156244-98-3

Usage

Molecular structure

composed of three benzene rings linked together

Functional groups

contains five hexyloxy groups and one hydroxy group

Classification

triphenylene derivative

Uses

commonly used in organic synthesis and material science

Applications

development of liquid crystals, organic semiconductors, and other advanced materials

Versatility

structure and functional groups make it a useful building block in the design of new chemical and material compositions.

Upstream product

• 70351-86-9 2,3,6,7,10,11-hexakis(hexyloxy)triphenylene 
• 31189-03-4 2-(hexyloxy)phenol 
• 94259-20-8 1,2-dihexyloxybenzene 
• 120-80-9 benzene-1,2-diol 
• 111-25-1 1-bromo-hexane 

Relevant academic research and scientific papers

A convenient one-step reaction leading to a key discotic intermediate: Mono-hydroxy-triphenylene at multi-gram scale

This work reveals a novel reaction route deviated from a Scholl coupling reaction with an interrogation into the mechanism. A catalytic function of FeCl3 in the presence of protons plays a key role in the new reaction. It was discovered that by increasing the quantity of reagent FeCl3 is able to shift the reaction product from a symmetrically hexa-substituted coupling one to a mono-hydrolysed coupling product. The discovery offers a chance to explore and understand the reaction mechanism further. The new reaction enables a convenient one-step synthesis of mono-hydroxy-penta-alkoxytriphenylene, a key discotic liquid crystal intermediate for organic electronic materials, from a simple 1,2-dialkoxybenzenes reactant at a yield up to 65%.

Discotic liquid crystal-functionalized gold nanorods: 2- and 3D self-assembly and macroscopic alignment as well as increased charge carrier mobility in hexagonal columnar liquid crystal hosts affected by molecular packing and π-π interactions

Gold nanorods functionalized with triphenylene-based discotic liquid crystal (LC) motifs show striking self-assembly behavior both on transmission electron microscopy (TEM) grids as well as in the bulk enforced by the π-π-stacking of triphenylene groups of adjacent nanorods. TEM images confirm that these discotic LC nanorods form ribbons of parallel-stacked nanorods several hundred nanometer long. The pursued silane conjugation approach to decorate the nanorods allows for the preparation of dispersions of the nanorods in the hexagonal columnar phases of parent discotic LCs, where the nanorods can be macroscopically aligned with almost 80% efficiency by a simple shearing protocol. Doping the parent host materials with about 1% by weight of the discotic LC-capped nanorods also reduces the lattice parameter and the intracolumnar packing, which gives rise to enhanced charge carrier mobility in these hosts as determined by time-of-flight measurements.

The first examples of discotic radicals: Columnar mesomorphism in spin-carrying triphenylenes

The synthesis, columnar behaviour and magnetic properties of the first examples of radical discotics are reported. These organic molecular systems with spin sources have been accomplished by covalently linking triphenylene with molecular radicals. The col

Improved synthesis of monohydroxytriphenylenes (MHTs) - Important precursors to discotic liquid crystal families

Monohydroxypentaalkoxytriphenylenes are important intermediates for elaboration into complex covalently linked discotic liquid crystal assemblies. An improved, simple synthetic protocol is described that gives rapid access to these precursors in a single step.

A room temperature discotic mesogenic dyad based-on triphenylene and pentaalkynylbenzene

A facile synthesis of a novel room temperature discotic mesogenic dyad based on triphenylene and pentaalkynylbenzene linked via flexible alkyl spacer is reported. The thermotropic liquid crystalline (LC) property of the compound was investigated by polarizing optical microscopy (POM), differential scanning calorimetry (DSC), and X-ray diffractometry (XRD). The LC property of the dyad was further manipulated by preparing charge transfer (CT) complexes with trinitrofluorenone (TNF). The compound self-assembles into a columnar hexagonal mesophase and exhibits an excellent fluorescent emission property which has possible potential for various opto-electronic applications.

A convenient route to 2-(hydroxy)-3,6,7,10,11-penta-alkyloxytriphenylenes

Unsymmetrical monohydroxypentaalkoxytriphenylenes have been from the readily accessible symmetrical hexaalkyloxytriphenylenes using boron tribromide mediated ether cleavage.

Synthesis of monohydroxy-functionalized triphenylene discotics: green chemistry approach

This paper presents an environmentally benign procedure for the preparation of monohydroxy-functionalized triphenylenes using simple ionic reagents. Pyridinium hydrochloride, pyridinium hydrobromide, N-methyl pyridinium iodide, N-ethyl pyridinium bromide, and 1-n-butyl-3-methyl imidazolium bromide have been employed to prepare various monohydroxypentaalkoxytriphenylenes, which are valuable precursors for the synthesis of a variety of discotic monomers, dimers, oligomers, and polymers.

A new strategy towards the synthesis of a room-temperature discotic nematic liquid crystal employing triphenylene and pentaalkynylbenzene units

A new approach is reported for the design of a room-temperature discotic nematic (ND) liquid crystal (LC) dimer consisting of a triphenylene and a pentaalkynylbenzene unit linked via flexible alkyl spacers. The formation of the ND phase is realized most likely through folding of the dimeric molecule that prevent stacking between the triphenylene units, as suggested by modelling in the mesophase derived from X-ray scattering results and high-level DFT calculations.

Room temperature discotic liquid crystalline triphenylene-pentaalkynylbenzene dyads as an emitter in blue OLEDs and their charge transfer complexes with ambipolar charge transport behaviour

Six novel non-symmetric discotic liquid crystalline (DLC) dimers composed of pentaalkynylbenzene (PA) and triphenylene (TP) moieties were synthesized by using the CuI-Et3N catalyzed click reaction between terminal TP alkyne and PA azide. All the compounds exhibit mesomorphic behaviour at room temperature. Pure compounds 8a-b (n = 6, 8 & m = 1) and 9a-b (n = 6, 8 & m = 3) display a columnar centered rectangular (Colr) phase while 8c (n = 10, m = 1) and 9c (n = 10, m = 3) show a weak smectic (Sm) phase. Remarkably, the mesophase transforms from Colr and Sm to columnar hexagonal (Colh) on doping the pure compounds with electron-acceptor 2,4,7-trinitrofluorenone (TNF) molecules in a 2:1 TNF/compound ratio. The induction of stable Colh mesomorphism is driven through charge-transfer interactions of electron-rich PA and TP moieties with electron-acceptor TNF molecules. The thermal behaviour of the compounds was studied through polarised optical microscopy (POM), differential scanning calorimetry (DSC) and X-ray diffraction (XRD) studies. The performed grazing incidence small and wide angle X-ray scattering (GISAXS/GIWAXS) study showed good alignment ability of 9a in the Colr and complex 9a/TNF in the Colh phase. Additional information about the arrangement of molecules in the Colr and the Colh 2D lattice is deduced by the construction of electron density maps (EDM). The pure non-symmetric dimers 8a-c and 9a-c were blue luminescent in the solution state and shifted to green in the solid state because of aggregation. Hence, the fabrication of doped OLED devices by using 8a and 9a as an emitter with the configuration ITO/PEDOT:PSS/host:emitter/TPBi/LiF/Al illustrates the restoration of the electroluminescence (EL) spectrum to narrow and a blue shifted photoluminescence (PL) spectrum, which indicates the suppression of aggregates. Emitters 8a and 9a are doped with three different hosts: (carbazolyl)-1,1′-biphenyl (CBP), 4′,4′′-tri(N-carbazolyl)triphenylamine (TCTA) and 2,7-bis(carbazol-9-yl)-9,9-spirobifluorene (Spiro-2CBP), by varying the dopant concentration. The best EL performance is observed for the device fabricated with 8a (5 wt% in the CBP host) and 9a (3 wt% in the CBP host) with a maximum external quantum efficiency (EQE) of 2.1% and CIE coordinates of (0.16, 0.10). One of the studied complexes 8b/TNF exhibited an ambipolar charge carrier mobility of 1.78 × 10-3 cm2 V-1 s-1 and 1.25 × 10-3 cm2 V-1 s-1 for electrons and holes, respectively, at room temperature. The observed ambipolar mobility of the complex compound reveals its potential application as an organic semiconducting material.

TNF Induced Switching of Columnar Rectangular to Hexagonal Assemblies in a New Class of Triphenylene-Based Room Temperature Discotic Liquid Crystals

A straightforward synthesis of triphenylene-based oligomeric systems that self-organize into room temperature columnar structures is presented. The compounds with longer spacer length (m = 10 and 12) exhibit columnar rectangular (Colr) mesophase whereas the compound with m = 8 exists in glassy Colr state. Interestingly, the Colr self-assembly of these compounds switches to columnar hexagonal (Colh) on doping the compounds with 2,4,7-trinitrofluorenone (TNF). For the dopant concentration of 1:1 with respect to native compound, an intermediate transition state between Colr and Colh phase was observed which completely transformed into the hexagonal phase on increasing the concentration to 1:2 (compound: TNF) and afterward. Both the Colr and Colh self-assemblies have been well resolved by detailed X-ray analysis. These kind of oligomeric compounds generally possess a combination of desirable alignment properties analogous to monomeric compounds and long-lived glassy states similar to that of polymeric mesogens. In addition, charge hopping behavior is expected to increase in these compounds due to donor-acceptor interactions. Overall, these compounds can find possible potential applications in semiconductor devices.