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Chemical Structure| 15155-41-6 Chemical Structure| 15155-41-6

Structure of 15155-41-6

Chemical Structure| 15155-41-6

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Nyakuchena, James ; Chiromo, Humphrey ; Radpour, Shahrzad ; Guckenburg, Josh ; Huang, Jier ;

Abstract: Emissive covalent organic frameworks (COFs) are a promising class of crystalline materials that have demonstrated applications for sensing and light-emitting diodes. However, white light emission from a single has not been achieved yet as it requires multicomponent organic chromophores that simultaneously emit blue, green, and red light. In this work, we report the successful synthesis of a single with efficient white light emission by utilizing tunable emission properties of 2,1,3- benzothiadazole after incorporating different functional groups on its core structure, which results in the formation of three ligands, i.e., 4′,4-(benzothiadiazole-4,7-diyl)-dibenzaldehyde (BTD), 4,4′-(benzoselenadiazole-4,7-diyl)-dibenzaldehyde (BSD), and 4,4′-(naphtho[2,3-c][1,2,3] selenadiazole-4,9-diyl)-dibenzaldehyde (NSD), that emit in the blue, green, and red regions of the visible light spectrum. We show that white light emission can only occur when BTD, BSD, and NSD are assembled in a single structure due to the facilitated energy transfer process from BTD to BSD/NSD. This work demonstrates a unique approach to developing new white light-emitting materials based on the structure.

Keywords: covalent ; organic ; framework ; emissive ; white ; light

Purchased from AmBeed: ; ; ;

Brian P. Radka ; Taewoo Lee ; Ivan I. Smalyukh ; Timothy J. White ;

Abstract: Polymer stabilized cholesteric liquid crystals (PSCLCs) are electrically reconfigurable reflective elements. Prior studies have hypothesized and indirectly confirmed that the electro-optic response of these composites is associated with the electrically mediated distortion of the stabilizing polymer network. The proposed mechanism is based on the retention of structural chirality in the polymer stabilizing network, which upon deformation is spatially distorted, which accordingly affects the pitch of the surrounding low molar-mass liquid crystal host. Here, we utilize fluorescent confocal polarized microscopy to directly assess the electro-optic response of PSCLCs. By utilizing dual fluorescent probes, sequential imaging experiments confirm that the periodicity of the polymer stabilizing network matches that of the low molar-mass liquid crystal host. Further, we isolate distinct ion-polymer interactions that manifest in certain photopolymerization conditions.

Purchased from AmBeed: ; ; ; ; ;

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

Purchased from AmBeed: ; ; ;

Alternative Products

Product Details of [ 15155-41-6 ]

CAS No. :15155-41-6
Formula : C6H2Br2N2S
M.W : 293.97
SMILES Code : BrC1=CC=C(C2=NSN=C12)Br
MDL No. :MFCD00658844
InChI Key :FEOWHLLJXAECMU-UHFFFAOYSA-N
Pubchem ID :626361

Safety of [ 15155-41-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301
Precautionary Statements:P264-P270-P301+P310+P330-P405-P501
Class:6.1
UN#:2811
Packing Group:

Computational Chemistry of [ 15155-41-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 9
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 52.82
TPSA ?

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

54.02 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.27
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

3.17
Log Po/w (WLOGP)?

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

3.22
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.

2.17
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

4.04
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.97

Water Solubility

Log S (ESOL):?

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

-4.27
Solubility 0.016 mg/ml ; 0.0000543 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.

-3.98
Solubility 0.0311 mg/ml ; 0.000106 mol/l
Class?

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

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

-4.29
Solubility 0.015 mg/ml ; 0.0000509 mol/l
Class?

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

Moderately 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

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.

-5.84 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

0.0
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

0.0
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<0.0
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)

1.97

Application In Synthesis of [ 15155-41-6 ]

* 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.

  • Upstream synthesis route of [ 15155-41-6 ]
  • Downstream synthetic route of [ 15155-41-6 ]

[ 15155-41-6 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 15155-41-6 ]
  • [ 1025451-57-3 ]
References: [1] Chemistry of Materials, 2012, vol. 24, # 21, p. 4123 - 4133.
[2] Journal of Materials Chemistry C, 2017, vol. 5, # 27, p. 6891 - 6898.
 

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Technical Information

Categories

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