Crystallization and Organic Field‐Effect Transistor Performance of a Hydrogen‐Bonded Quaterthiophene. Issue 45 (16th July 2020)

• Record Type: Journal Article
• Authors: Gebers, Jan; Özen, Bilal; Hartmann, Lucia; Schaer, Michel; Suàrez, Stéphane; Bugnon, Philippe; Scopelliti, Rosario; Steinrück, Hans‐Georg; Konovalov, Oleg; Magerl, Andreas; Brinkmann, Martin; Petraglia, Riccardo; de Silva, Piotr; Corminboeuf, Clémence; Frauenrath, Holger
• Is Part Of: Chemistry. Volume 26:Issue 45(2020)
• Page Start: 10265
• Page End: 10275
• Publication Date: 2020-07-16
• Subjects: hydrogen bonds -- oligothiophenes -- organic field-effect transistors -- organic semiconductors -- structure–activity relationships; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201904562
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Crystalline thin films of π‐conjugated molecules are relevant as the active layers in organic electronic devices. Therefore, materials with enhanced control over the supramolecular arrangement, crystallinity, and thin‐film morphology are desirable. Herein, it is reported that hydrogen‐bonded substituents serve as additional structure‐directing elements that positively affect crystallization, thin‐film morphology, and device performance of p‐type organic semiconductors. It is observed that a quaterthiophene diacetamide exhibits a denser packing than that of other quaterthiophenes in the single‐crystal structure and, as a result, displays enhanced intermolecular electronic interactions. This feature was preserved in crystalline thin films that exhibited a layer‐by‐layer morphology, with large domain sizes and high internal order. As a result, organic field‐effect transistors of these polycrystalline thin films showed mobilities in the range of the best mobility values reported for single‐crystalline quaterthiophenes. The use of hydrogen‐bonded groups may, thus, provide an avenue for organic semiconducting materials with improved morphology and performance. Abstract : Engineering on the side : Hydrogen‐bonded substituents serve as an additional structure‐directing element to control the packing of quaterthiophene, with larger π overlap, improved crystalline order, and larger domain sizes than that of related molecules without hydrogen‐bonded substituents. These factors lead to an improved performance of the thin films in organic field‐effect transistors similar to that of single crystals of related quaterthiophene derivatives.