2,7‐Carbazolenevinylene‐Based Oligomer Thin‐Film Transistors: High Mobility Through Structural Ordering

Drolet, Nicolas; Morin, Jean‐François; Leclerc, Nicolas; Wakim, Salem; Tao, Ye; Leclerc, Mario

doi:10.1002/adfm.200500168

Cited by 142 publications

(91 citation statements)

References 60 publications

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“…These phenomena may explain by H-aggregates or J-aggregates, which are usually related to excitonic coupling between adjacent molecules in a closely packed structure. 41 In the PL spectra, the thin films of all compounds showed a large degree of red-shift relative to their solution spectra. The results may also originate from the aggregation or excimer formation due to π→π * stacking or intermolecular interaction caused by their planar structures (Figure 1).…”

Section: Resultsmentioning

confidence: 99%

Chain Length Effect of Dialkoxynaphthalene End-Capped Divinylbenzene for OTFT

Kim¹,

Yun²,

Yi³

et al. 2012

Bulletin of the Korean Chemical Society

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The new organic semiconductors which are composed of divinylbenzene core unit and alkoxynaphthalene on both sides, 1,4-bis-2-(6-octyloxy)naphthalen-2-ylvinylbenzene (BONVB), 1,4-bis-2-(6-decyloxy)naphthalen-2-ylvinylbenzene (BDNVB) and 1,4-bis-2-(6-dodecyloxy)naphthalen-2-ylvinylbenzene (BDDNVB) were synthesized by Wittig reaction. The structures of obtained BONVB, BDNVB and BDDNVB were confirmed by FT-IR and mass spectroscopy. UV-absorption of thin film showed H-aggregates and J-aggregates due to closely packed structure between adjacent molecules. The characterization of vacuum-evaporated films by Xray diffraction (XRD) and atomic force microscopy (AFM) showed that the chain length of alkoxy group affects the crystallinity and morphology. BONVB with octyloxy group showed the mobility of 0.011 cm 2 /V·s, on/off ratio of 1.31 × 10 5, and a subthreshold slope of 0.93 V.

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Section: Resultsmentioning

confidence: 99%

Chain Length Effect of Dialkoxynaphthalene End-Capped Divinylbenzene for OTFT

Kim¹,

Yun²,

Yi³

et al. 2012

Bulletin of the Korean Chemical Society

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“…Since carbazole has prominent optical and electronic properties and is chemically stable, carbazole derivatives have been studied for use in a variety of applications, including organic light-emitting diodes (OLEDs), [136] nonlinear optics (NLOs), [137] and organic field-effect transistors (OFETs).…”

Section: Carbazole-containing Macrocycles and Related Compoundsmentioning

confidence: 99%

Conjugated Macrocycles: Concepts and Applications

2011

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One of the most important objectives in materials, chemical, and physical sciences is the creation of large conjugated macrocycles with well-defined shapes, since such molecules are not only theoretically and experimentally interesting but also have potential applications in nanotechnology. Fully unsaturated macrocycles are regarded as models for infinitely conjugated π systems with inner cavities, and exhibit unusual optical and magnetic behavior. Macrocycles have interior and exterior sites, and site-specific substitution at both or either site can afford attractive structures, such as 1D, 2D, and 3D supramolecular nanostructures. These nanostructures could be controlled through the use of π-extended large macrocycles by a bottom-up strategy. Numerous shape-persistent π-conjugated macrocycles have been synthesized, but only a few are on the nanoscale. This Review focuses on nanosized π-conjugated macrocycles (>1 nm diameter) and giant macrocycles (>2 nm diameter), and summarizes their syntheses and properties.

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“…Namely, materials based on them are very promising because of their great stability, good solubility, excellent photoconductive properties, relatively intense luminescence, and good performance in OFETs, OLEDs, and thermoelectric materials [42][43][44][45][46][47][48][49][50][51][52]. Moreover, these compounds, and particularly halogenated carbazoles, are important synthetic intermediates and pharmacological targets [53].…”

Section: Introductionmentioning

confidence: 99%

Two isostructural halogen derivatives of 9-ethylcarbazole: crystal structure, Hirshfeld surface analysis, and structural comparison with other simple analogs

et al. 2015

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This article describes a detailed study of the molecular packing and intermolecular interactions in crystals of two derivatives of 9-ethylcarbazole, i.e., 3-chloro-and 3-bromo-9-ethylcarbazole (1 and 2, respectively). A significance of this study lies both in the comparison drawn between the crystal structures of these compounds and those of several of their simple analogs [i.e., 3,6-dibromo-9-ethylcarbazole (3), 3,6-dibromo-9-methylcarbazole (4), 3,6-dibromocarbazole (5), 3-bromocarbazole (6), 3,6-diiodocarbazole (7), 9-ethylcarbazole (8), 9-methylcarbazole (9) and carbazole (10)], and in the preliminary assessment of their suitability as active materials for organic electronics. This comparison shows a close similarity in the packing of molecules of three of them (i.e., 3, 4, 6) that form the p-stacks along the shortest crystallographic axes, with a substantial spatial overlap between adjacent molecules in the stacks, depending mainly on the length of substituent at position 9 of carbazole skeleton and on the ratio of (%CÁÁÁH)/(%CÁÁÁC) interactions. Similar to them, in the crystal structures of 1 and 2 there is slipped face-to-face pÁÁÁp interaction, but in contrast this interaction connects two molecules of these compounds into the dimers that are further connected by C-HÁÁÁp interaction. The molecular packing in crystals of these compounds is intermediate between the arrangement of molecules of 3, 4, and 6, where the slipped p-stacking is predominant, and the typical herringbone packing in compounds 5 and 7-10. Thus, it can be supposed that out of ten compounds analyzed here, only 3, 4, and 6 will turn to be the most promising materials for device applications (particularly for field-effect transistors).

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2,7‐Carbazolenevinylene‐Based Oligomer Thin‐Film Transistors: High Mobility Through Structural Ordering

Cited by 142 publications

References 60 publications

Chain Length Effect of Dialkoxynaphthalene End-Capped Divinylbenzene for OTFT

Chain Length Effect of Dialkoxynaphthalene End-Capped Divinylbenzene for OTFT

Conjugated Macrocycles: Concepts and Applications

Two isostructural halogen derivatives of 9-ethylcarbazole: crystal structure, Hirshfeld surface analysis, and structural comparison with other simple analogs

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