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. 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:
-
[1];
[2]
- National Renewable Energy Lab. (NREL), Golden, CO (United States)
- Univ. of Colorado, Boulder, CO (United States); Academy of Sciences of the Czech Republic, Prague (Czech Republic)
- Publication Date:
- Research Org.:
- Univ. of Colorado, Boulder, CO (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1678685
- Grant/Contract Number:
- SC0007004
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Topics in Current Chemistry Collections
- Additional Journal Information:
- Journal Volume: 2017; Related Information: Physical Organic Chemistry of Quinodimethanes - book title; Journal ID: ISSN 2367-4067
- Publisher:
- Springer Nature
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 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:10.1007/978-3-319-93302-3_6.
Johnson, Justin C., & Michl, Josef. 1,3-Diphenylisobenzofuran: a Model Chromophore for Singlet Fission. United States. https://doi.org/10.1007/978-3-319-93302-3_6
Johnson, Justin C., and Michl, Josef. Mon .
"1,3-Diphenylisobenzofuran: a Model Chromophore for Singlet Fission". United States. https://doi.org/10.1007/978-3-319-93302-3_6. https://www.osti.gov/servlets/purl/1678685.
@article{osti_1678685,
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. 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 = {10.1007/978-3-319-93302-3_6},
journal = {Topics in Current Chemistry Collections},
number = ,
volume = 2017,
place = {United States},
year = {Mon Sep 11 00:00:00 EDT 2017},
month = {Mon Sep 11 00:00:00 EDT 2017}
}
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Figure 1: Singlet excitation (1) followed by SF (2). Reprinted with permission from reference 3. Copyright 2010 American Chemical Society.
Works referencing / citing this record:
Diabatization by Localization in the Framework of Configuration Interaction Based on Floating Occupation Molecular Orbitals (FOMO−CI)
journal, May 2019
- Accomasso, Davide; Persico, Maurizio; Granucci, Giovanni
- ChemPhotoChem, Vol. 3, Issue 9
Theoretical Studies of Singlet Fission: Searching for Materials and Exploring Mechanisms
journal, February 2018
- Japahuge, Achini; Zeng, Tao
- ChemPlusChem, Vol. 83, Issue 4
Tuning Intramolecular Förster Resonance Energy Transfer and Activating Intramolecular Singlet Fission
journal, October 2018
- Lavarda, Giulia; Zirzlmeier, Johannes; Gruber, Marco
- Angewandte Chemie International Edition, Vol. 57, Issue 50
Design of singlet fission chromophores with cyclic (alkyl)(amino) carbene building blocks
journal, June 2019
- Japahuge, Achini; Lee, Seunghoon; Choi, Cheol Ho
- The Journal of Chemical Physics, Vol. 150, Issue 23
Feinabstimmung von intramolekularem resonantem Förster-Energietransfer und Aktivierung intramolekularer Singulettspaltung
journal, October 2018
- Lavarda, Giulia; Zirzlmeier, Johannes; Gruber, Marco
- Angewandte Chemie, Vol. 130, Issue 50
Figures / Tables found in this record: