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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, 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 =

Authors:
 [1]; ORCiD logo [2]; ORCiD logo [3]
  1. Univ. of Colorado, Boulder, CO (United States). Dept. of Chemistry and Biochemistry
  2. 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
  3. National Renewable Energy Lab. (NREL), Golden, CO (United States)
Publication Date:
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. https://doi.org/10.1021/acs.jpca.7b07362.
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
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.
@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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Cited by: 8 works
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    Works referencing / citing this record:

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