Effects of Crystal Morphology on Singlet Exciton Fission in Diketopyrrolopyrrole Thin Films

The Journal of Physical Chemistry. B
Patrick E HartnettMichael R Wasielewski

Abstract

Singlet exciton fission (SF) is a promising strategy for increasing photovoltaic efficiency, but in order for SF to be useful in solar cells, it should take place in a chromophore that is air-stable, highly absorptive, solution processable, and inexpensive. Unlike many SF chromophores, diketopyrrolopyrrole (DPP) conforms to these criteria, and here we investigate SF in DPP for the first time. SF yields in thin films of DPP derivatives, which are widely used in organic electronics and photovoltaics, are shown to depend critically on crystal morphology. Time-resolved spectroscopy of three DPP derivatives with phenyl (3,6-diphenylpyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione, PhDPP), thienyl (3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione, TDPP), and phenylthienyl (3,6-di(5-phenylthiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione, PhTDPP) aromatic substituents in 100-200 nm thin films reveals that efficient SF occurs only in TDPP and PhTDPP (τSF = 220 ± 20 ps), despite the fact that SF is most exoergic in PhDPP. This result correlates well with the greater degree of π-overlap and closer π-stacking in TDPP (3.50 Å) and PhTDPP (3.59 Å) relative to PhDPP (3.90 Å) and demonstrates that SF in DPP is highly sensitive to the elec...Continue Reading

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Citations

May 12, 2016·Journal of the American Chemical Society·You-Dan ZhangHao-Li Zhang
Jun 14, 2016·The Journal of Physical Chemistry. a·Jasper D CookNiels H Damrauer
Aug 23, 2016·Journal of the American Chemical Society·Catherine M MauckMichael R Wasielewski
Dec 16, 2016·Journal of the American Chemical Society·Eric A MarguliesMichael R Wasielewski
Dec 28, 2016·Journal of the American Chemical Society·Patrick E HartnettMichael R Wasielewski
Jan 24, 2017·The Journal of Physical Chemistry Letters·Tushita MukhopadhyaySatish Patil
May 19, 2017·Nature Communications·Bettina S BaselDirk M Guldi
Jan 13, 2018·Chemistry : a European Journal·Constantin HetzerRik R Tykwinski
Aug 10, 2018·Chemical Science·Ryan D PensackGregory D Scholes
Jan 18, 2019·Nature·Benjamin D RavetzLuis M Campos
Nov 16, 2019·Nanoscale·Diana-Paola MedinaTomás Torres
Apr 25, 2019·Chemical Science·Bettina Sabine BaselRik R Tykwinski
Dec 18, 2020·ChemPlusChem·David RaisJosef Michl
Jan 27, 2021·Chemical Society Reviews·Tobias UllrichDirk M Guldi
Apr 23, 2021·Physical Chemistry Chemical Physics : PCCP·Siobhan J BradleyKenneth P Ghiggino
Jul 29, 2021·The Journal of Physical Chemistry Letters·Maria Fumanal, Clémence Corminboeuf
Nov 8, 2017·The Journal of Physical Chemistry Letters·Christopher GriecoJohn B Asbury
Nov 4, 2020·The Journal of Physical Chemistry. a·Kaia R ParentiLuis M Campos
Dec 15, 2017·Journal of the American Chemical Society·Aaron K LeSean T Roberts
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Dec 15, 2016·Journal of the American Chemical Society·Christopher GriecoJohn B Asbury
Oct 30, 2018·Journal of the American Chemical Society·Youn Jue BaeMichael R Wasielewski
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Nov 23, 2017·Journal of the American Chemical Society·Steven LukmanAndrew J Musser
Oct 7, 2020·Journal of the American Chemical Society·Carolyn E RamirezMichael R Wasielewski
Oct 13, 2020·Journal of the American Chemical Society·Long WangHongbing Fu
Nov 12, 2020·Journal of the American Chemical Society·Kealan J FallonLuis M Campos
May 3, 2019·The Journal of Physical Chemistry. C, Nanomaterials and Interfaces·Robin E M WillemsRené A J Janssen

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