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[ CAS No. 4286-55-9 ] {[proInfo.proName]}

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Chemical Structure| 4286-55-9
Chemical Structure| 4286-55-9
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Product Citations

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Lewis, Kristin L ; Hoang, Jonathan D ; Aye, Sarah S , et al. DOI:

Abstract: The directional deformation of liquid crystalline elastomers (LCEs) is predicated on alignment, enforced by variousprocessing techniques. Specifically, surface-aligned LCEs can exhibit higher temperature thermomechanical responses and weakenedstrain?temperature coupling in comparison to LCEs subjected to mechanical or rheological alignment. Recently, we reportedenhanced stimuli response of mechanically aligned LCEs containing supramolecular liquid crystals. Here, we prepare supramolecularLCEs via surface-enforced alignment to study the impact of the supramolecular bond strength and intermolecular forces. This wasevaluated using oxybenzoic acid (OBA) derivatives with and without pendant methyl groups as well as via oxybenzoic acid-pyridinecomplexes. Increased incorporation of supramolecular mesogens reduces the isotropic transition temperature and generally increasesthe strain?temperature coupling. The number of elastically active strands per unit volume, hydrogen bond conformations, andnetwork morphology are affected by the supramolecular mesogens and influence the observed stimuli response. Overall, reducedintermolecular interactions correlate with more desirable actuation properties, demonstrating the influence of the supramolecularmesogen’s structure.

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BRIAN P. RADKA ;

Abstract: Dynamic reconfiguration of optical materials has and continues to be of significant interestin technological utility in displays, healthcare, automotive, aerospace, and architecture. This thesis is concerned with so-called “polymer stabilized” cholesteric liquid crystals (PSCLCs), material systems in which application of an electric field can adjust the position or bandwidth of a selective reflection. These material systems are based upon the cholesteric liquid crystal (CLC) phase, which nascently self-organizes into a periodic helical structure in which refractive index modulation results in a polarization-specific Bragg reflection. Depending on material composition, application of an electric field to a CLC can result in reflection switching or “tuning” (e.g., shift in reflection wavelength) but typically these electro-optic responses are limited in magnitude or response time (often taking days for the reflection to recover). Comparatively, the integration of small concentrations of polymer, to “stabilize” the CLC phase, creates a material system that can undergo a dynamic and reversible electro-optic response. This thesis extends upon a number of prior examinations (generally focused on phenomena or functionality) undertaken at the Air Force Research Laboratory, that have demonstrated myriad responses including reflection bandwidth broadening, reflection wavelength tuning, and switching. The systematic investigations presented in this thesis directly elucidate the underlying electromechanical mechanism that is critical to enabling further optimization and enhancement of electro-optic response necessary for implementation in functional utility in applications. More specifically, the first aim of this thesis focuses on the formation and importance of the retention of structural chirality in the polymer stabilizing network (PSN) and the intermolecular interactions between the PSN and the non-reactive CLC host. Notably, PSCLCs prepared with non-liquid-crystalline polymer networks confirm that the chiral templating does not require the monomeric precursors to be liquid crystalline. Further, the cation-mediated electromechanical response of the deformation of the polymer network was correlated to be directly associated with the host (via distinctive confocal fluorescent experiments). The second aim of this thesis is focused on identifying and understanding the interactions between the polymer network and ions, through exploring the electrochemical properties in addition to the electro-optic response. The effect of polymerization on the electrical properties was investigated through impedance spectroscopy with mixtures prepared with metallic salts, ionic liquids, and ionic polymers. The electrical properties of these formulations were then correlated to the electro-optic response of PSCLCs prepared from them. Finally, informed by these fundamental studies, this thesis explored the molecular engineering of the polymer stabilizing network. This was achieved in two ways, both focused on affecting the crosslink density of the PSN. In the first, a dithiol additive was incorporated into the polymer network through copolymerization with the acrylate functionalized liquid crystalline monomer. This reaction decreases the crosslink density through both chain extension and chain transfer. Compositional studies isolated an optimum crosslink density/concentration to retain structural chirality with maximal elasticity. Second, a monofunctional liquid crystalline monomer was incorporated into the polymer network to decrease crosslink density while retaining high liquid crystalline character in the polymer network. The electromechanical mechanism in this material system enabled the realization of a new electro-optic phenomena in PSCLCs, reflection notch splitting

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Product Details of [ 4286-55-9 ]

CAS No. :4286-55-9 MDL No. :MFCD00002983
Formula : C6H13BrO Boiling Point : -
Linear Structure Formula :- InChI Key :FCMCSZXRVWDVAW-UHFFFAOYSA-N
M.W : 181.07 Pubchem ID :77970
Synonyms :
Chemical Name :6-Bromohexan-1-ol

Calculated chemistry of [ 4286-55-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 5
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 39.99
TPSA : 20.23 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.2
Log Po/w (XLOGP3) : 1.73
Log Po/w (WLOGP) : 1.93
Log Po/w (MLOGP) : 2.06
Log Po/w (SILICOS-IT) : 1.93
Consensus Log Po/w : 1.97

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.72
Solubility : 3.43 mg/ml ; 0.0189 mol/l
Class : Very soluble
Log S (Ali) : -1.77
Solubility : 3.07 mg/ml ; 0.0169 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.58
Solubility : 0.471 mg/ml ; 0.0026 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.54

Safety of [ 4286-55-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4286-55-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 4286-55-9 ]

[ 4286-55-9 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 4286-55-9 ]
  • [ 57473-33-3 ]
  • 7-chloro-1-(6-hydroxyhexyl)imidazo<1,2-a>pyrimidin-5-one [ No CAS ]
  • 2
  • [ 4286-55-9 ]
  • [ 4877-80-9 ]
  • 2,3,6,7,10,11-hexakis(6-hydroxyhexyloxy)triphenylene [ No CAS ]
YieldReaction ConditionsOperation in experiment
78.5% With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 20h;Reflux; 2,3,6,7,10,11-Hexakis(6-hydroxyhexyloxy)triphenylene(1): 2,3,6,7,10,11-Hexahydroxytriphenylene hydrate (1 g,3.0 mmol) and K2CO3 (8.5 g, 61.6 mmol) were added to aflask containing dimethylformamide (DMF, 100 mL) andheated at 80 oC. A solution of 6-bromo-1-hexanol (5.5 g,30.8 mmol) in DMF (20 mL) was added dropwise to thereaction mixture, and the resulting mixture was refluxed for20 h. Then, the reaction mixture was cooled to room temperature,and ethyl acetate (100 mL) was added and stirred for30 min. Brine (20 mL) was added, and the organic layer wasseparated twice. The combined organic layer was dried overanhydrous MgSO4, and the solvent was evaporated underreduced pressure. The crude product was purified by silicacolumn chromatography. (CH2Cl2:MeOH = 13:2) Yield:2.18 g (78.5percent). 1H NMR (200 MHz, CDCl3) delta 1.45-1.73 (m,36H), 1.86-2.06 (m, 12H), 3.68 (t, J = 6.4 Hz, 12H), 4.24 (t,J = 6.2 Hz, 12H), 7.82 (s, 6H).
  • 3
  • [ 4286-55-9 ]
  • [ 83883-26-5 ]
  • 5
  • [ 4286-55-9 ]
  • [ 605-32-3 ]
  • hydroxyhexyloxyanthraquinone [ No CAS ]
  • 6
  • [ 6933-49-9 ]
  • [ 4286-55-9 ]
  • N-(6-hydroxyhexyl)-2-methoxycarbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide; In dimethyl sulfoxide; at 65℃; for 4h; 2.97 g (10 mmol) of <strong>[6933-49-9]2-methoxycarbazole</strong> and 150 mg of benzyltriethylammonium chloride were sequentially added to a single-necked flask.25 ml of dimethyl sulfoxide, 20 ml of saturated sodium hydroxide solution, and 1.57 ml (12 mmol) of 6-bromo-n-hexanol.The reaction was carried out at 65 C for 4 h under magnetic stirring.Add 100 ml of deionized water, 100 ml of ethyl acetate, separate the liquid, and wash the organic phase several times with water until the solution is neutral (usually 3 times).The organic phase was separated and dried over anhydrous sodium sulfate.The residue was separated on silica gel column chromatography (eluent: dichloromethane).Drying at 35 C for 24 h under vacuum to give a white solidN-(6-hydroxyhexyl)-<strong>[6933-49-9]2-methoxycarbazole</strong> 2.54 g, yield 90%.
90% With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide; In dimethyl sulfoxide; at 65℃; for 4h; 1.97 g (10 mmol) of methoxycarbazole was sequentially added to a one-necked flask.Benzyltriethylammonium chloride 150mg, dimethyl sulfoxide 20ml, saturated sodium hydroxide 15ml,1.57 ml (12 mmol) of 6-bromo-n-hexanol was reacted at 65 C for 4 h with magnetic stirring.Add 100 ml of deionized water, 100 ml of ethyl acetate, separate the liquid, and wash the organic phase several times with water until the solution is neutral (generally3 times),The organic layer was separated and dried over anhydrous sodium sulfate.The white solid N-(6-hydroxyhexyl)methoxycarbazole was isolated in 2.7 g, yield 90%.
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