An Efficient Route to Stable Room‐Temperature Liquid‐Crystalline Triphenylenes

Böck, Harald; Rajaoarivelo, Mbolotiana; Clavaguera, Simon; Grelet, Éric

doi:10.1002/ejoc.200600116

Cited by 38 publications

(20 citation statements)

References 18 publications

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“…Photooxidation of the crude mixture of light sensitive diphenyl isomers was performed without prior attempt to separate them, because both lead to the targeted dibenzocoronene‐tetraester 10 Et . Triphenylene 12 was obtained on a large scale according to established procedures by ZrCl 4 ‐catalyzed cyclodehydration of cyclohexanone followed by Pd‐catalyzed dehydrogenation, in analogy to our previous synthesis of 2,6,10‐trimethyltriphenylene …”

Section: Methodsmentioning

confidence: 99%

Isomeric Column‐Forming Esters and Imides with Varying Curvatures of the Aromatic Plane

Ferreira

Moreira

Cristiano

et al. 2018

Chemistry A European J

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Dibenzo[a,j]coronene-tetracarboxylic alkyl esters and imides with either a centrosymmetric bis-peri substitution pattern or a polar bis-ortho substitution pattern form hexagonal columnar mesophases, which in the case of the imides persist at room temperature. The bis-peri isomers are obtained via a two-fold oxidative photocyclization; the bis-ortho isomers are accessed via a glyoxylic Perkin reaction of triphenylene and naphthalene building blocks. Steric congestion between the substituents and the adjacent benzo protrusion in the bis-ortho esters and imides leads to bending of the aromatic plane, which thus avoids twisting. These isomers surprisingly show a more pronounced liquid crystalline behaviour than their non-bent bis-peri homologs, accommodating non-planarity with columnar order by slipped stacking. Whereas both types of ester and the bis-peri imide show an optical behaviour typical for perylene chromophores, the strongly bent bis-ortho imide distinguishes itself notably from them by its absorption spectrum. The electron acceptor strength of the isomeric diimides is found to differ, the hexagonal (peri) diimide having a 0.20 eV lower LUMO energy than the pentagonal (ortho) isomer.

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Section: Methodsmentioning

confidence: 99%

Isomeric Column‐Forming Esters and Imides with Varying Curvatures of the Aromatic Plane

Ferreira

Moreira

Cristiano

et al. 2018

Chemistry A European J

Self Cite

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“…5), many of which have been tested in devices. Experimental studies have studied the effect of aromatic core size 104 and side-chains 105 on phase behaviour 102,103 and charge mobility. 106,107 Despite the wealth of experimental studies a detailed microscopic understanding of the charge mobility in discotic materials is still lacking.…”

Section: Semiconducting Liquid Crystalsmentioning

confidence: 99%

Modelling charge transport in organic semiconductors: from quantum dynamics to soft matter

Cheung

Troisi

2008

Phys. Chem. Chem. Phys.

144

175

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The charge carrier dynamics in organic semiconductors has been traditionally discussed with the models used in inorganic crystalline and amorphous solids but this analogy has severe limitations because of the more complicated role of nuclear motions in organic materials. In this perspective, we discuss how a new approach to the modelling of charge transport is emerging from the alliance between the conventional quantum chemical methods and the methods more traditionally used in soft-matter modelling. After describing the conventional limit cases of charge transport we discuss the problems arising from the comparison of the theory with the experimental and computational results. Several recent applications of numerical methods based on the propagation of the wavefunction or kinetic Monte Carlo methods on soft semiconducting materials are reviewed.

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“…Polycyclic aromatic hydrocarbons (PAH) are one of the major materials for preparing crystalline nanostructures that possess semiconducting and photoluminescence properties [12][13][14]. The main driving force for self-assembling 1D PAH nanostructures is the p2p interactions of PAH or PAH derivatives [15][16][17].…”

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confidence: 99%

Optoelectronic property and sensing applications of crystalline nano/microwires of decacyclene

Wang

et al. 2011

Micro Nano Lett.

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The characterisation and potential sensing applications of nano-and microwires of decacyclene are reported in this study. Attenuated total reflection infrared and differential thermal analyses reveal that the nano/microstructures are composed of aggregated decacyclene molecules that are held by p-p interactions. Transmission electron microscopy images and the electron diffraction patterns show that, in the nanowires, the decacyclene molecules are oriented with their long axis perpendicular to the wires and the p-p stacking direction parallel to the wire. Cross-optical polarised microscopy results shows a birefringent crystal structure of the decacyclene crystalline wires. Fluorescent imaging shows that the crystalline wires might be used as a waveguide material. Both the conductivity and fluorescence of the nanobelts change selectively in the presence of vapour of nitrobenzene, a representative nitroaromatic, suggesting that the nanowires of decacyclene may be used for selective detection of explosives.

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An Efficient Route to Stable Room‐Temperature Liquid‐Crystalline Triphenylenes

Cited by 38 publications

References 18 publications

Isomeric Column‐Forming Esters and Imides with Varying Curvatures of the Aromatic Plane

Isomeric Column‐Forming Esters and Imides with Varying Curvatures of the Aromatic Plane

Modelling charge transport in organic semiconductors: from quantum dynamics to soft matter

Optoelectronic property and sensing applications of crystalline nano/microwires of decacyclene

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