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InChI:InChI=1/C16H25NO2/c1-3-4-5-6-7-8-13-19-16-11-9-15(10-12-16)17-14(2)18/h9-12H,3-8,13H2,1-2H3,(H,17,18)

Upstream product

• 111-83-1 1-bromo-octane 
• 103-90-2 4-acetaminophenol 

Downstream Products

• 30402-00-7 octyl-4-aminophenyl ether hydrochloride 
• 39905-45-8 4-octyloxyaniline 
• 317351-87-4 (C₈H₁₇OC₆H₄NCH)2 
• 317351-88-5 C₃₂H₄₈N₂O₂ 
• 1146964-39-7 N-[3-bromo-4-(octyloxy)phenyl]acetamide 
• 1396273-31-6 4-{(E)-[(4-octyloxyphenyl)imino]methyl}phenyl thiophene-3-carboxylate 
• 1354641-61-4 4-[10-(acryloyloxy)decyloxy]-4'-octyloxyazobenzene 
• 1354641-60-3 4-(10-hydroxydecyloxy)-4'-octyloxyazobenzene 
• 1263036-79-8 2,5-bis[(4-octyloxyphenyl)aminocarbonyl]styrene 

Relevant academic research and scientific papers

Synthesis, liquid crystalline properties and photo switching properties of coumarin-azo bearing aliphatic chains: Application in optical storage devices

A series of novel azo-coumarin derivatives with different aliphatic chain length (3a-e) have been synthesized and characterized for liquid crystal properties and their photoswitching behavior. The incorporation of coumarin along with azobenzene was prepared via esterification reaction and differ in the length of alkyl group, CnH2n+1, where n = 6, 8, 10, 12 and 14. Azo-coumarin bearing C14 alkyl chain shows Smectic–A phase while azo-coumarin bearing rest of long alkyl chain exhibited Nematic phase. The incorporation of natural product moieties into azobenzene network has increased electron delocalisation and liquid crystal properties. The photoswitching properties of said molecules were tested and the coumarin-azo compounds 3a-e took ~46 s to reach photostationary state during UV illumination and exhibited long thermal back relaxation time (~16 h) in solutions. Device is also fabricated to see the performance of the device with respect to the alkyl chain length. Presented studies show the importance of azo-coumarin derivatives with different chain length for the application of optical storage devices.

New long-chain donor-acceptor-donor pyromellitic diimide (PMDI) derivatives. A combined theoretical and experimental study

This study involves the electrochemical, thermal and photophysical profiling of new pyromellitic diimide (PMDI) derivatives containing alkyl chains of different sizes. The photophysical investigation shows that all compounds exhibited absorption in the UV-B region (～290 nm). The band-gaps were calculated by onset peak values of around 4.03 eV. The compounds are photoactive in the UV-A region (312–328 nm) with a small solvatochromic effect in the excited state (Δλem = 16 nm). The electrochemical studies revealed that the reduction of the bisimide moiety showed two waves due to the formation of both the radical anion and a dianion. On the other hand, oxidation showed two waves due to the formation of radical cations and dications. The thermal properties were measured by differential thermal analysis (DTA) and thermogravimetric analysis (TGA), and the materials showed high thermal stability (Td > 300 °C). Theoretical calculations were also performed to study the geometry and charge distribution of these compounds in their ground and excited electronic states. No significant changes in the absorption and emission maxima were found by changing the solvent or substituents attached to the PMDI structure.

Columnar self-assembly of bowl shaped fluorescent liquid crystals based on calix[4]arene with Schiff base units

A new family of bowl-shaped molecules with a calix[4]arene rigid core and appended on four-sides, that display a wide range of hexagonal columnar phases, has been synthesised and well characterized. The thermal behaviours of the present compounds were established using a combination of polarising optical microscopy (POM), differential scanning calorimetry (DSC) and a high-temperature powder X-ray diffraction method (XRD). It is found that all of the synthesised materials show an enantiotropic hexagonal columnar liquid crystal phase. The structural and conformation characterization of these newly synthesised compounds was achieved by FT-IR, 1H NMR, and 13C NMR spectroscopy. All of the synthesised compounds exhibited good blue luminescence in solution under long wavelength UV light. To explore the structure property correlations, the alkoxy side chain group was varied from a lower alkyl spacer to a higher alkyl spacer on the lower rim of the calix[4]arene. The present research specified that the introduction of linking groups on the lower rim with an n-alkoxy side group is an influential approach to obtaining a supramolecular bowl shape liquid crystal which has good thermal and photophysical behaviour.

Synthesis and mesomorphic properties of 2,4-bis(4′-n-pentyloxybenzoyloxy)- benzylidine-4″- n-alkoxyaniline

The synthesis and mesomorphic properties of a new series of 2,4-bis(4′-npentyloxybenzoyloxy)- benzylidine-4″ -n-alkoxyaniline (DC5An) are reported. The molecular structure of compounds was confirmed by FTIR, 1H-NMR, 13C-NMR, mass spectroscopy and elemental analysis. The mesomorphic properties were studied by differential scanning calorimetry (DSC) and polarizing optical microscopy (POM) measurements. All compounds of the series exhibit nematic (N) and smectic C (SmC) phases. The first four homologues (DC5A1-DC5A4) display a N mesophase, whereas the highest homologues (DC5A5-DC5A10) exhibit an enantiotropic dimorphism N and SmC phases. The mesomorphic properties of the present series are compared and discussed with other structurally related series.

Photosensitive self-assembling materials as functional dopants for organic photovoltaic cells

New photosensitive liquid crystalline compounds with a specific molecular structure have been designed in order to use them as functional dopants for organic photovoltaic devices. The main idea is to establish the effect of doping on the bulk-heterojuncti

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.

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.

A molecular insight on the supramolecular assembly of thiophene polymers

Herein, the relationship between supramolecularly self-assembled microstructures and the chemical structures of photoluminescent molecules is discussed. A series of non-amphiphilic molecules with different length alkyl chains (4-14), central mesogenic groups, and chemical linkers were designed and synthesized. Intricate analysis shows that the supramolecular assembly varies with change in torsion angle of the thiophene linking group on elongation of the alkyl chain. Small angle X-ray scattering measurement shows long range molecular interaction for lower alkyl chain length, AFM reveals circular domains for octyl and decyl alkyl group polymers. UV-Visible and photoluminescence studies in solution and thin-film show that the J-aggregate patterns for the circular domain of the polymer backbone has a major effect on the polymer absorbance, and produces a larger shift for the photoluminescence signals at higher wavelengths. Excitation polarisation studies show a change in molecular ordering in various colour regions with change in aggregation by means of maximum dichroic ratio for the circular domain assembly. Charge carrier mobility and cyclic voltammetry studies show higher mobility and reduced band gap for these circular domain polymers. Dynamic light scattering studies of octyl alkyl chain polymers show a bimodal distribution, which shows the apparent nature of anisotropy in solution. The Royal Society of Chemistry.

Influences of hydrogen bonding and peripheral chain length on mesophase structures of mesogen-jacketed liquid crystalline polymers with amide side-chain linkages

A series of mesogen-jacketed liquid crystalline polymers, poly{2,5-bis[(4-alkoxyphenyl)aminocarbonyl]styrene} (P-Cm, where m is the number of carbon atoms in the alkoxy groups, and m = 1, 4, 8, 12), with an amide core and flexible tails of varying lengths on the two ends in the side chain were designed and successfully synthesized via conventional radical polymerization. The mesophase structures of these polymers were dependent on the number of carbon atoms in the peripheral chains. Wide-angle X-ray diffraction and polarized light microscopy results revealed that the polymers with m ≥ 4 could form smectic A phases, while a columnar nematic phase could be formed for the polymer with methoxy end groups (P-C1). The hydrogen bonding among the side-chain amide groups might play an important role in forming and stabilizing these liquid crystalline phases, which was suggested by the results from variable-temperature FTIR and 2D IR analyses.

Studies of calamitic liquid crystalline compounds involving ester-azo central linkages with a biphenyl moiety

Two mesogenic homologous series involving ester-azo central linkages with a biphenyl moiety have been synthesized, such as 4'-[(4-n-alkoxyphenyl)diazenyl] biphenyl-4-ol (series I) and 4'-[(4-n-alkoxyphenyl) diazenyl]-4-butoxy phenyl biphenyl-4-carboxylate (series II). Azobiphenyl of series I having a free hydroxyl group with strong hydrogen bonding exhibits a high-temperature enantiotropic smectic phase. Whereas in series II, compounds containing C 1-C8 carbon atoms exhibit only a monotropic smectic phase and compounds with C10, C12, C14, and C 16 atoms show an enantiotropic smectic phase. These compounds were characterized by elemental analysis, FT-IR, 1H-NMR, and mass spectral studies. The phase transition and mesogenicity of these substances were studied by polarizing optical microscopic and differential scanning calorimetric techniques. Their thermal stabilities and other characteristics are discussed. Copyright Taylor &Francis Group, LLC.