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Chemical Structure| 40817-08-1

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Ng, Alicia ; Telles, Rodrigo ; Riley, Katherine S ; Lewis, Jennifer A ; Cook, Caitlyn C ; Lee, Elaine , et al.

Abstract: Cholesteric liquid crystal elastomers (CLCEs) hold great promise for mechanochromic applications in anti-counterfeiting, smart textiles, and soft robotics, thanks to the structural color and elasticity. While CLCEs are printed via direct ink writing (DIW) to fabricate free-standing films, complex 3D structures are not fabricated due to the opposing rheological properties necessary for cholesteric alignment and multilayer stacking. Here, 3D CLCE structures are realized by utilizing coaxial DIW to print a CLC ink within a silicone ink. By tailoring the ink compositions, and thus, the rheological properties, the cholesteric phase rapidly forms without an annealing step, while the silicone shell provides encapsulation and support to the CLCE core, allowing for layer-by-layer printing of self-supported 3D structures. As a demonstration, free-standing bistable thin-shell domes are printed. Color changes due to compressive and tensile stresses can be witnessed from the top and bottom of the inverted domes, respectively. When the domes are arranged in an array and inverted, they can snap back to their base state by uniaxial stretching, thereby functioning as mechanical sensors with memory. The additive manufacturing platform enables the rapid fabrication of 3D mechanochromic sensors thereby expanding the realm of potential applications for CLCEs.

Keywords: 3D architectures ; cholesteric liquid crystal elastomers ; core-shell ; direct ink writing ; mechanochromic ; passive sensing

Purchased from AmBeed: ;

Kim, Jong Bin ; Li, Shangsong ; Wang, Kun‐Yu ; Chi, Yinding ; Yang, Shu ;

Abstract: Materials that exhibit varied optical responses to different modes of mechanical stimuli are attractive for complex sensing and adaptive functionalities. However, most mechanochromic materials are fabricated from films or fibers with limited actuation modes. Here, hollow tubes of a symmetric sheath are created using cholesteric liquid crystal elastomers (CLCEs) at the sub-millimeter scale. The oligomeric precursor is sheared in an elastomeric microchannel to form uniform thickness, overcoming gravity effect and Plateau-Rayleigh instability. In addition, the coloration is achieved to be faster and have higher reflectivity compared to that of solid fibers. The tube can undergo axial, circumferential, and radial strains upon extension and inflation. The combination of molecular anisotropy and geometry of the tube enables highly sensitive mechanochromic responses in both azimuthal and axial directions: inflation causes red-to-violet shift (≈220 nm) at a circumferential strain of 0.57. The inflation of a bent tube generates another mechanochromic mode with a higher sensitivity to strain. Finally, display of 26 alphabets is achieved using 5 tubes, of which the positions can be reconfigured, and curvature-dependent 3D photonic skins are demonstrated from tubes wrapped around 3D objects. The multi-mode mechanochromic tubes will find applications for soft robotics, adaptive displays, wearable sensors, and spectrometers.

Keywords: cholesteric liquid crystal elastomers ; displays ; mechanochromism ; structural colors ; tube

Purchased from AmBeed:

Antonio Proctor Martinez ; Alicia Ng ; So Hee Nah ; Shu Yang ;

Abstract: Liquid crystal elastomers (LCEs) are promising candidates for creating adaptive textile-based devices that can actively and reversibly respond to the environment for sensing and communication. Despite recent advances in scalable manufacturing of LCE filaments for textile engineering, the actuation modes of various LCE filaments focus on contractual deformations. In this study, manufacture of polydomain LCE filaments with potential scalability by wet-spinning is studied, followed by mechanical exploitation to program liquid crystal mesogen alignments, demonstrating both contractual and twisting actuation profiles. By plying these LCE filaments into yarns with different twist concentrations, yarn actuation, and mechanical performance is tuned. Yarns plied at 4 twists per cm can generate up to a seven-fold increase in elastic modulus while maintaining 90% of actuation strain performance from their native filament. The contractual and twisting LCE filaments are then embroidered with varying stitch types to spatially program complex 2D-to-3D transformations in “inactive” fabrics. It is shown that a running stitch can actuate up to 15% in strain and create angular displacements in fabric with twisted mesogen alignments. It is envisioned that the wet-spun polydomain LCE filaments for diverse plied yarn production together with textile engineering will open new opportunities to design smart textiles and soft robotics.

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Li, Shangsong ; Yu, Kun‐Hao ; Garcia, Isabel ; Nah, So Hee ; Chui, Hiu Ning Tiffany ; Tian, Ziting , et al.

Abstract: Direct ink writing (DIW) of core-shell structures allows for patterning hollow or composite structures for shape morphing and color displays. Cholesteric liquid crystal elastomers (CLCEs) with liquid crystal mesogens assembled in a helix superstructure are attractive for generating tunable iridescent structural colors. Here, by fine-tuning the rheology of the core and shell materials, respectively, this study creates droplets or a continuous filament in the core from the precursors of polydimethylsiloxane (PDMS) or , whereas CLCE forms the outer shell. By introducing a dye in the droplets, the skin structures of cephalopods, consisting of chromatophores and iridocytes, are mimicked for enhanced color saturation, lightness, and camouflage. After removal of the core material, a CLCE hollow fiber is obtained, which can switch colors upon mechanical stretching and pneumatic actuation, much like papilla along with iridocytes. Further, liquid crystal mesogens assembled in the bulk of the fiber are in polydomain. Thus, the skin appears opalescent at room temperature, much like how leucophores enhance reflectins. Upon heating above the nematic to isotropic transition temperature, the skin becomes transparent. Lastly, a cephalopod model is constructed, where different parts of the model can change colors independently based on different mechanisms.

Keywords: camouflage ; cholesteric liquid crystal elastomer ; core-shell fiber ; direct ink writing ; structural colors

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Liu, Yuan ; Kannan, Kurunthachalam ;

Abstract: (LCMs) are biphenyl- or cyclohexane-basedorganic chemicals used in electronic digital displays, and several of them possessbioaccumulative and toxic properties. Little is known about their occurrence in indoordust from the United States. We analyzed 60 LCMs in 104 residential indoor dustsamples collected from 16 states across the United States. Forty-seven of 60 LCMswere detected in dust samples at a median ∑LCM concentration of 402 ng/g (range:not detected to 4300 ng/g). Trans-4-propylcyclohexyl trans,trans-4’-propylbicyclohexyl-4-carboxylate (MPVBC) and (trans,trans)-4-fluorophenyl 4’-pentyl-[1,1’-bi-(cyclohexane)]-4-carboxylate (FPeBC) were frequently detected in dust samples. Weinvestigated potential sources of LCMs in dust by determining concentrations andprofiles of these chemicals in smartphone screens, desktop and laptop computermonitors, and displays of other electronic devices and found that profiles insmartphones matched closely with those found in dust. The calculated median dailyintake of ∑LCM through dust ingestion was 1.19 ng/kg bw/d for children, whereas that through dermal absorption was 0.18 ng/kgbw/d for adults in the United States.

Keywords: liquid crystal monomers ; dust ; exposure ; digital displays ; LCD

Purchased from AmBeed: ; ; ;

Ning, Yifan ; Liu, Zhe ; Yang, Shengsong ; Morimitsu, Yuma ; Osuji, Chinedum O. ; Murray, Christopher B.

Abstract: Liquid crystal-nanoparticle (LC-NP) hybrid systems allow synergistic interactions between LC matrixes with anisotropic alignment and NP dopants with versatile functionalities. A uniform, well-dispersed, and highly stable thermotropic LC-NP mixture paves the way for further applications. In this work, a linear promesogenic ligand and two types of dendritic promesogenic ligands with alkyl or oligo ethylene glycol (OEG) chains are designed and synthesized to facilitate incorporating NPs into the thermotropic 4-cyano-4′-pentylbiphenyl (5CB) LC matrix. A comparison study between the linear and the dendritic ligands on the capability to promote miscibility and stability of NPs in LCs is conducted. Miscibility test results show that the linear ligand and the OEG-chained dendrimer both perform well in uniformly dispersing NPs in LCs. Dynamic assemblies of NPs assisted by dendritic ligands and driven by aligning and equilibrating of mesogens are captured, showing the potential of manipulating the assembly of NPs through external thermal stimuli. The stability test shows that both types of dendrimers can significantly enhance the shelf-life time and thermal stability of NPs compared to the linear ligand. In particular, Au NPs capped with OEG-chained dendrimers are stable in 5CB for 6 mo at room temperature and over 10 h at 50 °C. The synthesis of dendritic ligands is highly modulated and can be generalized onto NPs with different dimensions and properties. Tied by the dendritic promesogenic ligands, this LC-NP hybrid system with good uniformity and stability could be further applied to tunable optical displays, responsive materials, etc.

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Alternative Products

Product Details of [ 40817-08-1 ]

CAS No. :40817-08-1
Formula : C18H19N
M.W : 249.35
SMILES Code : N#CC1=CC=C(C2=CC=C(CCCCC)C=C2)C=C1
MDL No. :MFCD00036350

Safety of [ 40817-08-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 40817-08-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 19
Num. arom. heavy atoms 12
Fraction Csp3 0.28
Num. rotatable bonds 5
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 80.79
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

23.79 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

3.43
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

5.42
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

4.96
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

4.25
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

5.49
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.71

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-4.94
Solubility 0.00288 mg/ml ; 0.0000115 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-5.68
Solubility 0.000527 mg/ml ; 0.00000211 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-7.01
Solubility 0.0000243 mg/ml ; 0.0000000973 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

Yes
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

Yes
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-3.97 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

1.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<2.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.23
 

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