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:
-
- National Renewable Energy Lab. (NREL), Golden, CO (United States)
- 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 = {Mon Sep 11 00:00:00 EDT 2017},
month = {Mon Sep 11 00:00:00 EDT 2017}
}
Web of Science
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