010; 114
R Nitsche (3300_CR49) 2004; 70
A Aufderheide (3300_CR21) 2012; 109
J Zirzlmeier (3300_CR41) 2015; 112
References_xml – reference: PilandGBardeenCJHow morphology affects singlet fission in crystalline tetraceneJ. Phys. Chem. Lett.2015618411:CAS:528:DC%2BC2MXntF2kur4%3D10.1021/acs.jpclett.5b0056926263258
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– reference: DieterleJStructural properties of picene-perfluoropentacene and picene-pentacene blends: superlattice formation versus limited intermixingJ. Phys. Chem. C2015119263391:CAS:528:DC%2BC2MXhslWjsrbL10.1021/acs.jpcc.5b08866
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– reference: FuemmelerEGA direct mechanism of ultrafast intramolecular singlet fission in pentacene dimersACS Cent. Sci.2016232610.1021/acscentsci.6b00063
– reference: WilsonMWBUltrafast dynamics of exciton fission in polycrystalline pentaceneJ. Am. Chem. Soc.2011133118301:CAS:528:DC%2BC3MXovVegtr8%3D10.1021/ja201688h21755937
– reference: TianXNanoscale exponential distance dependence and electron-transfer model for intermolecular singlet exciton fission observed in rubrene-doped organic filmsOrg. Electron.2017504291:CAS:528:DC%2BC2sXhsVWhtL7N10.1016/j.orgel.2017.08.009
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– reference: KazmaierPHoffmannRA theoretical study of crystallochromy. Quantum interference effects in the spectra of perylene pigmentsJ. Am. Chem. Soc.199411696841:CAS:528:DyaK2cXmtVOlt7o%3D10.1021/ja00100a038
– reference: LukmanSTuneable singlet exciton fission and triplet-triplet annihilation in an orthogonal pentacene-dimerAdv. Funct. Mater.20152554521:CAS:528:DC%2BC2MXht1KrurjM10.1002/adfm.201501537
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– reference: ZirzlmeierJSinglet fission in pentacene dimersProc. Natl Acad. Sci. USA201511253252015PNAS..112.5325Z1:CAS:528:DC%2BC2MXmt1SntrY%3D10.1073/pnas.1422436112258589544418859
– reference: UenoNKeraSElectron spectroscopy of functional organic thin films: deep insights into valence electronic structure in relation to charge transport propertyProg. Surf. Sci.2008834902008PrSS...83..490U1:CAS:528:DC%2BD1cXhsVWhtL7I10.1016/j.progsurf.2008.10.002
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– reference: MeyerHDMantheUCederbaumLSThe multi-configuration time-dependent Hartree approachChem. Phys. Lett.1990165731990CPL...165...73M1:CAS:528:DyaK3cXht1Gns7w%3D10.1016/0009-2614(90)87014-I0816.65116
– reference: FanettiSHOMO-LUMO transitions in solvated and crystalline piceneJ. Chem. Phys.20121372245062012JChPh.137v4506F10.1063/1.477026523249016
– reference: YamagataHThe nature of singlet excitons in oligoacene molecular crystalsJ. Chem. Phys.20111342047032011JChPh.134t4703Y1:STN:280:DC%2BC3MjgtlOlsw%3D%3D10.1063/1.359087121639463
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– reference: SmithMMichlJSinglet fissionChem. Rev.2010110689169361:CAS:528:DC%2BC3cXhtlKntbbF10.1021/cr100261321053979
– reference: BuchananEAHavlasZMichlJSinglet fission: optimiziation of chromophore dimer geometryAdv. Quant. Chem.2017751751:CAS:528:DC%2BC1cXitlWgs7w%3D10.1016/bs.aiq.2017.03.005
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– reference: HesseRHofbergerWBässlerHAbsorption spectra of disordered solid tetracene and pentaceneChem. Phys.1980492012111980CP.....49..201H1:CAS:528:DyaL3cXkvVCgsLY%3D10.1016/0301-0104(80)85257-8
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– reference: YostSRA transferable model for singlet-fission kineticsNat. Chem.201464921:CAS:528:DC%2BC2cXntlyisL8%3D10.1038/nchem.194524848234
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– reference: ProehlHNitscheRDienelTLeoKFritzTIn situ differential reflectance spectroscopy of thin crystalline films of PTCDA on different substratesPhys. Rev. B2005711652072005PhRvB..71p5207P10.1103/PhysRevB.71.165207
– reference: SchwerinAFToward designed singlet fission: electronic states and photophysics of 1,3-diphenylisobenzofuranJ. Phys. Chem. A201011414571:CAS:528:DC%2BD1MXhsFylurzJ10.1021/jp907401t20025258
– reference: LukmanSTuning the role of charge-transfer states in intramolecular singlet exciton fission through side-group engineeringNat. Commun.201672016NatCo...713622L1:CAS:528:DC%2BC28XitFWnsLjF10.1038/ncomms13622279248195150654
– reference: MarciniakHPugliesiINickelBLochbrunnerSUltrafast singlet and triplet dynamics in microcrystalline pentacene filmsPhys. Rev. B2009792353182009PhRvB..79w5318M10.1103/PhysRevB.79.235318
– reference: PoletayevADTriplet dynamics in pentacene crystals: Applications to fission-sensitized photovoltaicsAdv. Mater.2014269191:CAS:528:DC%2BC3sXitVShsLbL10.1002/adma.20130242724375546
– reference: KuzmenkoAKramers-Kronig contrained variational analysis of optical spectraRev. Sci. Instrum.2005760831082005RScI...76h3108K10.1063/1.1979470
– reference: BaselBSUnified model for singlet fission within a non-conjugated covalent pentacene dimerNat. Commun.201782017NatCo...815171B1:CAS:528:DC%2BC2sXotFyju7w%3D10.1038/ncomms15171285169165493541
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– reference: HosokaiTThickness and substrate dependent thin films growth of picene and impact to the electronic structureJ. Phys. Chem. C2015119290271:CAS:528:DC%2BC2MXhvFGnsrzL10.1021/acs.jpcc.5b10453
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– reference: RobertsSTEfficient singlet fission discovered in a disordered acene filmJ. Am. Chem. Soc.201213463881:CAS:528:DC%2BC38XktFelu78%3D10.1021/ja300504t22432700
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Snippet Singlet fission, the spin-allowed photophysical process converting an excited singlet state into two triplet states, has attracted significant attention for...
Singlet fission is desirable for highly efficient solar cells, yet the details of the process remain elusive. Here, Broch et al. show that the changes in bulk...
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SubjectTerms 132/122
140/125
639/301/923/3931
639/638/440/949
Charge transfer
Chemistry
Fission
Humanities and Social Sciences
Mixtures
multidisciplinary
Optical properties
Science
Science (multidisciplinary)
Thin films
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Title Robust singlet fission in pentacene thin films with tuned charge transfer interactions
URI https://link.springer.com/article/10.1038/s41467-018-03300-1
https://www.ncbi.nlm.nih.gov/pubmed/29507287
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