On the Importance of Chemical Precision in Organic Electronics: Fullerene Intercalation in Perfectly Alternating Conjugated Polymers

Jochen Vanderspikken, Zhen Liu, Xiaocui Wu, Omar Beckers, Stefania Moro, Tyler James Quill, Quan Liu, Arwin Goossens, Adam Marks, Karrie Weaver, Mouna Hamid, Bart Goderis, Erik Nies, Vincent Lemaur, David Beljonne, Alberto Salleo, Laurence Lutsen, Koen Vandewal, Bruno Van Mele, Giovanni Costantini*Niko Van den Brande*, Wouter Maes*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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Abstract

The true structure of alternating conjugated polymers—the state‐of‐the‐art materials for many organic electronics—often deviates from the idealized picture. Homocoupling defects are in fact inherent to the widely used cross‐coupling polymerization methods. Nevertheless, many polymers still perform excellently in the envisaged applications, which raises the question if one should really care about these imperfections. This article looks at the relevance of chemical precision (and lack thereof) in conjugated polymers covering the entire spectrum from the molecular scale, to the micro and mesostructure, up to the device level. The different types of polymerization errors for the alkoxylated variant of the benchmark (semi)crystalline polymer poly[2,5‐bis(3‐tetradecylthiophen‐2‐yl)thieno[3,2‐b]thiophene (PBTTT) are identified, visualized, and quantified and a general strategy to avoid homocoupling is introduced. Through a combination of experiments and supported by simulations, it is shown that these coupling defects hinder fullerene intercalation and limit device performance as compared to the homocoupling‐free analog. This clearly demonstrates that structural defects do matter and should be generally avoided, in particular when the geometrical regularity of the polymer is essential. These insights likely go beyond the specific PBTTT derivatives studied here and are of general relevance for the wider organic electronics field.
Original languageEnglish
Article number2309403
JournalAdvanced Functional Materials
Early online date10 Sept 2023
DOIs
Publication statusE-pub ahead of print - 10 Sept 2023

Keywords

  • Stille cross‐coupling
  • homocoupling
  • intermolecular charge‐transfer absorption
  • structural defect quantification
  • polymer:fullerene co‐crystals

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