150324-38-2

Upstream product

• 108-95-2 phenol 
• 103-90-2 4-acetaminophenol 
• 100-02-7 4-nitro-phenol 
• 30402-00-7 octyl-4-aminophenyl ether hydrochloride 
• 111-83-1 1-bromo-octane 
• 1689-82-3 4-hydroxyazobenzene 
• 49562-76-7 1-nitro-4-octyloxybenzene 
• 39905-45-8 4-octyloxyaniline 

Downstream Products

• 145121-43-3 [4-(10-Bromo-decyloxy)-phenyl]-(4-octyloxy-phenyl)-diazene 

Relevant academic research and scientific papers

A surfactant-encapsulated polyoxometalate complex towards a thermotropic liquid crystal

A novel surfactant-encapsulated terbium-substituted heteropolyoxotungstate complex [L1]13[Tb(SiW11O39)2] ·30H2O (SEC-1) bearing mesomorphous groups was successfully prepared by the ionic self-assembling route, exhibiting characteristic thermotropic liquid-crystalline behavior. The Royal Society of Chemistry 2005.

Dual photo-functionalized amphiphile for photo-reversible liquid crystal alignments

Without the conventional polymer-based liquid crystal (LC) alignment process, a newly synthesized dual photo-functionalized amphiphile (abbreviated as ADMA1) was successfully applied as a robust photo-reversible LC alignment layer by self-assembly and photo-polymerization. The LC alignment layer constructed by directly adding dual photo-functionalized amphiphiles into LC media significantly cuts the manufacturing cost as well as opens new doors for the fabrication of novel electro-optical devices.

Photoresponsive ionic liquid crystals based on azobenzene guanidinium salts

The use of non-ionic LC phases as anisotropic matrices for E/Z-isomerization of azo-guest molecules is often restricted due to limited solubilities and demixing effects. In this study we therefore employed an ionic liquid crystal (ILC) matrix to follow the photo-induced E/Z-isomerization of ionic mesogenic azobenzene guanidinium guests. The latter were prepared from 4-hydroxy-4′-(octyloxy)azobenzene, which was first treated with N-(bromoalkyl)phthalimides to introduce the spacer with varying chain length. Removal of phthalimide and final reaction with a formamidinium salt linked the ionic head group to the photoisomerizable azobenzene unit. Investigation of the mesomorphic behaviour revealed for all azobenzene ILCs smectic A mesophases with high translational order parameters and partial bilayers, as could be stated by layer spacing d. Similar packing behaviour was found for the solid state by X-ray crystal structure analysis. E/Z-isomerization of azobenzene ILCs which were completely miscible with the ionic LC phase of C12MIM-Br as anisotropic host was induced by irradiation with UV light and the reisomerization observed by time-resolved UV-Vis spectroscopy. For comparison, water was used as isotropic host. Z/E-reisomerization activation energies exhibited similar values of 97-100 kJ mol-1 irrespective of spacer lengths and the type of host. The results demonstrate that a proper match of steric requirements of host and guest as well as layer spacings are needed for a decreased activation energy. This journal is

Thermal- and photo-induced phase-transition behaviors of a tapered dendritic liquid crystal with photochromic azobenzene mesogens and a bicyclic chiral center

A ribbon-shaped chiral liquid crystalline (LC) dendrimer with photochromic azobenzene mesogens and an isosorbide chiral center (abbreviated as AZ 3DLC) was successfully synthesized and its major phase transitions were studied by using differential scanning calorimetry (DSC) and linear polarized optical microscopy (POM). Its ordered structures at different temperatures were further identified through structure-sensitive diffraction techniques. Based on the experimental results, it was found that the AZ 3DLC molecule exhibited the low-ordered chiral smectic (Sm*) LC phase with 6.31nm periodicity at a high-temperature phase region. AZ 3DLC showed the reversible photoisomerization in both organic solvents and nematic (N) LC media. As a chiral-inducing agent, it exhibited a good solubility, a high helical-twisting power, and a large change in the helical-twisting power due to its photochemical isomerization in the commercially available N LC hosts. Therefore, we were able to reversibly "remote-control" the colors in the whole visible region by finely tuning the helical pitch of the spontaneously formed helical superstructures. Remote-controlled color: A ribbon-shaped chiral dendritic liquid crystal was newly synthesized, and its thermal and photo-induced phase behaviors were investigated with the combined techniques of the thermal, microscopic, and scattering methods (see figure).

Photoresponsive behavior of hydrophilic/hydrophobic-based novel azobenzene mesogens: Synthesis, characterization and their application in optical storage devices

Three series of alkoxy chain-bearing azobenzene-derived quaternary ammonium iodides with an alkoxy chain at one end, namely N,N-diethanol-6-(4-((4′-alkyloxyphenyl)diazenyl)phenoxy)hexan-1-ammonium iodides, N-ethyl-N-ethanol-6-(4-((4′-alkyloxyphenyl)diazenyl)phenoxy)hexan-1-ammonium iodides and N,N-diethyl-6-(4-((4′-alkyloxyphenyl)diazenyl)phenoxy)hexan-1-ammonium iodides were synthesized and characterized. Their mesomorphic and photoswitching properties were examined via polarising optical microscopy (POM), differential scanning calorimetry (DSC) and UV-vis spectrophotometry. The liquid crystalline tilted schlieren texture of smectic C, non-tilted natural focal conic texture of smectic A and smectic B phases were observed in the N,N-diethanol- and N-ethyl-N-ethanol-bearing ammonium group substituted at the terminal via the alkoxy chain of the azo moiety. In these azo moieties, the equilibrium time for trans-cis isomerization was about 1 min and cis-trans isomerization occurred at around 590 min, which had the highest alkoxy chain and no hydroxyl group on their head group. The absence of a hydroxyl group on the terminal head group resulted in slow thermal back relaxation, whereas the hydroxyl group-bearing head group showed fast thermal back relaxation. These results suggest that the influence of the substituent on the cationic ammonium head group and alkoxy chain length on the photoisomerization of the azo compounds is vital for optical storage devices. Furthermore, the device fabricated using these materials demonstrated that they are excellent candidates for optical image storage applications.

Preparation method and application of sulfate type photoresponsive foam control agent

The invention discloses a preparation method and an application of a sulfate type photoresponsive foam control agent. The preparation method comprises the following steps: (1) reacting p-nitrophenol,potassium hydroxide and water to obtain p-hydroxyazobenz

AZOBENZENE COMPOUND AND HEAT PUMP SYSTEM USING THE SAME

PROBLEM TO BE SOLVED: To provide an azobenzene compound capable of repeated structural changes without heating, and a heat pump system using the same. SOLUTION: An azobenzene compound represented by the general formula (1) and undergoing cis-trans isomerization reaction upon light irradiation is used as a heat medium of a heat pump system. In the formula, at least one of R1 to R3 is (CH2CH2O)n-R10; R4 is R11, O-R11, NH-R11, or COO-R11; X- is Cl-, Br-, I-, BF4-, PF6-, CH3(CH2)nSO3-, TsO-, (YSO2)2 N-, or (NC)2 N-; n is an integer between 0 and 2; and Y is F, CF3, or C2F5. COPYRIGHT: (C)2015,JPO&INPIT

Photoliquefiable ionic crystals: A phase crossover approach for photon energy storage materials with functional multiplicity

Ionic crystals (ICs) of the azobenzene derivatives show photoinduced IC-ionic liquid (IL) phase transition (photoliquefaction) upon UV-irradiation, and the resulting cis-azobenzene ILs are reversibly photocrystallized by illumination with visible light. The photoliquefaction of ICs is accompanied by a significant increase in ionic conductivity at ambient temperature. The photoliquefaction also brings the azobenzene ICs further significance as photon energy storage materials. The cis-IL shows thermally induced crystallization to the trans-IC phase. This transition is accompanied by exothermic peaks with a total ΔH of 97.1 kJmol-1, which is almost double the conformational energy stored in cisazobenzene chromophores. Thus, the integration of photoresponsive ILs and self-assembly pushes the limit of solar thermal batteries.

Phototunable liquid-crystalline phases made of nanoparticles

The properties of liquid-crystalline (LC) hybrid systems made of inorganic nanoparticles grafted with photosensitive azo compounds are presented. For materials with a large density of azo ligands at the surface, the LC structure can be reversibly melted by UV light, and the return to the LC state does not require the absorption of visible light. For systems with a lower density of azo ligands, UV light causes shortening of the distance between metal sublayers in the lamellar phase. Interestingly, the azo derivatives attached to the nanoparticle surface show very different kinetics of cis/trans conformational change as compared to the free molecules. The cis form of free ligands in solution is stable for days, whereas the isomerization of molecules attached to the nanoparticle surface to the trans form takes only a few minutes. Apparently, owing to the crowded environment, azo ligands immobilized at a metal surface behave as they would in the condensed state.

Rational design, syntheses, characterization and solution behavior of amphiphilic azobenzene-containing linear-dendritic block copolymers

In this paper, based on the synthesis of precursor linear-dendritic block copolymers (LDBCs) with a linear poly(ethylene glycol) (PEG) block of molecular weight around 2000 and dendritic polyamidoamine (PAMAM) segments of generation G0 to G3, a series of azobenzene-containing amphiphilic LDBCs mPEG-dendr[PAMAM-(AZO)n] (n = 2, 4, 8, 16) have been successfully prepared in moderate yields 45-60%, through complete Michael addition between the peripheral amine groups of dendritic segment and the reactive azobenzene acrylate mesogen units bearing octyloxy tails and flexible decylmethylene spacers. The purified copolymers have been characterized and confirmed by NMR, FT-IR, MALDI-TOF MS, and GPC showing narrow molecular weight distribution in the range 1.09-1.20. A generation-dependent polymeric micellar aggregation behavior of thus obtained amphiphilic LDBCs from nanofibers of uniform diameter around 20 nm to nanospheres/oval sheets, vesicles, and porous large compound micelles (LCMs) of micrometer size has been demonstrated in selective solvent mixture of dioxane/water. Furthermore, photoisomerization transformation of these azobenzene-containing LDBCs and their kinetics of reversible trans-cis-trans photochemical transitions in THF solution have also been investigated, the measured trans-cis photoisomerization rate constant 0.0240 s-1 for G3 copolymer is twice of the 0.0127 s-1 determined for the precursor azobenzene compound, manifesting a kind of promising photoresponsive copolymer materials.