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Title: Singlet Fission via an Excimer-Like Intermediate in 3,6-Bis(thiophen-2-yl)diketopyrrolopyrrole Derivatives

Abstract

Singlet fission (SF) in polycrystalline thin films of four 3,6-bis(thiophen-2-yl)diketopyrrolopyrrole (TDPP) chromophores with methyl (Me), n-hexyl (C6), triethylene glycol (TEG), and 2-ethylhexyl (EH) substituents at the 2,5-positions is found to involve an intermediate excimer-like state. We report the four different substituents yield four distinct intermolecular packing geometries, resulting in variable intermolecular charge transfer (CT) interactions in the solid. SF from the excimer state of Me, C6, TEG, and EH takes place in τSF = 22, 336, 195, and 1200 ps, respectively, to give triplet yields of 200%, 110%, 110%, and 70%, respectively. The transient spectra of the excimer-like state and its energetic proximity to the lowest excited singlet state in these derivatives suggests that this state may be the multiexciton 1(T1T1) state that precedes formation of the uncorrelated triplet excitons. The excimer decay rates correlate well with the SF efficiencies and the degree of intermolecular donor–acceptor interactions resulting from π-stacking of the thiophene donor of one molecule with the DPP core acceptor in another molecule as observed in the crystal structures. Such interactions are found to also increase with the SF coupling energies, as calculated for each derivative. These structural and spectroscopic studies afford a better understanding of the electronicmore » interactions that enhance SF in chromophores having strong intra- and intermolecular CT character.« less

Authors:
 [1];  [2];  [2];  [2];  [2];  [2];  [2];  [2]
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  1. Energy Frontier Research Centers (EFRC) (United States). Argonne-Northwestern Solar Energy Research Center (ANSER); Northwestern Univ., Evanston, IL (United States). Inst. for Sustainability and Energy at Northwestern
  2. Energy Frontier Research Centers (EFRC) (United States). Argonne-Northwestern Solar Energy Research Center (ANSER); Northwestern Univ., Evanston, IL (United States). Inst. for Sustainability and Energy at Northwestern
Publication Date:
Research Org.:
Energy Frontier Research Centers (EFRC) (United States). Argonne-Northwestern Solar Energy Research Center (ANSER)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division; National Science Foundation (NSF); International Institute for Nanotechnology (IIN); Keck Foundation; State of Illinois
OSTI Identifier:
1388173
Grant/Contract Number:  
SC0001059; FG02-99ER14999; DGE-1324585
Resource Type:
Accepted Manuscript
Journal Name:
Journal of the American Chemical Society
Additional Journal Information:
Journal Volume: 138; Journal Issue: 36; Related Information: ANSER partners with Northwestern University (lead); Argonne National Laboratory; University of Chicago; University of Illinois, Urbana-Champaign; Yale University; Journal ID: ISSN 0002-7863
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; catalysis (homogeneous); catalysis (heterogeneous); solar (photovoltaic); solar (fuels); photosynthesis (natural and artificial); bio-inspired; hydrogen and fuel cells; electrodes - solar; defects; charge transport; spin dynamics; membrane; materials and chemistry by design; optics; synthesis (novel materials); synthesis (self-assembly); reaction products; crystal structure; oligomers; differential pulse voltammetry; quantum mechanics

Citation Formats

Mauck, Catherine M., Hartnett, Patrick E., Margulies, Eric A., Ma, Lin, Miller, Claire E., Schatz, George C., Marks, Tobin J., and Wasielewski, Michael R. Singlet Fission via an Excimer-Like Intermediate in 3,6-Bis(thiophen-2-yl)diketopyrrolopyrrole Derivatives. United States: N. p., 2016. Web. doi:10.1021/jacs.6b05627.
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Mauck, Catherine M., Hartnett, Patrick E., Margulies, Eric A., Ma, Lin, Miller, Claire E., Schatz, George C., Marks, Tobin J., & Wasielewski, Michael R. Singlet Fission via an Excimer-Like Intermediate in 3,6-Bis(thiophen-2-yl)diketopyrrolopyrrole Derivatives. United States. https://doi.org/10.1021/jacs.6b05627
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Mauck, Catherine M., Hartnett, Patrick E., Margulies, Eric A., Ma, Lin, Miller, Claire E., Schatz, George C., Marks, Tobin J., and Wasielewski, Michael R. Mon . "Singlet Fission via an Excimer-Like Intermediate in 3,6-Bis(thiophen-2-yl)diketopyrrolopyrrole Derivatives". United States. https://doi.org/10.1021/jacs.6b05627. https://www.osti.gov/servlets/purl/1388173.
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@article{osti_1388173,
title = {Singlet Fission via an Excimer-Like Intermediate in 3,6-Bis(thiophen-2-yl)diketopyrrolopyrrole Derivatives},
author = {Mauck, Catherine M. and Hartnett, Patrick E. and Margulies, Eric A. and Ma, Lin and Miller, Claire E. and Schatz, George C. and Marks, Tobin J. and Wasielewski, Michael R.},
abstractNote = {Singlet fission (SF) in polycrystalline thin films of four 3,6-bis(thiophen-2-yl)diketopyrrolopyrrole (TDPP) chromophores with methyl (Me), n-hexyl (C6), triethylene glycol (TEG), and 2-ethylhexyl (EH) substituents at the 2,5-positions is found to involve an intermediate excimer-like state. We report the four different substituents yield four distinct intermolecular packing geometries, resulting in variable intermolecular charge transfer (CT) interactions in the solid. SF from the excimer state of Me, C6, TEG, and EH takes place in τSF = 22, 336, 195, and 1200 ps, respectively, to give triplet yields of 200%, 110%, 110%, and 70%, respectively. The transient spectra of the excimer-like state and its energetic proximity to the lowest excited singlet state in these derivatives suggests that this state may be the multiexciton 1(T1T1) state that precedes formation of the uncorrelated triplet excitons. The excimer decay rates correlate well with the SF efficiencies and the degree of intermolecular donor–acceptor interactions resulting from π-stacking of the thiophene donor of one molecule with the DPP core acceptor in another molecule as observed in the crystal structures. Such interactions are found to also increase with the SF coupling energies, as calculated for each derivative. These structural and spectroscopic studies afford a better understanding of the electronic interactions that enhance SF in chromophores having strong intra- and intermolecular CT character.},
doi = {10.1021/jacs.6b05627},
journal = {Journal of the American Chemical Society},
number = 36,
volume = 138,
place = {United States},
year = {Mon Aug 22 00:00:00 EDT 2016},
month = {Mon Aug 22 00:00:00 EDT 2016}
}
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https://doi.org/10.1021/jacs.6b05627
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Figures / Tables:

Scheme 1 Scheme 1: Synthesis and nomenclature for the TDPP series investigated here
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