Real-Time Structural and Optical Study of Growth and Packing Behavior of Perylene Diimide Derivative Thin Films: Influence of Side-Chain Modification

Belova, Valentina; Wagner, Benjamin; Reisz, Berthold; Zeiser, Clemens; Duva, Giuliano; Rozbořil, Jakub; Novák, Jiřı́; Gerlach, Alexander; Hinderhofer, Alexander; Schreiber, Frank

doi:10.1021/acs.jpcc.8b00787

Cited by 21 publications

(46 citation statements)

References 113 publications

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“…The ultimate reason for this effect might be found in the bulkiness and the larger van der Waals radius of fluorine atoms that reduce the flexibility of the related chains. It is also interesting to observe that the hydrophobic degree of the SiO 2 surface plays a crucial role in the appearance of the polymorphic phases here discussed [25,53]. Figure 5b, a zoomed-in view of a crystalline island and estimation of the molecular step height for the film grown at T SUB = 140 • C is given.…”

Section: Pdif-cn 2 Devices Fabricated Using the Ombd Techniquementioning

confidence: 78%

“…The presence of different polymorphic phases was also invoked by H. Klauk and co-authors discussing the morphological properties of similar PDIF-CN 2 films evaporated at T SUB = 140 • C on octadecyltrichlorosilane-treated SiO 2 [25]. It is natural that the more complex behavior of PDIF-CN 2 in comparison with PDI8-CN 2 has to be fully ascribed to the presence of the fluorinated chains, which in comparison with the simple alkyl chains, tend to provide a higher overall steric hindrance and to hamper the crystallization phenomenon [53]. The ultimate reason for this effect might be found in the bulkiness and the larger van der Waals radius of fluorine atoms that reduce the flexibility of the related chains.…”

Section: Pdif-cn 2 Devices Fabricated Using the Ombd Techniquementioning

confidence: 99%

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Perylene-Diimide Molecules with Cyano Functionalization for Electron-Transporting Transistors

et al. 2019

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Core-cyanated perylene diimide (PDI_CY) derivatives are molecular compounds exhibiting an uncommon combination of appealing properties, including remarkable oxidative stability, high electron affinities, and excellent self-assembling properties. Such features made these compounds the subject of study for several research groups aimed at developing electron-transporting (n-type) devices with superior charge transport performances. After about fifteen years since the first report, field-effect transistors based on PDI_CY thin films are still intensely investigated by the scientific community for the attainment of n-type devices that are able to balance the performances of the best p-type ones. In this review, we summarize the main results achieved by our group in the fabrication and characterization of transistors based on PDI8-CN2 and PDIF-CN2 molecules, undoubtedly the most renowned compounds of the PDI_CY family. Our attention was mainly focused on the electrical properties, both at the micro and nanoscale, of PDI8-CN2 and PDIF-CN2 films deposited using different evaporation techniques. Specific topics, such as the contact resistance phenomenon, the bias stress effect, and the operation in liquid environment, have been also analyzed.

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Section: Pdif-cn 2 Devices Fabricated Using the Ombd Techniquementioning

confidence: 78%

Section: Pdif-cn 2 Devices Fabricated Using the Ombd Techniquementioning

confidence: 99%

Perylene-Diimide Molecules with Cyano Functionalization for Electron-Transporting Transistors

et al. 2019

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“…MD was performed by integrating the equation of motions with a finite time-step of 1 fs. Models of crystalline bilayers of PDIF-CN 2 and PDI8-CN 2 molecules, respectively, were initially built using the cell parameters present in literature, and subsequently equilibrating the systems for 1 ns at 300 K. [21,25] Both the PDIF-CN 2 and PDI8-CN 2 2D models were put in contact with water molecules and equilibrated at 300 K for 10 ns, computing structural parameters as averages of the last 5 ns. All the MD calculations were performed with the Gromacs program package.…”

Section: Methodsmentioning

confidence: 99%

3D versus 2D Electrolyte–Semiconductor Interfaces in Rylenediimide‐Based Electron‐Transporting Water‐Gated Organic Field‐Effect Transistors

Prescimone

Benvenuti

Natali

et al. 2020

Adv Elect Materials

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aqueous electrolyte solution acting as the gate dielectric in contact with the organic semiconductor (OS). [1,2] This kind of architecture enables the WGOFET to transduce bioelectrical signals and to detect molecular analytes, ions, and biomarkers. [1,3,4] In WGOFETs the charge accumulation in the OS is caused by the electrolyte ions migrating close to the OS interface and to the gate interface when a gate potential is applied. [5,6] Thus, charge accumulation in the OS film and charge transport occur close to OS/electrolyte interface. In this scenario, the structural organization and the morphological features of the OS/ electrolyte interface play a crucial role in the device performance, as expected in any class of field-effect transistors based on thin films. The growth mechanism of the active layer as the thin-film layer thickness is increased typically controls the film morphology and molecular organization of the interface that is finally exposed to water, as it is in the case of standard OFET devices with a top-gate configuration. [6-8] Among the plethora of organic semiconductors with different molecular structures and tailored electrical properties, thin films comprised by linear molecular systems, like pentacene and α-sexithiophene, are subjected to a transition from a layer-by-layer to island growth upon completion of a few molecular monolayers (5-6 nm). [9-12] This growth mechanism Water-gated organic field-effect transistors (WGOFETs) are relevant devices for use in the fields of biosensors and biosystems. However, real applications require very stringent performance in terms of electrochemical stability and charge mobility to the organic semiconductor in contact with an aqueous environment. Here, a comparative study of two small-molecule electrontransporting perylenediimide semiconductors, which differ only in the N-substituents named PDIF-CN 2 and PDI8-CN 2 is reported. The two materials present similar solid-state arrangements but, while the PDI8-CN 2 shows a more 3D growth modality and electron mobility independent of the semiconductor layer thickness (≈10 −4 cm 2 V −1 s −1), the PDIF-CN 2 has an almost-2D growth modality and the mobility increases with the semiconductor film thickness, reaching a maximum value of ≈5 × 10 −3 cm 2 V −1 s −1 at 30 nm. Above this thickness, the PDIF-CN 2 switches to a more 3D growth modality, and the mobility drops by one order of magnitude. XRR analysis indicates that a PDIF-CN 2 film can be modeled as a dense layered structure in which each layer is decoupled from the others due to the presence of fluorocarbonchains. The availability of additional pathways for charge transport from buried layers and the 2D versus 3D growth can explain the mobility dependence on the film thickness.

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“…Among different types of organic donors (p-type polymers) and organic acceptors (n-type polymers), perylene diimide (PDI) derivatives represent a well-known family of electron-accepting small molecule OSC. Hydrogenated PDIR-CN2 and fluorinated PDIF-CN2 version of PDI molecules deposited with organic molecular beam deposition method on top of native silicon oxide demonstrated an increase of lateral and transversal crystallinity upon heating the film from room temperature to 110-160 • C, whereas PDIF-CN2 is poorly ordered at room temperature right after deposition [219] as shown in Figure 23. The charge transfer between electron donor and electron acceptor molecules at interfaces or in mixed molecular systems is one of the fundamental processes in devices based on OSC.…”

Section: Polymer Photovoltaicsmentioning

confidence: 99%

Synchrotron Scattering Methods for Nanomaterials and Soft Matter Research

Narayanan

Konovalov

2020

Materials

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This article aims to provide an overview of broad range of applications of synchrotron scattering methods in the investigation of nanoscale materials. These scattering techniques allow the elucidation of the structure and dynamics of nanomaterials from sub-nm to micron size scales and down to sub-millisecond time ranges both in bulk and at interfaces. A major advantage of scattering methods is that they provide the ensemble averaged information under in situ and operando conditions. As a result, they are complementary to various imaging techniques which reveal more local information. Scattering methods are particularly suitable for probing buried structures that are difficult to image. Although, many qualitative features can be directly extracted from scattering data, derivation of detailed structural and dynamical information requires quantitative modeling. The fourth-generation synchrotron sources open new possibilities for investigating these complex systems by exploiting the enhanced brightness and coherence properties of X-rays.

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Real-Time Structural and Optical Study of Growth and Packing Behavior of Perylene Diimide Derivative Thin Films: Influence of Side-Chain Modification

Cited by 21 publications

References 113 publications

Perylene-Diimide Molecules with Cyano Functionalization for Electron-Transporting Transistors

Perylene-Diimide Molecules with Cyano Functionalization for Electron-Transporting Transistors

3D versus 2D Electrolyte–Semiconductor Interfaces in Rylenediimide‐Based Electron‐Transporting Water‐Gated Organic Field‐Effect Transistors

Synchrotron Scattering Methods for Nanomaterials and Soft Matter Research

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