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Chemical Structure| 121239-75-6 Chemical Structure| 121239-75-6

Structure of 121239-75-6

Chemical Structure| 121239-75-6

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Product Citations

Product Citations      Show More

Hyukmin Kweon ; Seonkwon Kim ; Borina Ha ; Seunghan Lee ; Soyeon Lee ; SeungHwan Roh , et al.

Abstract: High-density displays are required for the development of virtual and augmented reality devices. However, increasing the pixel resolution can lead to higher electrical pixel crosstalk, primarily due to a shared hole transport layer. Here we show that a silicone-integrated small-molecule hole transport layer can be patterned at the wafer scale with microlithography to mitigate electrical pixel crosstalk. This provides high-density pixelation and improved performance of the hole transport layer itself. With this approach, we create high-fdelity micro-pattern arrays with a resolution of up to 10,062 pixels per inch on a six-inch wafer. The silicone-integrated small-molecule hole transport layer can efectively modulate charge balance within the emission layers, improving the luminance characteristics of organic light-emitting diodes. We also show that organic light-emitting diodes integrated with micro-patterned silicone-integrated small-molecule hole transport layers have a reduced electrical pixel crosstalk compared with organic light-emitting diodes with a typical hole transport layer.

Purchased from AmBeed:

Amirreza Tarafdar ; Wenhua Lin ; Ali Naderi ; Xinlu Wang ; Kun (Kelvin) Fu ; Ian D. Hosein , et al.

Abstract: UV-induced frontal polymerization is an emergent rapid curing method for thermoset resin and its fiber composites which features the generation of a self-sustaining front that propagates within the entire material. This is different from using the commercially available UV curable resin which prohibited the curing of thermoset composites with opaque fibers (e.g., carbon fiber) due to the UV light being blocked by the fibers. In this study, we experimentally demonstrate that using the UV-induced frontal polymerization allows us to reduce the curing time of a standard tensile specimen of from traditionally 15 h using the oven curing method to only less than 1.5 min. The frontal polymerized specimens showed comparable and even superior tensile and flexural properties when compared to the traditional oven cured specimens. Moreover, we experimentally investigated the influence of the weight content of the photoinitiator, the UV light intensity, and the specimen geometry on the characteristics of the frontal polymerization process (i.e., front temperature, front velocity, and degree of cure) and the resulting tensile and flexural properties. The results and discussions are expected to provide guidance in scaling up this UV-induced frontal polymerization technique for the sustainable and additive manufacturing and repair of thermoset resin and its fiber composites.

Keywords: Frontal polymerization ; ; Sustainable manufacturing ; Out-of-oven curing ; Mechanical properties

Purchased from AmBeed:

Daniel P. Gary ; Md Abdullah Al Mahmud ; Madison G. Dawson ; John A. Pojman ;

Abstract: Frontal polymerization is a process in which a localized reaction zone propagates through the coupling of thermal transport and the Arrhenius kinetics of exothermic polymerization. Most that have been used produce volatile by-products, which create bubbles and voids. Tetraalkyl ammonium persulfates have been used but these require synthesis and do not have long shelf lives. A charge transfer complex (CTC) composed of an iodonium salt, and a phosphine compound has been identified as a gas-free initiator for free-radical thermal frontal polymerization. This CTC has (DMAPDP) as the donor and as the acceptor (IOC-8). The CTC was tested with several acrylates, and all were found to support bubble-free fronts. We determined the CTC mole ratio for some monomers at which the front velocity reaches a plateau.

Purchased from AmBeed: ;

Brecklyn R. Groce ; Emma E. Lane ; Daniel P. Gary ; Douglas T. Ngo ; Dylan T. Ngo ; Fahima Shaon , et al.

Abstract: Addition of fillers to formulations can generate composites with improved mechanical properties and lower the overall cost through a reduction of chemicals needed. In this study, fillers were added to resin systems consisting of epoxies and vinyl ethers that frontally polymerized through a radical-induced cationic frontal polymerization (RICFP) mechanism. Different clays, along with inert fumed silica, were added to increase the viscosity and reduce the convection, results of which did not follow many trends present in free-radical frontal polymerization. The clays were found to reduce the front velocity of RICFP systems overall compared to systems with only fumed silica. It is hypothesized that chemical effects and water content produce this reduction when clays are added to the cationic system. Mechanical and thermal properties of composites were studied, along with filler dispersion in the cured material. Drying the clays in an oven increased the front velocity. Comparing thermally insulating wood flour to thermally conducting carbon fibers, we observed that the carbon fibers resulted in an increase in front velocity, while the wood flour reduced the front velocity. Finally, it was shown that acid-treated montmorillonite K10 polymerizes RICFP systems containing vinyl ether even in the absence of an initiator, resulting in a short pot life.

Keywords: frontal polymerization ; cationic polymerization ; fillers ; clays ; minerals ; kinetics ; epoxies ; vinyl ethers

Purchased from AmBeed:

Do Hwan Kim ; Hyukmin Kweon ; Seonkwon Kim ; Borina Ha ; Seunghan Lee ; Soyeon Lee , et al.

Abstract: Ultrahigh-density displays are becoming increasingly prevalent in display technology for immersive digital interactive devices. However, the pursuit of higher pixel resolution has inadvertently led to the emergence of electrical pixel crosstalk, primarily due to the use of common hole transporting layers (HTLs). In this work, we present wafer-scale, anti-pixel crosstalk micro-lithography to mitigate electrical pixel crosstalk by incorporating a silicone-integrated small molecule HTL (SI-HTL), which not only enables ultrahigh-density pixelation but also enhances the functionality of the HTL itself. Leveraging the inherent silicon etching properties of SI-HTL, we successfully created high-fidelity micro-pattern arrays with a remarkable resolution of up to 10,062 pixels per inch on 6-inch wafer scales. Furthermore, SI-HTL effectively modulates charge balance within the emission layers, resulting in improved luminance characteristics in organic light-emitting diodes (OLEDs). Our comprehensive optical and quantitative assessment of electrical pixel crosstalk in OLEDs integrated with micro-patterned SI-HTL demonstrates the significant effectiveness of high pixelation of the HTL in alleviating the crosstalk issue.

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Muhammad Salman Malik ; Markus Wolfahrt ; Marco Sangermano ; Sandra Schlögl ;

Abstract: Radical induced cationic frontal polymerization (RICFP) is a promising route to achieve rapid curing of epoxy-based thermosets, requiring only a localized exposure with UV light. In the presence of a diaryliodonium-based photoinitiator and a thermal radical initiator, a self-sustaining hot front cures epoxide monomer via a cationic mechanism. However, the cationic polymerization of diglycidyl ether derivatives is slow (in comparison with other epoxides with higher reactivity) and, as a consequence, frontal polymerization is sluggish because the heat loss is not compensated by the rate of heat release. Cycloaliphatic epoxies possess a higher ring strain than diglycidyl ether derivatives and can be blended with the latter to increase its rate of frontal polymerization. In the current work, a comprehensive study on the influence of 3,4 epoxycyclohexylmethyl 3,4-epoxycyclohexane carboxylate (CE) on cure kinetics, viscosity, front velocity, mechanical, and thermo-mechanical properties of frontally cured bisphenol A diglycidyl ether derivatives is presented. The results show a direct relationship between frontal velocity and amount of reactive diluent while an inverse relationship with the storage viscosity is observed. It is found that increasing the content of cycloaliphatic epoxide reduces the glass transition but increases mechanical properties of frontally cured bisphenol A diglycidyl ether derivatives.

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Daniel P. Gary ; Douglas Ngo ; Amber Bui ; John A. Pojman ;

Abstract: Frontal polymerization is a process in which a localized reaction zone propagates from the coupling of thermal transport and the Arrhenius rate dependence of an exothermic polymerization; monomer is converted into polymer as the front passes through an unstirred medium. Herein we report the first study of charge transfer complexes (CTCs) as photo/thermal initiators for free-radical frontal polymerization. Front velocity was studied as a function of mole ratio between an aromatic amine, such as dimethyl-p-toluidine or dimethylaniline, and an iodonium salt. It was found that the front velocity reached a maximum at a certain mole ratio of amine to iodonium salt. The velocity remained constant upon increasing the ratio of amine to iodonium salt past this critical ratio. Fronts were also studied using N-phenyl glycine as an electron donor, but its utility was limited by low solubility. Lastly, the steric and electronic effects of the iodonium salt and counter anion were explored. It was found that CTCs using iodonium salts with less nucleophilic anions gave higher front velocities. In terms of intrinsic reactivity, the CTC composed of N,N-dimethyl-p-toluidine and bis[4-(tert-butyl)phenyl]iodonium tetra(nonafluoro-tert-butoxy)aluminate gave the highest front velocity per molal of iodonium salt.

Keywords: charge transfer complex ; free-radical polymerization ; frontal polymerization ; photoinitiator ; thermal initiator

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Gary, Daniel Paul ;

Abstract: Frontal polymerization (FP) is a process in which a front propagates in a localized reaction zone converting monomer into polymer. This work explored the kinetics and applications of FP for the development of cure-on-demand materials. The kinetic effects of fillers on frontal polymerization have not been thoroughly explored. In Chapter 2, various fillers were used, and their effects on front velocity and front temperature were determined. Clay minerals are primarily used, but the thermal conductive effects of milled carbon fiber were also explored. It was found that some fillers inhibit frontal polymerization through radical scavenging, while others increased the front velocity through thermal effects. Non-skid coatings are applied to the decks of marine vessels to provide both an anti-slip surface and corrosion protection. In Chapter 3, a base formulation for a one-component cure-ondemand coatings based on frontal polymerization was developed and studied. The coating is based on free-radical polymerization of acrylates and cures within minutes with the use of an infrared heater. In Chapter 4, the base formulation was applied as a non-skid coating engineered for a cure-to-service within minutes after cure initiation. The extended pot life and ability to selectively cure the coating will reduce waste, prevent error due to short working times, and improve operational availability by reducing the downtime from long cure-to-service times. The performance of the coating showed high value and potential application to marine vessels. Potential ways to improve the current non-skid coating are also discussed. Charge Transfer Complexes (CTCs) based on electron donor and acceptor interactions have been shown to act as dual thermal and photoinitiators. The first study done using charge transfer complexes as thermal initiators in frontal polymerization is presented in Chapter 5. xiv Various iodonium salts and amines were explored as electron acceptors and donors, respectively. The mole ratio of the iodonium salt to the amine, steric effects, and electronic effects were explored. It was found that the front velocity reached a maximum at a certain mole ratio of amine to iodonium salt. The relationship between the type of iodonium salt and front velocity was also explored. Chapter 6 concludes the work.

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Šebalj, Nikola ;

Abstract: With additive manufacturing, it is now possible to repeatedly create 3D objects without the need for molds or heavy machining. In comparison with other additive manufacturing techniques, vat photopolymerization provides a fast and precise way of producing complex shapes and objects. Photopolymerization 3D printing uses light exposure to solidify a resin formulation and is typically limited to a single material. In recent years, researchers have focused on using multi-material 3D printing to manufacture objects with heterogeneous properties. A promising approach for vat photopolymerization 3D printing of multi-material objects is the use of orthogonal photoreactions to tailor the network properties. In this work, three different hybrid acrylate-epoxide systems were formulated to present the possibility of preparing dual-curable resins for 3D printing, and tuning their properties using dual-wavelength DLP 3D printing technology: a) DOM:ECC = 75:25, 25:75 b) Eb:ECC = 25:75 c) PEGDA:ECC = 50:50 The 3D printer used in this work, employs two different light engines, operating at 405 and 365 nm. At visible light irradiation, a radical photoinitiator was selectively activated, leading to the curing of the acrylate component. Upon UV light exposure, a radical curing as well as cationic ring opening process of the epoxide component was initiated, yielding an interpenetrating network (IPN) with higher crosslinking density and stiffness. For the quantitative conversion of the epoxide network, a thermal post-baking step was carried out at 120°C for 2 hours. The cure kinetics of prepared hybrid acrylate-epoxide resins were investigated using the FTIR spectroscopy and through the initial printing trials. Selective illumination with either light source should shift material properties between the soft acrylate and rather stiff epoxide network. This was verified for DOM:ECC and PEGDA:ECC systems, while the system Eb:ECC displayed thermal instability and inability to print wavelength selective materials. The system Eb:ECC was not subjected to further testing. Furthermore, to investigate mechanical behavior of the printed samples, dynamical mechanical analysis and tensile test were carried out.

Keywords: DLP 3D printing ; dual-curable resins ; radical and cationic polymerization ; acrylate and epoxide ; mechanical properties

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Alternative Products

Product Details of [ 121239-75-6 ]

CAS No. :121239-75-6
Formula : C20H26F6IOSb
M.W : 645.07
SMILES Code : CCCCCCCCOC1=CC=C([I+]C2=CC=CC=C2)C=C1.F[Sb-](F)(F)(F)(F)F
MDL No. :MFCD08275318
InChI Key :QBOTYWKRKSTVOV-UHFFFAOYSA-H
Pubchem ID :21889414

Safety of [ 121239-75-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301+H331-H411
Precautionary Statements:P501-P261-P273-P270-P271-P264-P391-P301+P310+P330-P304+P340+P311-P403+P233-P405
Class:6.1
UN#:3467
Packing Group:

Computational Chemistry of [ 121239-75-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 29
Num. arom. heavy atoms 12
Fraction Csp3 0.4
Num. rotatable bonds 10
Num. H-bond acceptors 7.0
Num. H-bond donors 0.0
Molar Refractivity 111.09
TPSA ?

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

9.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.0
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

11.06
Log Po/w (WLOGP)?

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

7.6
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.

6.67
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

6.91
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

6.45

Water Solubility

Log S (ESOL):?

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

-10.45
Solubility 0.0000000227 mg/ml ; 0.0 mol/l
Class?

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

Insoluble
Log S (Ali)?

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

-11.22
Solubility 0.0000000039 mg/ml ; 0.0 mol/l
Class?

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

Insoluble
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

-8.74
Solubility 0.00000117 mg/ml ; 0.0000000018 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

Low
BBB permeant?

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

No
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

Yes
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

No
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

No
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

No
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.

-2.38 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

2.0
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

1.0
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.

0.17

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

2.0 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<3.0
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)

3.87
 

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[ 121239-75-6 ]

Chemical Structure| 121239-74-5

A1349682 [121239-74-5]

(4-(Octyloxy)phenyl)(phenyl)iodonium

Reason: Free-salt