Singlet Fission and Excimer Formation in Disordered Solids of Alkyl-Substituted 1,3-Diphenylisobenzofurans

Dron, Paul I.; Michl, Josef; Johnson, Justin C.

doi:10.1021/acs.jpca.7b07362

Title: Singlet Fission and Excimer Formation in Disordered Solids of Alkyl-Substituted 1,3-Diphenylisobenzofurans

Abstract

Here, we describe the preparation and excited state dynamics of three alkyl derivatives of 1,3-diphenylisobenzofuran (1) in both solutions and thin films. The substitutions are intended to disrupt the slip-stacked packing observed in crystals of 1 while maintaining the favorable energies of singlet and triplet for singlet fission (SF). All substitutions result in films that are largely amorphous as judged by the absence of strong X-ray diffraction peaks. The films of 1 carrying a methyl in the para position of one phenyl ring undergo SF relatively efficiently (≥75% triplet yield, Φ_T) but more slowly than thin films of 1. When the methyl is replaced with a t-butyl, kinetic competition in the excited state favors excimer formation rather than SF (Φ_T = 55%). When t-Bu groups are placed in both meta positions of the phenyl substituent, SF is slowed further and Φ_T =

Authors:

Dron, Paul I. ^[1];

^[2];

^[3]

Univ. of Colorado, Boulder, CO (United States). Dept. of Chemistry and Biochemistry
Univ. of Colorado, Boulder, CO (United States). Dept. of Chemistry and Biochemistry; y, Academy of Sciences of the Czech Republic, Prague (Czech Republic). Inst. of Organic Chemistry and Biochemistry
National Renewable Energy Lab. (NREL), Golden, CO (United States)

Publication Date:: 2017-10-16

Research Org.:: National Renewable Energy Lab. (NREL), Golden, CO (United States); Univ. of Colorado, Boulder, CO (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

OSTI Identifier:: 1409160

Alternate Identifier(s):: OSTI ID: 1688390

Report Number(s):: NREL/JA-5900-68951
Journal ID: ISSN 1089-5639

Grant/Contract Number:: AC36-08GO28308; SC0007004

Resource Type:: Accepted Manuscript

Journal Name:: Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory

Additional Journal Information:: Journal Volume: 121; Journal Issue: 45; Journal ID: ISSN 1089-5639

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; singlet fission; thin film; photophysics; triplet; excimer

Citation Formats


                    Dron, Paul I., Michl, Josef, and Johnson, Justin C.. Singlet Fission and Excimer Formation in Disordered Solids of Alkyl-Substituted 1,3-Diphenylisobenzofurans.  United States: N. p., 2017. 
Web.  doi:10.1021/acs.jpca.7b07362.

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                    Dron, Paul I., Michl, Josef, & Johnson, Justin C.. Singlet Fission and Excimer Formation in Disordered Solids of Alkyl-Substituted 1,3-Diphenylisobenzofurans.  United States.  https://doi.org/10.1021/acs.jpca.7b07362

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                    Dron, Paul I., Michl, Josef, and Johnson, Justin C.. Mon .  
"Singlet Fission and Excimer Formation in Disordered Solids of Alkyl-Substituted 1,3-Diphenylisobenzofurans".  United States.  https://doi.org/10.1021/acs.jpca.7b07362.  https://www.osti.gov/servlets/purl/1409160.

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@article{osti_1409160,

  title        = {Singlet Fission and Excimer Formation in Disordered Solids of Alkyl-Substituted 1,3-Diphenylisobenzofurans},

  author       = {Dron, Paul I. and Michl, Josef and Johnson, Justin C.},

  abstractNote = {Here, we describe the preparation and excited state dynamics of three alkyl derivatives of 1,3-diphenylisobenzofuran (1) in both solutions and thin films. The substitutions are intended to disrupt the slip-stacked packing observed in crystals of 1 while maintaining the favorable energies of singlet and triplet for singlet fission (SF). All substitutions result in films that are largely amorphous as judged by the absence of strong X-ray diffraction peaks. The films of 1 carrying a methyl in the para position of one phenyl ring undergo SF relatively efficiently (≥75% triplet yield, ΦT) but more slowly than thin films of 1. When the methyl is replaced with a t-butyl, kinetic competition in the excited state favors excimer formation rather than SF (ΦT = 55%). When t-Bu groups are placed in both meta positions of the phenyl substituent, SF is slowed further and ΦT =},

  doi          = {10.1021/acs.jpca.7b07362},

  journal      = {Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory},

  number       = 45,

  volume       = 121,

  place        = {United States},

  year         = {2017},

  month        = {10}

}

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Works referencing / citing this record:

Searching for Diradicaloid Chromophores with Efficient Singlet Fission: Cyano‐Group Substitution of Difuropyrene Systems
journal, May 2019

Li, Qing; Kan, Yu‐He; Wu, Xue
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Structure and photophysics of indigoids for singlet fission: Cibalackrot
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Korovina, Nadezhda V.; Pompetti, Nicholas F.; Johnson, Justin C.
The Journal of Chemical Physics, Vol. 152, Issue 4
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Title: Singlet Fission and Excimer Formation in Disordered Solids of Alkyl-Substituted 1,3-Diphenylisobenzofurans

Abstract

Citation Formats

Singlet Exciton Fission for Solar Cell Applications: Energy Aspects of Interchromophore Coupling † journal, November 2010

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Laser Generation of Excitons and Fluorescence in Anthracene Crystals journal, January 1965

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Solar conversion efficiency of photovoltaic and photoelectrolysis cells with carrier multiplication absorbers journal, October 2006

Photocurrent Enhanced by Singlet Fission in a Dye-Sensitized Solar Cell journal, January 2015

External Quantum Efficiency Above 100% in a Singlet-Exciton-Fission-Based Organic Photovoltaic Cell journal, April 2013

Multiple exciton generation in quantum dots versus singlet fission in molecular chromophores for solar photon conversion journal, June 2015

Toward Designed Singlet Fission: Electronic States and Photophysics of 1,3-Diphenylisobenzofuran † journal, January 2010

Singlet Fission for Dye-Sensitized Solar Cells: Can a Suitable Sensitizer Be Found? journal, December 2006

High Triplet Yield from Singlet Fission in a Thin Film of 1,3-Diphenylisobenzofuran journal, November 2010

Two Thin Film Polymorphs of the Singlet Fission Compound 1,3-Diphenylisobenzofuran journal, May 2014

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Direct Observation of a Charge-Transfer State Preceding High-Yield Singlet Fission in Terrylenediimide Thin Films journal, December 2016

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Singlet Fission in a Covalently Linked Cofacial Alkynyltetracene Dimer journal, January 2016

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Singlet Exciton Fission for Solar Cell Applications: Energy Aspects of Interchromophore Coupling ^†
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Recent Advances in Singlet Fission
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Laser Generation of Excitons and Fluorescence in Anthracene Crystals
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Bimolecular radiationless transitions in crystalline tetracene
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Solar conversion efficiency of photovoltaic and photoelectrolysis cells with carrier multiplication absorbers
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Photocurrent Enhanced by Singlet Fission in a Dye-Sensitized Solar Cell
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External Quantum Efficiency Above 100% in a Singlet-Exciton-Fission-Based Organic Photovoltaic Cell
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Multiple exciton generation in quantum dots versus singlet fission in molecular chromophores for solar photon conversion
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Excitation Localization/Delocalization Isomerism in a Strongly Coupled Covalent Dimer of 1,3-Diphenylisobenzofuran
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Toward Designed Singlet Fission: Solution Photophysics of Two Indirectly Coupled Covalent Dimers of 1,3-Diphenylisobenzofuran
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Dynamic Exchange During Triplet Transport in Nanocrystalline TIPS-Pentacene Films
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Quantitative Intramolecular Singlet Fission in Bipentacenes
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Direct Observation of a Charge-Transfer State Preceding High-Yield Singlet Fission in Terrylenediimide Thin Films
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