Slip-stacked perylenediimides as an alternative strategy for high efficiency nonfullerene acceptors in organic photovoltaics

Patrick E. Hartnett, Amod Timalsina, H. S S Ramakrishna Matte, Nanjia Zhou, Xugang Guo, Wei Zhao, Antonio Facchetti, Robert P. H. Chang, Mark C Hersam, Michael R Wasielewski, Tobin J Marks

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Abstract

Perylenediimide (PDI)-based acceptors offer a potential replacement for fullerenes in bulk-heterojunction (BHJ) organic photovoltaic cells (OPVs). The most promising efforts have focused on creating twisted PDI dimers to disrupt aggregation and thereby suppress excimer formation. Here, we present an alternative strategy for developing high-performance OPVs based on PDI acceptors that promote slip-stacking in the solid state, thus preventing the coupling necessary for rapid excimer formation. This packing structure is accomplished by substitution at the PDI 2,5,8,11-positions ("headland positions"). Using this design principle, three PDI acceptors, N,N-bis(n-octyl)-2,5,8,11-tetra(n-hexyl)-PDI (Hexyl-PDI), N,N-bis(n-octyl)-2,5,8,11-tetraphenethyl-PDI (Phenethyl-PDI), and N,N-bis(n-octyl)-2,5,8,11-tetraphenyl-PDI (Phenyl-PDI), were synthesized, and their molecular and electronic structures were characterized. They were then blended with the donor polymer PBTI3T, and inverted OPVs of the structure ITO/ZnO/Active Layer/MoO3/Ag were fabricated and characterized. Of these, 1:1 PBTI3T:Phenyl-PDI proved to have the best performance with Jsc = 6.56 mA/cm2, Voc = 1.024 V, FF = 54.59%, and power conversion efficiency (PCE) = 3.67%. Devices fabricated with Phenethyl-PDI and Hexyl-PDI have significantly lower performance. The thin film morphology and the electronic and photophysical properties of the three materials are examined, and although all three materials undergo efficient charge separation, PBTI3T:Phenyl-PDI is found to have the deepest LUMO, intermediate crystallinity, and the most well-mixed domains. This minimizes geminate recombination in Phenyl-PDI OPVs and affords the highest PCE. Thus, slip-stacked PDI strategies represent a promising approach to fullerene replacements in BHJ OPVs.

Original languageEnglish
Pages (from-to)16345-16356
Number of pages12
JournalJournal of the American Chemical Society
Volume136
Issue number46
DOIs
Publication statusPublished - Nov 19 2014

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Fullerenes
Conversion efficiency
Heterojunctions
Photovoltaic cells
Dimers
Molecular structure
Electronic structure
Substitution reactions
Agglomeration
Thin films
Polymers
perylenediimide
Molecular Structure
Genetic Recombination

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Slip-stacked perylenediimides as an alternative strategy for high efficiency nonfullerene acceptors in organic photovoltaics. / Hartnett, Patrick E.; Timalsina, Amod; Matte, H. S S Ramakrishna; Zhou, Nanjia; Guo, Xugang; Zhao, Wei; Facchetti, Antonio; Chang, Robert P. H.; Hersam, Mark C; Wasielewski, Michael R; Marks, Tobin J.

In: Journal of the American Chemical Society, Vol. 136, No. 46, 19.11.2014, p. 16345-16356.

Research output: Contribution to journalArticle

Hartnett, Patrick E. ; Timalsina, Amod ; Matte, H. S S Ramakrishna ; Zhou, Nanjia ; Guo, Xugang ; Zhao, Wei ; Facchetti, Antonio ; Chang, Robert P. H. ; Hersam, Mark C ; Wasielewski, Michael R ; Marks, Tobin J. / Slip-stacked perylenediimides as an alternative strategy for high efficiency nonfullerene acceptors in organic photovoltaics. In: Journal of the American Chemical Society. 2014 ; Vol. 136, No. 46. pp. 16345-16356.
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AU - Zhou, Nanjia

AU - Guo, Xugang

AU - Zhao, Wei

AU - Facchetti, Antonio

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AU - Hersam, Mark C

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N2 - Perylenediimide (PDI)-based acceptors offer a potential replacement for fullerenes in bulk-heterojunction (BHJ) organic photovoltaic cells (OPVs). The most promising efforts have focused on creating twisted PDI dimers to disrupt aggregation and thereby suppress excimer formation. Here, we present an alternative strategy for developing high-performance OPVs based on PDI acceptors that promote slip-stacking in the solid state, thus preventing the coupling necessary for rapid excimer formation. This packing structure is accomplished by substitution at the PDI 2,5,8,11-positions ("headland positions"). Using this design principle, three PDI acceptors, N,N-bis(n-octyl)-2,5,8,11-tetra(n-hexyl)-PDI (Hexyl-PDI), N,N-bis(n-octyl)-2,5,8,11-tetraphenethyl-PDI (Phenethyl-PDI), and N,N-bis(n-octyl)-2,5,8,11-tetraphenyl-PDI (Phenyl-PDI), were synthesized, and their molecular and electronic structures were characterized. They were then blended with the donor polymer PBTI3T, and inverted OPVs of the structure ITO/ZnO/Active Layer/MoO3/Ag were fabricated and characterized. Of these, 1:1 PBTI3T:Phenyl-PDI proved to have the best performance with Jsc = 6.56 mA/cm2, Voc = 1.024 V, FF = 54.59%, and power conversion efficiency (PCE) = 3.67%. Devices fabricated with Phenethyl-PDI and Hexyl-PDI have significantly lower performance. The thin film morphology and the electronic and photophysical properties of the three materials are examined, and although all three materials undergo efficient charge separation, PBTI3T:Phenyl-PDI is found to have the deepest LUMO, intermediate crystallinity, and the most well-mixed domains. This minimizes geminate recombination in Phenyl-PDI OPVs and affords the highest PCE. Thus, slip-stacked PDI strategies represent a promising approach to fullerene replacements in BHJ OPVs.

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