Discotic Liquid Crystals

Wöhrle, Tobias; Wurzbach, Iris; Kirres, Jochen; Kostidou, Antonia; Kapernaum, Nadia; Litterscheidt, Juri; Haenle, Johannes Christian; Staffeld, Peter; Baro, Angelika; Gießelmann, Frank; Laschat, Sabine

doi:10.1021/acs.chemrev.5b00190

Cited by 666 publications

(435 citation statements)

References 684 publications

(1,110 reference statements)

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“…[2] Columnar self-assemblies based on benzene-1,3,5-tricarboxamide (BTA) motif result from π-π stacking interactions and formation of maximal number of hydrogen bonds between the individual units. [3][4][5][6] These discotic systems [7] are characterized by a helical arrangement of units and have attracted attention as organic electronic elements due to their liquid crystal features. [8] Detailed studies of their aggregation process have highlighted the cooperative nature of these self-assemblies.…”

Section: Introductionmentioning

confidence: 99%

Columnar self-assembly of N,N′,N′′-trihexylbenzene-1,3,5-tricarboxamides investigated by means of NMR spectroscopy and computational methods in solution and the solid state

Banach

Invernizzi

Baudin

et al. 2017

Phys. Chem. Chem. Phys.

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Section: Introductionmentioning

confidence: 99%

Columnar self-assembly of N,N′,N′′-trihexylbenzene-1,3,5-tricarboxamides investigated by means of NMR spectroscopy and computational methods in solution and the solid state

Banach

Invernizzi

Baudin

et al. 2017

Phys. Chem. Chem. Phys.

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“…The conventional DLC molecules comprise a planar rigid core and several aliphatic chains, normally through ether, thioether, or ester bonds peripherally attached to the cores [23][24][25]. The majority of DLCs are thermotropic liquid crystals and have a strong tendency for columnar mesophase formation.…”

Section: Introductionmentioning

confidence: 99%

Mesogenic complementary absorbing dyads based on porphyrin and perylene units

Kong

Gong

Dai

et al. 2018

J. Porphyrins Phthalocyanines

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Five novel dyads, consisting of a tetraphenylporphyrine unit connected to a perylene monoimide diester unit via a flexible bridge -CONH-(CH 2 ) n -(n = 4, 6, 8, 10 and 12), have been synthesized. Their structures were characterized by 13 C and 1 H nuclear magnetic resonance spectroscopy, infrared spectroscopy, mass spectrometry and elemental analysis. The UV-vis absorption spectra revealed these dyads have broad optical absorption in the ultraviolet and visible regions due to the complementary absorption of the two units. The differential scanning calorimetry traces and polarized optical microscopy textures showed all these dyads have columnar liquid crystal phases. Cyclic voltammetry revealed the highest occupied molecular orbitals of the dyads located on the porphyrin units, and the lowest unoccupied molecular orbitals located on the perylene units. In addition, these results were in agreement with that of the theoretical modeling. When excited at 423 or 473 nm, the photoluminescent emission spectra showed that the degree of fluorescence quenching of porphyrin units increased as the spacers became shorter. This quenching was ascribed to intramolecular photoinduced electron transfer, which also induced the dyad molecules to form the charge-separated states. The charge-separated molecules were further confirmed by the photocurrent response curves. These behaviors of broad absorption of the ultraviolet-visible light, yielding the charge-separated states of the molecules when excited and the formation of columnar liquid crystal phase made these dyads candidates for single-component photovoltaic active materials.

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“…[1][2][3] The strong intermolecular interactions between the large planar aromatic surfaces incur favorable tendency for such molecules to stack into one-dimensional (1D) columns, which can serve as the preferred charge carrier transporting pathway through inter-stack hopping. In the solid state, these 1D columns can further organize into two dimensional suprastructures.…”

Section: Introductionmentioning

confidence: 99%

“…There are abundant examples of hole-transporting disk-shaped molecules, however these with good electron-transporting properties remain underdeveloped and thus require much more research endeavor. 3 From a molecular design point of view, the nature of the charge carriers could be empirically engineered by adjusting the electron density of the aromatic unit. Introduction of electron deficient nitrogen atoms [5][6][7][8] onto the aromatic core has been an effective method in endowing n-type characteristics.…”

Section: Introductionmentioning

confidence: 99%

Understanding Electron Transport in Disk-Shaped Triphenylene-Tris(naphthaleneimidazole)s through Structural Modification and Theoretical Investigation

Zhang

Hanifi

Fernández‐Liencres

et al. 2017

ACS Appl. Mater. Interfaces

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ABSTRACT. Disk-shaped molecules with large aromatic π-surface are a class of organic semiconductors of which the charge carrier transport properties could be greatly facilitated by preferred intermolecular stacking of the π-surfaces. The optical and electronic properties are not only determined by the core aromatic structure of these disk-shaped molecules, but also strongly dependent on the sidechains, which directly impact the molecular self-assembly behavior in condensed phases. Triphenylene-tris(naphthaleneimidazole) (TP-TNI) is a recently reported ntype semiconductor featuring a large π-core and branched sidechains with an electron transporting mobility reaching 10 -4 cm 2 V -1 s -1 . In order to further improve material performance, a detailed study is needed to understand the dependence of carrier transporting properties on both the core electronic structure and the sidechain. Here we present the detailed synthesis and characterization of a TP-TNI derivative bearing linear sidechains, which has demonstrated a field effect electron transport mobility up to 1.3×10 -3 cm 2 V -1 s -1 . The more than one order improvement of electron transport properties over the branched side chain homologue can be correlated to ordered twisted packing in the thin film, as revealed by in situ variable temperature grazing incidence wide-angle X-ray scattering (GIWAXS) studies. In-depth theoretical understanding of the frontier orbitals, reorganization energies and charge transfer integrals of TP-TNI molecules have provided further insight into the relationship between molecular stacking geometry and charge transporting properties.3

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Discotic Liquid Crystals

Cited by 666 publications

References 684 publications

Columnar self-assembly of N,N′,N′′-trihexylbenzene-1,3,5-tricarboxamides investigated by means of NMR spectroscopy and computational methods in solution and the solid state

Columnar self-assembly of N,N′,N′′-trihexylbenzene-1,3,5-tricarboxamides investigated by means of NMR spectroscopy and computational methods in solution and the solid state

Mesogenic complementary absorbing dyads based on porphyrin and perylene units

Understanding Electron Transport in Disk-Shaped Triphenylene-Tris(naphthaleneimidazole)s through Structural Modification and Theoretical Investigation

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