scholarly journals Substituent Effects on Singlet Exciton Fission in Polycrystalline Thin Films of Cyano-Substituted Diaryltetracenes

2017 ◽  
Vol 121 (39) ◽  
pp. 21262-21271 ◽  
Author(s):  
Eric A. Margulies ◽  
Nicolas Kerisit ◽  
Przemyslaw Gawel ◽  
Catherine M. Mauck ◽  
Lin Ma ◽  
...  
Keyword(s):  
Thin Films ◽  
Substituent Effects ◽  
Singlet Exciton ◽  
Polycrystalline Thin Films ◽  
Singlet Exciton Fission

Singlet Exciton Fission in Polycrystalline Thin Films of a Slip-Stacked Perylenediimide

2013 ◽  
Vol 135 (39) ◽  
pp. 14701-14712 ◽  
Author(s):  
Samuel W. Eaton ◽  
Leah E. Shoer ◽  
Steven D. Karlen ◽  
Scott M. Dyar ◽  
Eric A. Margulies ◽  
...  
Keyword(s):  
Thin Films ◽  
Singlet Exciton ◽  
Polycrystalline Thin Films ◽  
Singlet Exciton Fission

Morphology-Independent Efficient Singlet Exciton Fission in Perylene Diimide Thin Films

ChemPlusChem ◽  
2018 ◽  
Vol 83 (4) ◽  
pp. 230-238 ◽  
Author(s):  
Yaroslav V. Aulin ◽  
Kevin M. Felter ◽  
D. Deniz Günbas ◽  
Rajeev K. Dubey ◽  
Wolter F. Jager ◽  
...  
Keyword(s):  
Thin Films ◽  
Perylene Diimide ◽  
Singlet Exciton ◽  
Singlet Exciton Fission

scholarly journals Singlet exciton fission via an intermolecular charge transfer state in coevaporated pentacene-perfluoropentacene thin films

2019 ◽  
Vol 151 (16) ◽  
pp. 164706 ◽  
Author(s):  
Vincent O. Kim ◽  
Katharina Broch ◽  
Valentina Belova ◽  
Y. S. Chen ◽  
Alexander Gerlach ◽  
...  
Keyword(s):  
Thin Films ◽  
Charge Transfer ◽  
Charge Transfer State ◽  
Singlet Exciton ◽  
Intermolecular Charge Transfer ◽  
Singlet Exciton Fission ◽  
Transfer State

scholarly journals Strategies for Design of Potential Singlet Fission Chromophores Utilizing a Combination of Ground State and Excited State Aromaticity Rules

2020 ◽  
Author(s):  
Ouissam El Bakouri ◽  
Joshua R. Smith ◽  
Henrik Ottosson
Keyword(s):  
Excited State ◽  
Excited States ◽  
Ground State ◽  
Geometric Model ◽  
Substituent Effects ◽  
Singlet Fission ◽  
Singlet Exciton ◽  
Singlet Exciton Fission ◽  
Homo Lumo ◽  
Potential Use

Singlet exciton fission photovoltaics requires chromophores with their lowest excited states arranged so that 2<i>E</i>(T<sub>1</sub>) < <i>E</i>(S<sub>1</sub>) and <i>E</i>(S<sub>1</sub>) < <i>E</i>(T<sub>2</sub>). Herein, qualitative theory and quantum chemical calculations are used to develop explicit strategies on how to use Baird’s 4<i>n</i> rule on excited state aromaticity, combined with Hückel’s 4<i>n</i>+2 rule for ground state aromaticity, to tailor new potential chromophores for singlet fission. We first analyze the <i>E</i>(T<sub>1</sub>), <i>E</i>(S<sub>1</sub>) and <i>E</i>(T<sub>2</sub>) of benzene and cyclobutadiene (<b>CBD</b>) as, respectively, excited state antiaromatic and aromatic archetypes, and reveal that <b>CBD </b>fulfils the criteria on the state ordering for a singlet fission chromophore. We then look at fulvenes, a class of compounds that can be tuned by choice of substituents from Baird-antiaromatic to Baird-aromatic in T<sub>1</sub> and S<sub>1</sub>, and from Hückel-aromatic to Hückel-antiaromatic in S<sub>0</sub>. The T<sub>1</sub> and S<sub>1</sub> states of most substituted fulvenes (159 of 225) are described by singly excited HOMO→LUMO configurations, providing a rational for the simultaneous tuning of <i>E</i>(T<sub>1</sub>) and <i>E</i>(S<sub>1</sub>) along an approximate (anti)aromaticity coordinate. Key to the tunability is the exchange integral (K<sub>H,L</sub>), which ideally is constant throughout the compound class, providing a constant D<i>E</i>(S<sub>1</sub>-T<sub>1</sub>). This leads us to a geometric model for identification of singlet fission chromophores, and we explore what factors limit the model. Candidates with calculated <i>E</i>(T<sub>1</sub>) of ~1 eV or higher are identified among benzannelated 4<i>n</i>pi-electron compound classes and siloles. In brief, it is clarified how the joint utilization of Baird’s 4<i>n</i> and Hückel’s 4<i>n</i>+2 rules, together with substituent effects (electronic and steric) and benzannelation, can be used to tailor new chromophores with potential use in singlet fission photovoltaics.<br>

scholarly journals Strategies for Design of Potential Singlet Fission Chromophores Utilizing a Combination of Ground State and Excited State Aromaticity Rules

2020 ◽  
Author(s):  
Ouissam El Bakouri ◽  
Joshua R. Smith ◽  
Henrik Ottosson
Keyword(s):  
Excited State ◽  
Excited States ◽  
Ground State ◽  
Geometric Model ◽  
Substituent Effects ◽  
Singlet Fission ◽  
Singlet Exciton ◽  
Singlet Exciton Fission ◽  
Homo Lumo ◽  
Potential Use

Singlet exciton fission photovoltaics requires chromophores with their lowest excited states arranged so that 2<i>E</i>(T<sub>1</sub>) < <i>E</i>(S<sub>1</sub>) and <i>E</i>(S<sub>1</sub>) < <i>E</i>(T<sub>2</sub>). Herein, qualitative theory and quantum chemical calculations are used to develop explicit strategies on how to use Baird’s 4<i>n</i> rule on excited state aromaticity, combined with Hückel’s 4<i>n</i>+2 rule for ground state aromaticity, to tailor new potential chromophores for singlet fission. We first analyze the <i>E</i>(T<sub>1</sub>), <i>E</i>(S<sub>1</sub>) and <i>E</i>(T<sub>2</sub>) of benzene and cyclobutadiene (<b>CBD</b>) as, respectively, excited state antiaromatic and aromatic archetypes, and reveal that <b>CBD </b>fulfils the criteria on the state ordering for a singlet fission chromophore. We then look at fulvenes, a class of compounds that can be tuned by choice of substituents from Baird-antiaromatic to Baird-aromatic in T<sub>1</sub> and S<sub>1</sub>, and from Hückel-aromatic to Hückel-antiaromatic in S<sub>0</sub>. The T<sub>1</sub> and S<sub>1</sub> states of most substituted fulvenes (159 of 225) are described by singly excited HOMO→LUMO configurations, providing a rational for the simultaneous tuning of <i>E</i>(T<sub>1</sub>) and <i>E</i>(S<sub>1</sub>) along an approximate (anti)aromaticity coordinate. Key to the tunability is the exchange integral (K<sub>H,L</sub>), which ideally is constant throughout the compound class, providing a constant D<i>E</i>(S<sub>1</sub>-T<sub>1</sub>). This leads us to a geometric model for identification of singlet fission chromophores, and we explore what factors limit the model. Candidates with calculated <i>E</i>(T<sub>1</sub>) of ~1 eV or higher are identified among benzannelated 4<i>n</i>pi-electron compound classes and siloles. In brief, it is clarified how the joint utilization of Baird’s 4<i>n</i> and Hückel’s 4<i>n</i>+2 rules, together with substituent effects (electronic and steric) and benzannelation, can be used to tailor new chromophores with potential use in singlet fission photovoltaics.<br>

Effects of Crystal Morphology on Singlet Exciton Fission in Diketopyrrolopyrrole Thin Films

2016 ◽  
Vol 120 (7) ◽  
pp. 1357-1366 ◽  
Author(s):  
Patrick E. Hartnett ◽  
Eric A. Margulies ◽  
Catherine M. Mauck ◽  
Stephen A. Miller ◽  
Yilei Wu ◽  
...  
Keyword(s):  
Thin Films ◽  
Crystal Morphology ◽  
Singlet Exciton ◽  
Singlet Exciton Fission

Strategies for Design of Potential Singlet Fission Chromophores Utilizing Baird's Rule on Excited State Aromaticity

2019 ◽  
Author(s):  
Ouissam El Bakouri ◽  
Joshua R. Smith ◽  
Henrik Ottosson
Keyword(s):  
Excited State ◽  
Excited States ◽  
Geometric Model ◽  
Substituent Effects ◽  
Singlet Fission ◽  
Singlet Exciton ◽  
Technology Platforms ◽  
Singlet Exciton Fission ◽  
Homo Lumo ◽  
Potential Use

In singlet exciton fission one photon of light is used to create two excitons of triplet multiplicity. This process requires chromophores with their lowest excited states arranged so that 2<i>E</i>(T<sub>1</sub>) < <i>E</i>(S<sub>1</sub>) and <i>E</i>(S<sub>1</sub>) < <i>E</i>(T<sub>2</sub>). To match different technology platforms there is a high need for new candidate chromophores with the desired excited state orderings. Herein, qualitative theory and quantum chemical calculations are used to develop explicit strategies on how to use Baird’s 4n rule on excited state aromaticity to tailor new potential chromophores for singlet fission. We first analyze the <i>E</i>(T<sub>1</sub>), <i>E</i>(S<sub>1</sub>) and <i>E</i>(T<sub>2</sub>) of benzene and cyclobutadiene (CBD) as, respectively, excited state antiaromatic and aromatic archetypes, and reveal that CBD fulfils the criteria on the state ordering for a singlet fission chromophore. We then look at fulvenes, a class of compounds that can be tuned from Baird-antiaromatic to Baird-aromatic in T<sub>1</sub> and S<sub>1</sub> by choice of substituents. The T<sub>1</sub> and S<sub>1</sub> states of fulvenes are both described by singly excited HOMO→LUMO configurations, which provides a rational for the simultaneous and similar tuning of <i>E</i>(T<sub>1</sub>) and <i>E</i>(S<sub>1</sub>) along an approximate (anti)aromaticity coordinate. This leads us to a geometric model for identification of singlet fission chromophores. Candidates with calculated <i>E</i>(T<sub>1</sub>) of ~1 eV or higher are also identified among benzannelated 4<i>n</i>pi-electron compound classes and among siloles influenced to various extents by Baird-(anti)aromaticity in T<sub>1</sub> and S<sub>1</sub>. Finally, we explore the limitations of the design approach. In brief, it is clarified how Baird’s 4<i>n</i> rule together with substituent effects (electronic and steric) and benzannelation can be used to tailor new chromophores with potential use in singlet fission photovoltaics. <br>

scholarly journals Cover Feature: Morphology-Independent Efficient Singlet Exciton Fission in Perylene Diimide Thin Films (ChemPlusChem 4/2018)

ChemPlusChem ◽  
2018 ◽  
Vol 83 (4) ◽  
pp. 141-141
Author(s):  
Yaroslav V. Aulin ◽  
Kevin M. Felter ◽  
D. Deniz Günbas ◽  
Rajeev K. Dubey ◽  
Wolter F. Jager ◽  
...  
Keyword(s):  
Thin Films ◽  
Perylene Diimide ◽  
Singlet Exciton ◽  
Singlet Exciton Fission

Singlet Exciton Fission in Thin Films of tert-Butyl-Substituted Terrylenes

2015 ◽  
Vol 119 (18) ◽  
pp. 4151-4161 ◽  
Author(s):  
Samuel W. Eaton ◽  
Stephen A. Miller ◽  
Eric A. Margulies ◽  
Leah E. Shoer ◽  
Richard D. Schaller ◽  
...  
Keyword(s):  
Thin Films ◽  
Singlet Exciton ◽  
Tert Butyl ◽  
Singlet Exciton Fission
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