Crystal and Electronic Structure of a Fluorescent Columnar Liquid Crystalline Electron Transport Material

Séguy, Isabelle; Jolinat, Pascale; Destruel, P.; Allouchi, Hassan; Courseille, C.; Cotrait, M.; Böck, Harald

doi:10.1002/1439-7641(20010716)2:7<448::aid-cphc448>3.0.co;2-#

Cited by 76 publications

(78 citation statements)

References 32 publications

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“…These redox events with potentials of +1.03, −0.99, −1.18, −1.59, and −1.68 V exhibited roughly the same integrated current, indicating single‐electron‐transfer processes. Considering the energy level of ferrocene/ferrocenium (Fc/Fc + ) with respect to the vacuum level (−4.8 eV),25 the HOMO and LUMO energy levels of 1 can be estimated using its experimentally determined redox potentials. The obtained values of −3.81 eV for the LUMO and −5.83 eV for the HOMO level (Figure 2) are in good agreement with our DFT calculations.…”

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confidence: 99%

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An Electron‐Poor C₆₄ Nanographene by Palladium‐Catalyzed Cascade C−C Bond Formation: One‐Pot Synthesis and Single‐Crystal Structure Analysis

et al. 2016

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Herein, we report the one‐pot synthesis of an electron‐poor nanographene containing dicarboximide groups at the corners. We efficiently combined palladium‐catalyzed Suzuki–Miyaura cross‐coupling and dehydrohalogenation to synthesize an extended two‐dimensional π‐scaffold of defined size in a single chemical operation starting from N‐(2,6‐diisopropylphenyl)‐4,5‐dibromo‐1,8‐naphthalimide and a tetrasubstituted pyrene boronic acid ester as readily accessible starting materials. The reaction of these precursors under the conditions commonly used for Suzuki–Miyaura cross‐coupling afforded a C64 nanographene through the formation of ten C−C bonds in a one‐pot process. Single‐crystal X‐ray analysis unequivocally confirmed the structure of this unique extended aromatic molecule with a planar geometry. The optical and electrochemical properties of this largest ever synthesized planar electron‐poor nanographene skeleton were also analyzed.

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“…[a] Calculated according to literature‐known procedures using the experimentally determined redox potentials ( E LUMO =−[ E (M/M − )+4.8 eV] and E HOMO =−[ E (M/M + )+4.8 eV]) and the energy level of ferrocene/ferrocenium (Fc/Fc + ) with respect to the vacuum level (−4.8 eV) 25. [b] DFT calculated values (B3‐LYP, def2‐SVP).…”

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An Electron‐Poor C₆₄ Nanographene by Palladium‐Catalyzed Cascade C−C Bond Formation: One‐Pot Synthesis and Single‐Crystal Structure Analysis

et al. 2016

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“…Table 1 summarizes the potentials quoted relative to the ferrocenium/ferrocene couple. [19] The converted energy levels are also summarized in Table 1 for comparison. Assuming that the Koopman's theorem holds (EA red ≈ -LUMO red ), [18] the LUMO levels can be estimated from the first half-wave reduction potentials by taking the ferrocene energy level to be -4.8 eV below the vacuum level.…”

Section: Synthesis Crystal Structure and Electrochemical Propertiesmentioning

confidence: 99%

Synthesis, Photophysical Properties, and Field‐Effect Characteristics of (Ethynylphenyl)benzimidazole‐Decorated Anthracene and Perylene Bisimide Derivatives

Lee

Chen

et al. 2012

Eur J Org Chem

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A series of anthracene and perylene bisimide derivatives with electron‐withdrawing benzimidazole substituents has been designed and prepared. Detailed studies on the electrochemical and photophysical properties as well as the field‐effect mobilities of these new compounds were explored. The incorporation of electron‐withdrawing benzimidazole groups lowered the LUMO levels in both anthracene and perylene bisimide derivatives compared to those of the parent compounds. Strong emission was observed for all anthracene derivatives, but only weak emission was observed for perylene bisimide derivatives. The anthracene derivatives showed typical p‐type semiconducting character, even when the derivatives were substituted with electron‐withdrawing benzimidazole groups at the 9‐ and 10‐positions, which apparently does not lower the LUMO levels to transform them into electron‐transporting molecules. Perylene bisimide derivatives displayed typical n‐channel semiconducting properties with low threshold voltages and electron mobilities of ca. 5.2 × 10–5 cm2 V–1 s–1.

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“…Most of these compounds are crystalline at room temperature and show a hexagonal columnar phase at higher temperatures (table 1). X-ray investigations [25] have shown that the columnar structure of some of these compounds is preserved when they are cooled from the columnar into the solid phase. The new perylene diimides (4) [which were synthesized at the University of Hull] show a mesogenic molecular structure but no enantiotropic mesophase.…”

Section: Investigated Compoundsmentioning

confidence: 99%

Electroluminescence and photovoltaic effects using columnar mesogenic compounds

et al. 2003

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Columnar liquid crystals are useful for the construction of organic light emitting diodes (OLED) due to their high charge carrier mobility and their ability of developing defect-free superstructures. We investigated the electroluminescent properties of various mesogenic derivatives of triphenylene, pyrene, perylene, benzoperylene and hexa-perihexabenzocoronene (HBC) which combine good charge carrying properties and luminescence. The wavelengths of maximum electroluminescence range from about 400 nm to 720 nm, depending on the core and the substitution of the molecules. Nearly white emission can be obtained in samples containing two or more emitting layers. The perylene core is so efficient that even a single organic layer between an ITO anode and an aluminum cathode can give luminance values up to 100 cd/m 2 . In addition to the electroluminescence, we present results on the photovoltaics in hetero junction structures of the compounds. Samples with two organic layers made of a HBC-and a perylene derivative show an open circuit voltage V oc of about 0.8 V, a short circuit current I sc of a few µA/cm 2 , and a filling factor FF of approximately 31 %.

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Crystal and Electronic Structure of a Fluorescent Columnar Liquid Crystalline Electron Transport Material

Cited by 76 publications

References 32 publications

An Electron‐Poor C₆₄ Nanographene by Palladium‐Catalyzed Cascade C−C Bond Formation: One‐Pot Synthesis and Single‐Crystal Structure Analysis

An Electron‐Poor C₆₄ Nanographene by Palladium‐Catalyzed Cascade C−C Bond Formation: One‐Pot Synthesis and Single‐Crystal Structure Analysis

Synthesis, Photophysical Properties, and Field‐Effect Characteristics of (Ethynylphenyl)benzimidazole‐Decorated Anthracene and Perylene Bisimide Derivatives

Electroluminescence and photovoltaic effects using columnar mesogenic compounds

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Crystal and Electronic Structure of a Fluorescent Columnar Liquid Crystalline Electron Transport Material

Cited by 76 publications

References 32 publications

An Electron‐Poor C64 Nanographene by Palladium‐Catalyzed Cascade C−C Bond Formation: One‐Pot Synthesis and Single‐Crystal Structure Analysis

An Electron‐Poor C64 Nanographene by Palladium‐Catalyzed Cascade C−C Bond Formation: One‐Pot Synthesis and Single‐Crystal Structure Analysis

Synthesis, Photophysical Properties, and Field‐Effect Characteristics of (Ethynylphenyl)benzimidazole‐Decorated Anthracene and Perylene Bisimide Derivatives

Electroluminescence and photovoltaic effects using columnar mesogenic compounds

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An Electron‐Poor C₆₄ Nanographene by Palladium‐Catalyzed Cascade C−C Bond Formation: One‐Pot Synthesis and Single‐Crystal Structure Analysis

An Electron‐Poor C₆₄ Nanographene by Palladium‐Catalyzed Cascade C−C Bond Formation: One‐Pot Synthesis and Single‐Crystal Structure Analysis