skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: 1,3-Diphenylisobenzofuran: a Model Chromophore for Singlet Fission

Abstract

In this review we first provide an introductory description of the singlet fission phenomenon and then describe the ground and electronically excited states of the parent 1,3-diphenylisobenzofuran chromophore (1) and about a dozen of its derivatives. A discussion of singlet fission in thin polycrystalline layers of these materials follows. The highest quantum yield of triplet formation by singlet fission, 200% at 80 K, is found in one of the two known crystal modification of the parent. In the other modification and in many derivatives, excimer formation competes successfully and triplet yields are low. A description of solution photophysics of covalent dimers is described in the next section. Triplet yields are very low, but interesting phenomena are uncovered. One is an observation of a separated-charges (charge-transfer) intermediate in highly polar solvents. The other is an observation of excitation isomerism in both singlet and triplet states, where in one isomer the excitation is delocalized over both halves of the covalent dimer, whereas in the other it is localized on one of the halves. Finally, in the last section we present the operation of a simple device illustrating the use of triplets generated by singlet fission for charge separation.

Authors:
ORCiD logo [1]; ORCiD logo [2]
  1. National Renewable Energy Lab. (NREL), Golden, CO (United States)
  2. Univ. of Colorado, Boulder, CO (United States). Dept. of Chemistry and Biochemistry; Academy of Sciences of the Czech Republic (ASCR), Prague (Czech Republic). Inst. of Organic Chemistry and Biochemistry
Publication Date:
Research Org.:
National Renewable Energy Lab. (NREL), Golden, CO (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1394736
Report Number(s):
NREL/JA-5900-68011
Journal ID: ISSN 2365-0869
Grant/Contract Number:  
AC36-08GO28308; SC0007004; GA15-19143S
Resource Type:
Journal Article: Accepted Manuscript
Journal Name:
Topics in Current Chemistry
Additional Journal Information:
Journal Volume: 375; Journal Issue: 5; Journal ID: ISSN 2365-0869
Publisher:
Springer
Country of Publication:
United States
Language:
English
Subject:
14 SOLAR ENERGY; 36 MATERIALS SCIENCE; 1,3-diphenylisobenzofuran; photophysics; solar energy; singlet fission; covalent dimers

Citation Formats

Johnson, Justin C., and Michl, Josef. 1,3-Diphenylisobenzofuran: a Model Chromophore for Singlet Fission. United States: N. p., 2017. Web. doi:10.1007/s41061-017-0162-3.
Johnson, Justin C., & Michl, Josef. 1,3-Diphenylisobenzofuran: a Model Chromophore for Singlet Fission. United States. https://doi.org/10.1007/s41061-017-0162-3
Johnson, Justin C., and Michl, Josef. 2017. "1,3-Diphenylisobenzofuran: a Model Chromophore for Singlet Fission". United States. https://doi.org/10.1007/s41061-017-0162-3. https://www.osti.gov/servlets/purl/1394736.
@article{osti_1394736,
title = {1,3-Diphenylisobenzofuran: a Model Chromophore for Singlet Fission},
author = {Johnson, Justin C. and Michl, Josef},
abstractNote = {In this review we first provide an introductory description of the singlet fission phenomenon and then describe the ground and electronically excited states of the parent 1,3-diphenylisobenzofuran chromophore (1) and about a dozen of its derivatives. A discussion of singlet fission in thin polycrystalline layers of these materials follows. The highest quantum yield of triplet formation by singlet fission, 200% at 80 K, is found in one of the two known crystal modification of the parent. In the other modification and in many derivatives, excimer formation competes successfully and triplet yields are low. A description of solution photophysics of covalent dimers is described in the next section. Triplet yields are very low, but interesting phenomena are uncovered. One is an observation of a separated-charges (charge-transfer) intermediate in highly polar solvents. The other is an observation of excitation isomerism in both singlet and triplet states, where in one isomer the excitation is delocalized over both halves of the covalent dimer, whereas in the other it is localized on one of the halves. Finally, in the last section we present the operation of a simple device illustrating the use of triplets generated by singlet fission for charge separation.},
doi = {10.1007/s41061-017-0162-3},
url = {https://www.osti.gov/biblio/1394736}, journal = {Topics in Current Chemistry},
issn = {2365-0869},
number = 5,
volume = 375,
place = {United States},
year = {2017},
month = {9}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Citation Metrics:
Cited by: 6 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

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


EPR of triplet excitions in tetracene crystals: spin polarization and the role of singlet exciton fission
journal, October 1972


Collective aspects of singlet fission in molecular crystals
journal, July 2015


A Versatile and Regiospecific Synthesis of Functionalized 1,3-Diarylisobenzofurans
journal, September 2008


Efficient Singlet Fission Discovered in a Disordered Acene Film
journal, March 2012


Different Rates of Singlet Fission in Monoclinic versus Orthorhombic Crystal Forms of Diphenylhexatriene
journal, November 2013


Bimolecular radiationless transitions in crystalline tetracene
journal, September 1968


Recent Advances in Singlet Fission
journal, April 2013


Exciton fission and annihilation in crystalline tetracene
journal, January 1977


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


Coexistence of Exciton Fission and Fusion in Tetracene Crystals
journal, January 1970


Magnetic field effect on prompt fluorescence in anthracene: evidence for singlet exciton fission
journal, October 1972


Determination of singlet oxygen quantum yields with 1,3-diphenylisobenzofuran in model membrane systems
journal, September 1993


Effect of Magnetic Field on the Fluorescence of Tetracene Crystals: Exciton Fission
journal, March 1969


Fission of singlet excitons into pairs of triplet excitons in tetracene crystals
journal, June 1969


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


Triplet exciton caging in two dimensions
journal, June 1976


Spectroscopic Approach to Energetics of Exciton Fission and Fusion in Tetracene Crystals
journal, May 1971


Heterofission of pentacene excited singlets in pentacene-doped tetracene crystals
journal, November 1971


Fission of a higher excited state generated by singlet exciton fusion in an anthracene crystal
journal, August 1992


Covalent Dimers of 1,3-Diphenylisobenzofuran for Singlet Fission: Synthesis and Electrochemistry
journal, December 2014


Excitation Localization/Delocalization Isomerism in a Strongly Coupled Covalent Dimer of 1,3-Diphenylisobenzofuran
journal, May 2016


Elektrochemische Erzeugung von Triplettzuständen
journal, January 1979


Diradical Character View of Singlet Fission
journal, December 2011


Exciton Fission and Fusion in Bis(tetracene) Molecules with Different Covalent Linker Structures
journal, November 2007

  • Müller, Astrid M.; Avlasevich, Yuri S.; Schoeller, Wolfgang W.
  • Journal of the American Chemical Society, Vol. 129, Issue 46, p. 14240-14250
  • https://doi.org/10.1021/ja073173y

Exciton dynamics in pentacene thin films studied by pump-probe spectroscopy
journal, July 1995


Temperature dependence of the triplet exciton yield in fission and fusion in tetracene
journal, August 1981


Classification of Spectra of Cata‐Condensed Hydrocarbons
journal, May 1949


Evidence for exciton fission and fusion in a covalently linked tetracene dimer
journal, April 2006


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


First-Principles Quantum Dynamics of Singlet Fission: Coherent versus Thermally Activated Mechanisms Governed by Molecular π Stacking
journal, August 2015


Mechanism of Singlet Fission in Thin Films of 1,3-Diphenylisobenzofuran
journal, May 2014


On singlet exciton fission in anthracene and tetracene at 77°K
journal, April 1973


Singlet exciton fission in pure and doped anthracene
journal, April 1979


Calculations of the Optical Spectra of Hydrocarbon Radical Cations Based on Koopmans' Theorem
journal, March 2007


Singlet Fission
journal, November 2010


Comments on exciton fission and electron spin resonance in tetracene single crystals
journal, October 1972


Fluorescence decay time measurements in tetracene crystals excited with synchrotron radiation
journal, October 1976


Autoxidation and Photooxidation of 1,3-Diphenylisobenzofuran: A Kinetic and Product Study
journal, July 1975


Seeking Small Molecules for Singlet Fission: A Heteroatom Substitution Strategy
journal, August 2014


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


Enabling singlet fission by controlling intramolecular charge transfer in π-stacked covalent terrylenediimide dimers
journal, August 2016


Resonant energy transfer of triplet excitons from pentacene to PbSe nanocrystals
journal, October 2014


Tuning the role of charge-transfer states in intramolecular singlet exciton fission through side-group engineering
journal, December 2016


Fission of Entangled Spins: An Electronic Structure Perspective
journal, November 2013


High-Yield Singlet Fission in a Zeaxanthin Aggregate Observed by Picosecond Resonance Raman Spectroscopy
journal, October 2010


Guidance for Mutual Disposition of Chromophores for Singlet Fission
journal, October 2015


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


Energy harvesting of non-emissive triplet excitons in tetracene by emissive PbS nanocrystals
journal, October 2014


Captodatively Stabilized Biradicaloids as Chromophores for Singlet Fission
journal, December 2014


Magnetic circular dichroism of aromatic molecules
journal, January 1984


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


Toward Designed Singlet Fission: Solution Photophysics of Two Indirectly Coupled Covalent Dimers of 1,3-Diphenylisobenzofuran
journal, November 2012


The Role of Chromophore Coupling in Singlet Fission
journal, January 2013


Detailed Balance Limit of Efficiency of p‐n Junction Solar Cells
journal, March 1961


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


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


The triplet state energies of rubrene and diphenylisobenzofuran
journal, August 1981


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


Structural Changes Accompanying Intramolecular Electron Transfer:  Focus on Twisted Intramolecular Charge-Transfer States and Structures
journal, October 2003


Rate constants of singlet exciton fission in a tetracene crystal determined from the rydmr spectral linewidth
journal, September 1978


Search for a Small Chromophore with Efficient Singlet Fission: Biradicaloid Heterocycles
journal, August 2012


Quantitative Intramolecular Singlet Fission in Bipentacenes
journal, July 2015


Excited state dynamics in solid and monomeric tetracene: The roles of superradiance and exciton fission
journal, October 2010


Configurational Interaction in Simple Molecular Orbital Theory
journal, November 1954


Works referencing / citing this record:

Feinabstimmung von intramolekularem resonantem Förster-Energietransfer und Aktivierung intramolekularer Singulettspaltung
journal, October 2018


Tuning Intramolecular Förster Resonance Energy Transfer and Activating Intramolecular Singlet Fission
journal, October 2018


Theoretical Studies of Singlet Fission: Searching for Materials and Exploring Mechanisms
journal, February 2018


Optimal arrangements of 1,3-diphenylisobenzofuran molecule pairs for fast singlet fission
journal, January 2019


Design of singlet fission chromophores with cyclic (alkyl)(amino) carbene building blocks
journal, June 2019