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

Mauck, Catherine M.; Hartnett, Patrick E.; Margulies, Eric A.; Ma, Lin; Miller, Claire E.; Schatz, George C.; Marks, Tobin J.; Wasielewski, Michael R.

doi:10.1021/jacs.6b05627

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

Journal Article · Mon Aug 22 00:00:00 EDT 2016 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.6b05627· OSTI ID:1388173

Mauck, Catherine M. ^[1]; Hartnett, Patrick E. ^[2]; Margulies, Eric A. ^[2]; Ma, Lin ^[2]; Miller, Claire E. ^[2]; Schatz, George C. ^[2]; Marks, Tobin J. ^[2]; Wasielewski, Michael R. ^[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
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

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 τ_SF = 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.

View Accepted Manuscript (DOE)

Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Argonne-Northwestern Solar Energy Research Center (ANSER)

Sponsoring Organization:: International Institute for Nanotechnology (IIN); Keck Foundation; National Science Foundation (NSF); State of Illinois; USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division

Grant/Contract Number:: FG02-99ER14999; SC0001059

OSTI ID:: 1388173

Alternate ID(s):: OSTI ID: 1376256

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 36 Vol. 138; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Charge-Transfer Character in a Covalent Diketopyrrolopyrrole Dimer: Implications for Singlet Fission Mauck, Catherine M.; Bae, Youn Jue; Chen, Michelle ChemPhotoChem, Vol. 2, Issue 3 https://doi.org/10.1002/cptc.201700135	journal	October 2017
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Substituent effects on energetics and crystal morphology modulate singlet fission in 9,10-bis(phenylethynyl)anthracenes Bae, Youn Jue; Christensen, Joseph A.; Kang, Gyeongwon The Journal of Chemical Physics, Vol. 151, Issue 4 https://doi.org/10.1063/1.5110411	journal	July 2019
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Understanding the Excited State Photophysics of Pyrrolopyrrole-Dione Isomers and Derivatives Using Time-Dependence Density Functional Theory Tam, Teck Lip Dexter; Lin, Ting Ting; Lukman, Steven Journal of Molecular and Engineering Materials, Vol. 05, Issue 03 https://doi.org/10.1142/s2251237317500095	journal	September 2017
Davydov splitting and singlet fission in excitonically coupled pentacene dimers Basel, Bettina Sabine; Hetzer, Constantin; Zirzlmeier, Johannes Cambridge : RSC https://doi.org/10.34657/5836	null	January 2019
The hierarchical and perturbative forms of stochastic Schrödinger equations and their applications to carrier dynamics in organic materials Wang, Yuchen; Ke, Yaling; Zhao, Yi arXiv https://doi.org/10.48550/arxiv.1805.07539	text	January 2018
Enhanced Delayed Fluorescence in Tetracene Crystals by Strong Light-Matter Coupling Berghuis, Matthijs; Halpin, Alexei; Le-Van, Quynh arXiv https://doi.org/10.48550/arxiv.1907.01961	text	January 2019

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
bio-inspired
catalysis (heterogeneous)
catalysis (homogeneous)
charge transport
crystal structure
defects
differential pulse voltammetry
electrodes - solar
hydrogen and fuel cells
materials and chemistry by design
membrane
oligomers
optics
photosynthesis (natural and artificial)
quantum mechanics
reaction products
solar (fuels)
solar (photovoltaic)
spin dynamics
synthesis (novel materials)
synthesis (self-assembly)

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

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