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Chemical Structure| 37500-95-1 Chemical Structure| 37500-95-1

Structure of 37500-95-1

Chemical Structure| 37500-95-1

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Product Citations

Product Citations

Grzelak, Magdalena ; Kumar, Dharmendra ; Kochman, Michał Andrzej ; Morawiak, Maja ; Wiosna-Sałyga, Gabriela ; Kubas, Adam , et al.

Abstract: The capability of organic emitters to harvest triplet excitons via a thermally activated delayed fluorescence (TADF) process has opened a new era in organic optoelectronics. Nevertheless, low brightness, and consequently an insufficient roll-off ratio, constitutes a bottleneck for their practical applications in the domain of organic light-emitting diodes (OLEDs). To address this formidable challenge, we developed a new design of desymmetrized naphthalimide (NMI) featuring an annulated indole with a set of auxiliary donors on its periphery. Their perpendicular arrangement led to minimized HOMO–LUMO overlap, resulting in a low energy gap (ΔEST = 0.05–0.015 eV) and efficient TADF emission with a photoluminescence quantum yield (PLQY) ranging from 82.8% to 95.3%. Notably, the entire set of dyes (NMI-Ind-TBCBz, NMI-Ind-DMAc, NMI-Ind-PXZ, and NMI-Ind-PTZ) was utilized to fabricate TADF OLED devices, exhibiting yellow to red electroluminescence. Among them, red-emissive NMI-Ind-PTZ, containing as an electron-rich component, revealed predominant performance with a maximum external quantum efficiency (EQE) of 23.6%, accompanied by a persistent luminance of 38 000 cd m−2 . This results in a unique roll-off ratio (EQE10000 = 21.6%), delineating a straightforward path for their commercial use in lighting and display technologies.

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Product Details of [ 37500-95-1 ]

CAS No. :37500-95-1
Formula : C20H25N
M.W : 279.42
SMILES Code : CC(C)(C)C1=CC=C2NC3=C(C=C(C=C3)C(C)(C)C)C2=C1
MDL No. :MFCD03425849
InChI Key :OYFFSPILVQLRQA-UHFFFAOYSA-N
Pubchem ID :15469209

Safety of [ 37500-95-1 ]

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

Computational Chemistry of [ 37500-95-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 21
Num. arom. heavy atoms 13
Fraction Csp3 0.4
Num. rotatable bonds 2
Num. H-bond acceptors 0.0
Num. H-bond donors 1.0
Molar Refractivity 94.34
TPSA ?

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

15.79 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

3.45
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

6.73
Log Po/w (WLOGP)?

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

5.92
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.

4.81
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

6.11
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

5.4

Water Solubility

Log S (ESOL):?

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

-6.14
Solubility 0.000203 mg/ml ; 0.000000727 mol/l
Class?

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

Poorly soluble
Log S (Ali)?

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

-6.87
Solubility 0.000038 mg/ml ; 0.000000136 mol/l
Class?

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

Poorly 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

-7.38
Solubility 0.0000117 mg/ml ; 0.000000042 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

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

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.

-3.23 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

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.

0.55

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)

1.9

Application In Synthesis of [ 37500-95-1 ]

* 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 [ 37500-95-1 ]

[ 37500-95-1 ] Synthesis Path-Downstream   1~11

  • 2
  • [ 949586-26-9 ]
  • [ 37500-95-1 ]
  • [ 34907-53-4 ]
  • (C6H13N(C6H3N(C6H3C(CH3)3)2)BC6H2(CH3)3)2C6H2 [ No CAS ]
  • 3
  • [ 37500-95-1 ]
  • [ 57103-20-5 ]
  • [ 1256943-89-1 ]
  • 4
  • [ 37500-95-1 ]
  • [ 4181-20-8 ]
  • [ 1364259-11-9 ]
  • 6
  • [ 78385-26-9 ]
  • [ 37500-95-1 ]
  • [ 1505522-29-1 ]
  • 7
  • [ 37500-95-1 ]
  • [ 2050-48-8 ]
  • [ 1396165-20-0 ]
YieldReaction ConditionsOperation in experiment
58.21% To a solution of 3b (0.376g, 1.0mmol), 18-crown-6 (0.027g, 0.1mmol) and 3,6-di(tert-butyl)carbazole (0.68g, 2.4mmol) in DMPU (5mL) was added K2CO3 (0.55g, 4.0mmol). The reaction mixture was then purged with nitrogen for ten minutes before adding CuI (0.020g, 0.1mmol). The following procedure was similar to that used for 1a. Yield: 58.21%. M.p.:367-370C. 1H NMR (300MHz, CDCl3): delta (ppm) 8.26-8.23 (d, J=8.4Hz, 4H), 8.13 (s, 4H), 7.83-7.80 (d, J=8.4Hz, 2H), 7.50-7.43 (m, 8H), 1.46 (s, 36H). 13C NMR (75MHz, CDCl3): delta (ppm) 143.7, 142.8, 138.4, 137.9, 129.2, 126.2, 123.7, 123.6, 116.1, 108.8, 34.4, 31.6. MS (MALDI-TOF) [m/z]: calcd for C52H56N2O2S, 772.41; found, 772.5745. Anal. Calcd. for C52H56N2O2S (%): C, 80.79; H, 7.30; N 3.62; S, 4.15.found:C, 80.62; H, 7.38; N 3.67; S, 4.17.
  • 8
  • [ 10016-52-1 ]
  • [ 37500-95-1 ]
  • 2,8-bis(di(tert-butyl)carbazol-9-yl)oxygafluorene [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate; In toluene; for 24h;Inert atmosphere; 2,8-Dibromodibenzofuran (1) (0.5 g, 1.53 mmol), 3,6-di-tert-butyl-9H-carbazole (2) (1.30 g, 4.66 mmol), Pd(OAc)2 (0.02 g, 0.096 mmol), tri-tert-butylphosphine solution (1.0 M in toluene) (0.06 g, 0.29 mmol), potassium tert-butoxide (0.29 g, 3.02 mmol) and 20 ml of dry toluene were heated at 110 C for 24 h under nitrogen. After cooling, the reaction mixture was diluted with ethyl acetate and the organic phase was washed with water and brine. After being dried over NaSO4 and filtered, the solvent was removed and the residue was purified by column chromatography using nhexane/ ethylacetate (7:1) as an eluent and crystallized from the eluent mixture of solvents to obtain DBO as white solid (0.54 g, yield: 49percent); m.p. 155-156 C. 1H NMR (400 MHz, CDCl3, ppm): delta 8.10 (d, 3H, J 2.1 Hz, Ar), 8.02 (d, 1H, J 2.1 Hz, Ar), 7.85 (d, 1H, J 8.6 Hz, Ar), 7.68 (d, 1H, J 8.6 Hz, Ar), 7.60e7.50 (m, 3H, Ar), 7.47-7.38 (m, 5H, Ar), 7.26e7.20 (m, 3H, Ar), 7.17 (s, 1H, Ar), 1.40 (s, 36H, 12 -CH3). 13C NMR (75.4 MHz, CDCl3, ppm): delta 156.9, 154.8, 142.8, 139.9, 133.1, 127.8, 126.3, 125.6, 123.9, 123.6, 123.1, 120.9, 119.4, 116.2, 112.7, 111.9, 109.1, 34.7, 32.1. MS (APCI, 20 V), m/z: 724 ([M+H]+). Elemental analysis: calcd (percent) for C52H54N2O: C 86.38, H 7.53, N 3.87, O 2.21; found C 86.43, H 7.54, N 3.81.
  • 11
  • [ 67515-59-7 ]
  • [ 37500-95-1 ]
  • 4-(3,6-di-tertbutyl-9H-carbazol-9-yl)-3-(trifluoromethyl)benzonitrile [ No CAS ]
 

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