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Chemical Structure| 622-75-3 Chemical Structure| 622-75-3

Structure of 1,4-Phenylenediacetonitrile
CAS No.: 622-75-3

Chemical Structure| 622-75-3

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Product Citations

Product Citations

Pawlak, Mateusz ; Pierzchała, Adam ; Benchimol, Elie ; Tessarolo, Jacopo ; Rebholz, Lukas ; Krstić, Marjan , et al.

Abstract: Circularly polarized luminescence (CPL) in purely organic materials is limited by the almost exclusively electric nature of electronic transitions. Resolving this problem is possible through structuring organic materials at dimensions comparable to the wavelength of visible light. Here, the study explores the use of thin films made of chiral organic nanotubes for the enhanced induction of CPL. The study first performs multi-scale modeling of the chiroptical properties of organic nanotubes using the T-matrix method. Combined with chiroptical measurements, including Mueller matrix polarimetry, the study discusses the chiroptical properties of organic materials within the frames of their multi-scale structuring. When embedding aggregation-induced fluorogens (AIEgens) into the structured films, composites featured with gigantic glum factors reaching ≈10−1 are obtained. Importantly, a series of control experiments is performed to exclude common parasitic effects that can lead to the apparent CPL signals. The enhanced chiroptical properties of the composite films of organic nanotubes and AIEgens enable visual discrimination of their handedness both in the absorption and emission realms. The uncovered multi-mode enhancement of CPL directs future endeavors for anticounterfeiting or holography applications.

Keywords: aggregation-induced emission ; circular differential scattering ; organic luminophores ; supramolecular nanotubes ; thin films

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Alternative Products

Product Details of [ 622-75-3 ]

CAS No. :622-75-3
Formula : C10H8N2
M.W : 156.18
SMILES Code : N#CCC1=CC=C(CC#N)C=C1
MDL No. :MFCD00001923
InChI Key :FUQCKESKNZBNOG-UHFFFAOYSA-N
Pubchem ID :69327

Safety of [ 622-75-3 ]

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

Computational Chemistry of [ 622-75-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.2
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 45.49
TPSA ?

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

47.58 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.49
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

0.96
Log Po/w (WLOGP)?

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

1.82
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.

1.39
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

2.46
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.62

Water Solubility

Log S (ESOL):?

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

-1.65
Solubility 3.49 mg/ml ; 0.0223 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-1.55
Solubility 4.44 mg/ml ; 0.0284 mol/l
Class?

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

Very 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

-3.37
Solubility 0.0674 mg/ml ; 0.000432 mol/l
Class?

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

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

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.

-6.57 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

1.0
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<1.0
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)

1.0

Application In Synthesis of [ 622-75-3 ]

* 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 [ 622-75-3 ]

[ 622-75-3 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 622-75-3 ]
  • [ 204905-77-1 ]
  • [ 368421-24-3 ]
  • 2
  • [ 622-75-3 ]
  • [ 28785-06-0 ]
  • (2Z,2'Z)-2,2'-(1,4-phenylene)bis(3-(4-propylphenyl)acrylonitrile) [ No CAS ]
  • 3
  • [ 622-75-3 ]
  • [ 110677-45-7 ]
  • C48H30N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With potassium tert-butylate; tetra(n-butyl)ammonium hydroxide; In tetrahydrofuran; tert-butyl alcohol; at 46℃; for 0.5h;Inert atmosphere; Add 813.9mg of carbazole benzaldehyde and 234.3mg of p-phenylacetonitrile to a 50ml flask, add 10ml after evacuating nitrogen three timesThe solution of tert-butanol and 5ml of purified tetrahydrofuran was heated to 46 C with stirring, and a solution of 0.3mmol of potassium tert-butoxide in tetrahydrofuran and 0.2ml of tetrabutylammonium hydroxide were quickly injected for 30 minutes.After the reaction was completed, the system was poured into methanol acidified with acetic acid, filtered with suction, and separated by column chromatography with a yield of 68%.
 

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Technical Information

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