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CC BY-NC-ND 4.0 · Organic Materials 2020; 02(03): 229-234
DOI: 10.1055/s-0040-1714283
Focus Issue: Curved Organic π-Systems
Short Communication

Bowl-Shaped Naphthalimide-Annulated Corannulene as Nonfullerene Acceptor in Organic Solar Cells

Kaan Menekse‡   ‡
a   Center for Nanosystems Chemistry, Universität Würzburg, Theodor-Boveri-Weg, 97074 Würzburg, Germany
,
Rebecca Renner‡   ‡
b   Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
,
Bernhard Mahlmeister
a   Center for Nanosystems Chemistry, Universität Würzburg, Theodor-Boveri-Weg, 97074 Würzburg, Germany
,
Matthias Stolte
a   Center for Nanosystems Chemistry, Universität Würzburg, Theodor-Boveri-Weg, 97074 Würzburg, Germany
b   Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
,
Frank Würthner 
a   Center for Nanosystems Chemistry, Universität Würzburg, Theodor-Boveri-Weg, 97074 Würzburg, Germany
b   Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
› Institutsangaben Funding Information We are grateful for financial support from the Deutsche Forschungsgemeinschaft (Grant Wu 317/20-1) as well as the Bavarian Research Program “Solar Technologies Go Hybrid”.
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Abstract

An electron-poor bowl-shaped naphthalimide-annulated corannulene with branched alkyl residues in the imide position was synthesized by a palladium-catalyzed cross-coupling annulation sequence. This dipolar compound exhibits strong absorption in the visible range along with a low-lying LUMO level at –3.85 eV, enabling n-type charge transport in organic thin-film transistors. Furthermore, we processed inverted bulk-heterojunction solar cells in combination with the two donor polymers PCE–10 and PM6 to achieve open-circuit voltages up to 1.04 V. By using a blend of the self-assembled naphthalimide-annulated corannulene and PCE–10, we were able to obtain a power conversion efficiency of up to 2.1%, which is to the best of our knowledge the highest reported value for a corannulene-based organic solar cell to date.

Key words

corannulene - curved π-systems - bulk-heterojunction solar cells - nonfullerene acceptors - aggregation

Supporting Information

Supporting information for this article is available online at http://doi.org/10.1055/s-0040-1714283.


‡ Kaan Menekse and Rebecca Renner contributed equally to this work.


Supplementary Material



Publikationsverlauf

Eingereicht: 25. Mai 2020

Angenommen: 12. Juni 2020

Artikel online veröffentlicht:
09. September 2020

© 2020. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/).

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Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Ma Z, Winands T, Liang N, Meng D, Jiang W, Doltsinis NL, Wang Z. Sci. China Chem. 2020; 63: 208
    CrossrefPubMedSuche in Google Scholar
  • 2 Wang X.-Y, Yao X, Müllen K. Sci. China Chem. 2019; 62: 1099
    CrossrefPubMedSuche in Google Scholar
  • 3 Wu Y.-T, Siegel JS. Chem. Rev. 2006; 106: 4843
    CrossrefPubMedSuche in Google Scholar
  • 4 Duan C, Zango G, García Iglesias M, Colberts FJ.M, Wienk MM, Martínez-Díaz MV, Janssen RA.J, Torres T. Angew. Chem. Int. Ed. 2017; 56: 148
    CrossrefPubMedSuche in Google Scholar
  • 5 Magiera KM, Aryal V, Chalifoux WA. Org. Biomol. Chem. 2020; 18: 2372
    CrossrefPubMedSuche in Google Scholar
  • 6 Meng D, Liu G, Xiao C, Shi Y, Zhang L, Jiang L, Baldridge KK, Li Y, Siegel JS, Wang Z. J. Am. Chem. Soc. 2019; 141: 5402
    CrossrefPubMedSuche in Google Scholar
  • 7 Huang X, Hu M, Zhao X, Li C, Yuan Z, Liu X, Cai C, Zhang Y, Hu Y, Chen Y. Org. Lett. 2019; 21: 3382
    CrossrefPubMedSuche in Google Scholar
  • 8 Luo Z, Liu T, Cheng W, Wu K, Xie D, Huo L, Sun Y, Yang C. J. Mater. Chem. C 2018; 6: 1136
    CrossrefPubMedSuche in Google Scholar
  • 9 Hendsbee AD, Sun J.-P, Law WK, Yan H, Hill IG, Spasyuk DM, Welch GC. Chem. Mater. 2016; 28: 7098
    CrossrefPubMedSuche in Google Scholar
  • 10 Zhong Y, Trinh MT, Chen R, Purdum GE, Khlyabich PP, Sezen M, Oh S, Zhu H, Fowler B, Zhang B, Wang W, Nam CY, Sfeir MY, Black CT, Steigerwald ML, Loo YL, Ng F, Zhu XY, Nuckolls C. Nat. Commun. 2015; 6: 8242
    CrossrefPubMedSuche in Google Scholar
  • 11 Huang T, Chen H, Feng J, Zhang A, Jiang W, He F, Wang Z. ACS Mater. Lett. 2019; 1: 404
    CrossrefPubMedSuche in Google Scholar
  • 12 Verreet B, Rand BP, Cheyns D, Hadipour A, Aernouts T, Heremans P, Medina A, Claessens CG, Torres T. Adv. Energy Mater. 2011; 1: 565
    CrossrefPubMedSuche in Google Scholar
  • 13 Barth WE, Lawton RG. J. Am. Chem. Soc. 1966; 88: 380
    CrossrefPubMedSuche in Google Scholar
  • 14 Nestoros E, Stuparu MC. Chem. Commun. 2018; 54: 6503
    CrossrefPubMedSuche in Google Scholar
  • 15 Chen R, Lu R.-Q, Shi K, Wu F, Fang H.-X, Niu Z.-X, Yan X.-Y, Luo M, Wang X.-C, Yang C.-Y, Wang X.-Y, Xu B, Xia H, Pei J, Cao X.-Y. Chem. Commun. 2015; 51: 13768
    CrossrefPubMedSuche in Google Scholar
  • 16 Shi K, Lei T, Wang X.-Y, Wang J.-Y, Pei J. Chem. Sci. 2014; 5: 1041
    CrossrefPubMedSuche in Google Scholar
  • 17 Lu R.-Q, Zhou Y.-N, Yan X.-Y, Shi K, Zheng Y.-Q, Luo M, Wang X.-C, Pei J, Xia H, Zoppi L, Baldridge KK, Siegel JS, Cao X.-Y. Chem. Commun. 2015; 51: 1681
    CrossrefPubMedSuche in Google Scholar
  • 18 Mack J, Vogel P, Jones D, Kaval N, Sutton A. Org. Biomol. Chem. 2007; 5: 2448
    CrossrefPubMedSuche in Google Scholar
  • 19 Valenti G, Bruno C, Rapino S, Fiorani A, Jackson EA, Scott LT, Paolucci F, Marcaccio M. J. Phys. Chem. C 2010; 114: 19467
    CrossrefPubMedSuche in Google Scholar
  • 20 Li J, Terec A, Wang Y, Joshi H, Lu Y, Sun H, Stuparu MC. J. Am. Chem. Soc. 2017; 139: 3089
    CrossrefPubMedSuche in Google Scholar
  • 21 Anthony JE. Chem. Mater. 2011; 23: 583
    CrossrefPubMedSuche in Google Scholar
  • 22 Chen R, Lu R.-Q, Shi P.-C, Cao X.-Y. Chin. Chem. Lett. 2016; 27: 1175
    CrossrefPubMedSuche in Google Scholar
  • 23 Rajeshkumar V, Marc C, Fichou D, Stuparu MC. Synlett 2016; 27: 2101
    Thieme ConnectPubMedSuche in Google Scholar
  • 24 Deng Y, Xu B, Castro E, Fernandez-Delgado O, Echegoyen L, Baldridge KK, Siegel JS. Eur. J. Org. Chem. 2017; 29: 4338
    CrossrefPubMedSuche in Google Scholar
  • 25 Lu RQ, Zheng YQ, Zhou YN, Yan XY, Lei T, Shi K, Zhou Y, Pei J, Zoppi L, Baldridge KK, Siegel JS, Cao XY. J. Mater. Chem. A 2014; 2: 20515
    CrossrefPubMedSuche in Google Scholar
  • 26 Shoyama K, Schmidt D, Mahl M, Würthner F. Org. Lett. 2017; 19: 5328
    CrossrefPubMedSuche in Google Scholar
  • 27 Renner R, Stolte M, Würthner F. ChemistryOpen 2019; 9: 32
    CrossrefPubMedSuche in Google Scholar
  • 28 Shoyama K, Würthner F. J. Am. Chem. Soc. 2019; 141: 13008
    CrossrefPubMedSuche in Google Scholar
  • 29 Gershberg J, Fennel F, Rehm TH, Lochbrunner S, Würthner F. Chem. Sci. 2016; 7: 1729
    CrossrefPubMedSuche in Google Scholar
  • 30 Cardona CM, Li W, Kaifer AE, Stockdale D, Bazan GC. Adv. Mater. 2011; 23: 2367
    CrossrefPubMedSuche in Google Scholar
  • 31 Organic solar cells were prepared by cleaning ITO substrates (Soluxx GmbH) with acetone (VWR, semiconductor grade), detergent, deionized water, and isopropanol (VWR, semiconductor grade) for 15 min each, followed by an ozone/UV treatment for 30 min. The ZnO layer was deposited by spin-coating ZnO nanoparticles on top of the substrates (3000 rpm, 30 s) followed by an annealing step (200 °C, 1 h). The donor–acceptor blends were prepared by stirring a 1:1 mixture with a total concentration of 15 mg mL−1 of donor (PCE-10 obtained from 1-Material Inc.; PM6 obtained from Brilliant Matters Inc.) and 4 in chlorobenzene for 3 h at room temperature under inert conditions followed by spin-coating at 1000 rpm for 60 s (M. Braun Inertgas-Systeme GmbH, UNIlab Pro, c(O2) < 1 ppm, c(H2O) < 1 ppm). The substrates were placed in the evaporation system (OPTIvap-XL, Creaphys GmbH) and MoO3 d = 10 nm, r = 0.1 Å s−1, p < 10−6 mbar, rotation = 10 rpm) and aluminum (d = 100 nm, r = 1–2 Å s−1, p < 10−6 mbar) were deposited on top of the active layer to obtain the inverted BHJ organic solar cells. The device area was 7.1 mm2. J–V characteristics were measured after calibration with a standard silicon solar cell with a KG filter (ISE Freiburg) under an AM1.5G Oriel Sol3ATM Class AAA solar simulator (Newport® ) by a parameter analyzer (Botest Systems GmbH). EQE measurements were carried out with a quantum efficiency/IPCE measurement kit (Newport®) by using a 300 W Xe lamp and a Cornerstone monochromator with a Merlin lock-in amplifier for detection. Thin-film UV/Vis spectra were measured on a Jasco V770 spectrometer using an integration sphere. AFM images were obtained by an NT–MDT Next Solver system in semi-contact mode by using a SCOUT 350 RAI (Nu Nano Ltd) silicon cantilever (spring constant = 42 N m−1 ; resonance frequency = 350 kHz).The high-resolution AFM image was measured at a AXS Multimode Nanoscope IV instrument in the tapping mode using a silicon cantilever from Olympus (OMCL-AC160TS) with a spring constant of 42 N m−1 and a resonance frequency of 300 kHz
    PubMed
  • 32 Organic thin film transistors were fabricated on wafer substrates based on Si/SiO2(100 nm)/octadecyltriethoxysilane (OTES) with a capacitance of 32.4 nF cm−2, which were rinsed prior to use with toluene (p.a. grade, VWR chemicals), acetone, and isopropanol (semiconductor grade, VLSI PURANAL™, Aldrich® Chemistry), successively. After drying under nitrogen flow, the substrates were placed into a nitrogen-filled glovebox (M. Braun Inertgas-Systeme GmbH, UNIlab Pro, c(O2) < 1 ppm, c(H2O) < 1 ppm) and a freshly prepared solution of 4 (5 mg mL−1 in chloroform) was spin-coated on top of the substrate (1000 rpm, 60 s) followed by an annealing step (100 °C, 5 Min). The substrates were placed into an evaporation system (OPTIvap-XL, Creaphys GmbH) and gold was deposited on top of the organic layer through a shadow mask (d = 30 nm, r = 0.2 Å s−1, p < 10−6 mbar). The resulting transfer and output characteristics were measured under inert conditions with an Agilent 4055C parameter analyzer and a Cascade EPS150 probe station (W = 1000 μm, L = 20 μm)
    PubMed
  • 33 Würthner F, Meerholz K. Chemistry 2010; 16: 9366
    CrossrefPubMedSuche in Google Scholar