The effect of side-chain length on the microstructure and processing window of zone-cast naphthalene-based bispentalenes

Goetz, Katelyn P.; Sekine, Kohei; Paulus, Fabian; Zhong, Yu; Roth, Daniel; Becker‐Koch, David; Hofstetter, Yvonne J.; Michel, Elena; Reichert, Lisa; Röminger, Frank; Rudolph, Matthias; Huettner, Sven; Vaynzof, Yana; Herzig, Eva M.; Hashmi, A. Stephen K.; Zaumseil, Jana

doi:10.1039/c9tc04470a

Cited by 14 publications

(14 citation statements)

References 46 publications

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“…Normally, multiple solvents with the different boiling points need suitable shearing speed, solution concentration, substrate temperature, and even suitable organic materials for achieving uniform and dense organic channel. [80,81] Janneck et al proposed a predictive model at the different solvent evaporation rates in meniscus-guided coating techniques. [82] They also studied the effects of solvents and surface treatments on evaporation and zone-casting technique using C8-BTBT as the active material.…”

Section: Blade-coatingmentioning

confidence: 99%

Structures, Properties, and Device Applications for [1]Benzothieno[3,2‐b]Benzothiophene Derivatives

Xie

Liu

Sun

et al. 2022

Adv Funct Materials

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1]benzothieno[3,2-b]benzothiophene (BTBT), with two benzene rings as the outermost rings, is referred to as diacene-fused ladder-type π-conjugated thienothiophenes. During the last three decades, derivatives based on BTBT core have been extensively studied due to their tremendous application prospects in organic field-effect transistors (OFETs) and organic optoelectronic devices. In order to further advance the development of organic electronics, new materials are constantly being synthesized and new methods are constantly evolving. This review mainly focuses on the crystal and electronic structures of BTBT derivatives, the soluble and thermal properties, the fabrication methods, as well as the strategies for performance improvement and optoelectronic applications including OFETs, photodetectors, synaptic devices, and organic light-emitting transistors. As one of the most promising organic materials, the insight into BTBT-based molecules will accelerate their potential application and provide important reference value for the development toward commercialized and industrialized organic semiconducting products.

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Section: Blade-coatingmentioning

confidence: 99%

Structures, Properties, and Device Applications for [1]Benzothieno[3,2‐b]Benzothiophene Derivatives

Xie

Liu

Sun

et al. 2022

Adv Funct Materials

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“…These first results demonstrate that the bispentalene core is highly suitable for transistor applications. Further investigations concentrated on the effect of the alkyl side chain (which was installed for solubility reasons) of 99 on the microstructure and processing of the devices . Whereas the side-chain lengths in many semiconducting systems have a strong relationship to their optoelectronic properties, these results indicate surprisingly that the microstructure and order of the zone-cast films are the strongest factors influencing the charge transport.…”

Section: Extended Anellated Aromatic Systemsmentioning

confidence: 99%

Homogeneous and Heterogeneous Gold Catalysis for Materials Science

et al. 2020

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Often stoichiometric amounts of gold find use in materials science; occasionally gold is even used as a support. This review discusses the contributions of gold catalysis, both homogeneous and heterogeneous, to the field of materials science. One topic is the synthesis of polymers, including nanowires and polyesters, the postcyclization of polymers, polymerization by cyclopropanation, and gold-catalyzed radical polymerization reactions. Other topics are dyes, phosphonium salts, and a wide range of extended conjugated π-systems, the latter ranging from acenes, pentalene derivatives, and different heterocyclic π-systems to fascinating applications in the synthesis of helical anellated aromatic molecules. The existing contributions clearly demonstrate the potential of gold catalysis for significant future impulses for the field of materials science.

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“…Because devices such as organic field effect transistors are usually designed to work with charge carrier transport parallel to the substrate’s surface, ,, the establishment and ability to carefully control the molecular orientation are of crucial importance. Techniques such as inkjet printing and zone casting are promising in the aim to achieve this order along a certain axis to improve device performance. ,, We chose a zone-casting technique to fabricate a sample with a preferred direction on the substrate’s surface as explained in detail in the Methods section. From the AFM studies (Figure e,f), we see that large areas of crystallites with molecularly flat terraces are formed.…”

Section: Resultsmentioning

confidence: 99%

Deposition-Dependent Morphology and Infrared Vibrational Spectra of Brominated Tetraazaperopyrene Layers

et al. 2019

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A detailed infrared spectroscopic characterizationsupported by atomic force microscopyof core brominated tetraazaperopyrene (TAPP-Br) layers in terms of molecular orientation and stability against electron irradiation is presented. The anisotropy and the average molecular orientation of TAPP-Br molecules in optoelectronic device-relevant thin films (with ca. 20 nm thickness), grown by thermal evaporation under ultrahigh vacuum conditions and in a zone-cast sample, were established. To this end, the tensor components of the dielectric function were determined on the basis of spectra of a pellet sample and of a variety of polarization-dependent spectra of layers. Supported by density functional theory, the experimentally derived tensor components were related to dipoles of selected vibrational modes in the anisotropic TAPP-Br molecule and so to the average molecular orientation in the polycrystalline layers. Additionally, electron beam damage for energies ranging from ten to hundreds of electron volts was studied in order to obtain the threshold energy below which scanning electron microscopy can be carried out in a nondestructive way.

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The effect of side-chain length on the microstructure and processing window of zone-cast naphthalene-based bispentalenes

Abstract: The solubilizing side-groups of solution-processable π-conjugated organic semiconductors affect both the crystal structure and microstructure of the respective thin films and thus charge-carrier mobility in devices.

Cited by 14 publications

References 46 publications

Structures, Properties, and Device Applications for [1]Benzothieno[3,2‐b]Benzothiophene Derivatives

Structures, Properties, and Device Applications for [1]Benzothieno[3,2‐b]Benzothiophene Derivatives

Homogeneous and Heterogeneous Gold Catalysis for Materials Science

Deposition-Dependent Morphology and Infrared Vibrational Spectra of Brominated Tetraazaperopyrene Layers

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