Polymorphism in<i>N</i>,<i>N</i>′-dialkyl-naphthalene diimides

Milita, Silvia; Liscio, Fabiola; Cowen, Lewis; Cavallini, Massimiliano; Drain, Ben; Degousée, Thibault; Luong, Sally; Fenwick, Oliver; Guagliardi, Antonietta; Schroeder, Bob C.; Masciocchi, Norberto

doi:10.1039/c9tc06967d

Cited by 21 publications

(51 citation statements)

References 54 publications

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“…These features suggest that the C 10 -DNTT on crosslinked polymeric films exhibit a higher crystalline order and texturing than that of the pristine polymeric layers; in particular, the grain is oriented along one specific direction relative to the normal of the substrate surface. [27] Figure 3. OSC morphology characteristics: a) surface topographies and b) 2D-GIXD images of C 10 -DNTT deposited on the polymeric dielectrics.…”

Section: Osc Crystal Formationmentioning

confidence: 99%

Newly Synthesized Nonvacuum Processed High‐k Polymeric Dielectrics with Carboxyl Functionality for Highly Stable Operating Printed Transistor Applications

Kwon

Shim

et al. 2020

Adv Funct Materials

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Solution‐processed polar hydroxyl containing polymers such as poly(4‐vinylphenol) are widely utilized in organic filed‐effect transistors (OFETs) due to their high dielectric constant (k) and excellent insulating properties owing to the crosslinking through their hydroxyl groups. However, hydroxyl functionalities can function as trapsites, and their crosslinking reactions decrease the k value of materials. Hence, in this study, new solution‐processable copolymers containing both carboxyl and hydrophobic functionalities are synthesized. A fluorophenyl azide (FPA) based UV‐assisted crosslinker is also employed to promote the movement of polar carboxyl groups toward the bulk region and the hydrophobic functionalities to the surface region, thereby maintaining the high‐k characteristics and hydrophobic surface in thin film. Thus, the addition of an FPA crosslinker eliminates the trapsites on the surface, allowing a stable operation and efficient charge transport. Additionally, the solution‐processability enables the production of uniform and thin films to yield OFETs with stable and low‐voltage driving characteristics. The printed layers are also applied as gate dielectrics for floating gate memory devices and in integrated one‐transistor‐one‐transistor based memory cells, displaying their excellent memory performance. The synthesis and fabrication strategies employed in this study can become useful guidelines for the production of high‐k dielectrics for stable OFETs and other applications.

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Section: Osc Crystal Formationmentioning

confidence: 99%

Newly Synthesized Nonvacuum Processed High‐k Polymeric Dielectrics with Carboxyl Functionality for Highly Stable Operating Printed Transistor Applications

Kwon

Shim

et al. 2020

Adv Funct Materials

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“…In the bulk, the β phase was previously observed to form at high temperature, but was kinetically stabilized upon cooling to room temperature [ 26 ]. The existence of a minor amount of metastable phase at room temperature in spin-coated thin films has been previously reported [ 46 , 47 ]. It is possible that the formation of a minor amount of the β phase can be explained by the much faster crystallization rate during the spin-coating process, as compared to the conventional chemical bench work-up.…”

Section: Resultsmentioning

confidence: 94%

Highly Stable Thin Films Based on Novel Hybrid 1D (PRSH)PbX3 Pseudo-Perovskites

et al. 2021

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In this study, the structure and morphology, as well as time, ultraviolet radiation, and humidity stability of thin films based on newly developed 1D (PRSH)PbX3 (X = Br, I) pseudo-perovskite materials, containing 1D chains of face-sharing haloplumbate octahedra, are investigated. All films are strongly crystalline already at room temperature, and annealing does not promote further crystallization or film reorganization. The film microstructure is found to be strongly influenced by the anion type and, to a lesser extent, by the DMF/DMSO solvent volume ratio used during film deposition by spin-coating. Comparison of specular X-ray diffraction and complementary grazing incidence X-ray diffraction analysis indicates that the use of DMF/DMSO mixed solvents promotes the strengthening of a dominant 100 or 210 texturing, as compared the case of pure DMF, and that the haloplumbate chains always lie in a plane parallel to the substrate. Under specific DMF/DMSO solvent volume ratios, the prepared films are found to be highly stable in time (up to seven months under fluxing N2 and in the dark) and to highly moist conditions (up to 25 days at 78% relative humidity). Furthermore, for representative (PRSH)PbX3 films, resistance against ultraviolet exposure (λ = 380 nm) is investigated, showing complete stability after irradiation for up to 15 h at a power density of 600 mW/cm2. These results make such thin films interesting for highly stable perovskite-based (opto)electronic devices.

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“…Arrangement of molecules in the columns. The mutual shift of the planar molecules within molecular columns can be described phenomenologically using different pairs of geometric parameters -'pitch and roll' inclinations (Curtis et al, 2004) or direction cosines of the shift vector (Milita et al, 2020).…”

Section: Comparison With Crystal Structures Of Other Cupc Derivativesmentioning

confidence: 99%

Crystal structure of copper perchlorophthalocyanine analysed by 3D electron diffraction

Gorelik

Habermehl

Shubin

et al. 2021

Acta Crystallogr B Struct Sci Cryst Eng Mater

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Copper perchlorophthalocyanine (CuPcCl16, CuC32N8Cl16, Pigment Green 7) is one of the commercially most important green pigments. The compound is a nanocrystalline fully insoluble powder. Its crystal structure was first addressed by electron diffraction in 1972 [Uyeda et al. (1972). J. Appl. Phys. 43, 5181–5189]. Despite the commercial importance of the compound, the crystal structure remained undetermined until now. Using a special vacuum sublimation technique, micron-sized crystals could be obtained. Three-dimensional electron diffraction (3D ED) data were collected in two ways: (i) in static geometry using a combined stage-tilt/beam-tilt collection scheme and (ii) in continuous rotation mode. Both types of data allowed the crystal structure to be solved by direct methods. The structure was refined kinematically with anisotropic displacement parameters for all atoms. Due to the pronounced crystal mosaicity, a dynamic refinement was not feasible. The unit-cell parameters were verified by Rietveld refinement from powder X-ray diffraction data. The crystal structure was validated by many-body dispersion density functional theory (DFT) calculations. CuPcCl16 crystallizes in the space group C2/m (Z = 2), with the molecules arranged in layers. The structure agrees with that proposed in 1972.

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Polymorphism inN,N′-dialkyl-naphthalene diimides

Abstract: N-Alkyl naphthalene diimides show a highly versatile thermally-induced polymorphic behavior, including liquid crystalline mesophases, fully characterized in powders and thin films by combining thermal, diffraction and imaging techniques.

Cited by 21 publications

References 54 publications

Newly Synthesized Nonvacuum Processed High‐k Polymeric Dielectrics with Carboxyl Functionality for Highly Stable Operating Printed Transistor Applications

Newly Synthesized Nonvacuum Processed High‐k Polymeric Dielectrics with Carboxyl Functionality for Highly Stable Operating Printed Transistor Applications

Highly Stable Thin Films Based on Novel Hybrid 1D (PRSH)PbX3 Pseudo-Perovskites

Crystal structure of copper perchlorophthalocyanine analysed by 3D electron diffraction

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