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Chemical Structure| 81-86-7 Chemical Structure| 81-86-7

Structure of 81-86-7

Chemical Structure| 81-86-7

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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 [ 81-86-7 ]

CAS No. :81-86-7
Formula : C12H5BrO3
M.W : 277.07
SMILES Code : O=C(C1=CC=CC2=C(Br)C=CC3=C12)OC3=O
MDL No. :MFCD00006927
InChI Key :DTUOTSLAFJCQHN-UHFFFAOYSA-N
Pubchem ID :66493

Safety of [ 81-86-7 ]

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

Computational Chemistry of [ 81-86-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 16
Num. arom. heavy atoms 10
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 61.39
TPSA ?

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

43.37 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.87
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

3.23
Log Po/w (WLOGP)?

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

2.91
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.

3.32
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

3.52
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.

-4.06
Solubility 0.0244 mg/ml ; 0.0000881 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.

-3.81
Solubility 0.0425 mg/ml ; 0.000154 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

-4.99
Solubility 0.00282 mg/ml ; 0.0000102 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

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.

-5.7 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

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<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)

2.08

Application In Synthesis of [ 81-86-7 ]

* 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 [ 81-86-7 ]

[ 81-86-7 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 67-56-1 ]
  • [ 81-86-7 ]
  • [ 35615-97-5 ]
  • [ 59866-97-6 ]
  • 2
  • [ 81-86-7 ]
  • [ 15424-38-1 ]
  • 4-(phenyl anthracen-9-yl)amino-1,8-naphthalic anhydride [ No CAS ]
  • 3
  • [ 81-86-7 ]
  • 9,9-diethyl-N,N-diphenyl-7-vinyl-9H-fluoren-2-amine [ No CAS ]
  • [ 68176-57-8 ]
  • 11-tert-butyl-(E)-4-(2-(7-(diphenylamino)-9,9-diethyl-9H-fluoren-2-yl)vinyl)-7H-benzimidazo[2,1-a]benzo[de]isoquinolin-7-one [ No CAS ]
  • 11-tert-butyl-(E)-3-(2-(7-(diphenylamino)-9,9-diethyl-9H-fluoren-2-yl)vinyl)-7H-benzimidazo[2,1-a]benzo[de]isoquinolin-7-one [ No CAS ]
  • C53H45N3O [ No CAS ]
  • C53H45N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
15.2%; 17.0% A flask was charged with a mixture of 6 (0.94 g, 2.16 mmol), 8 (1.07 g, 2.59 mmol), Pd(OAc)2 (1.0 mg, 0.043 mmol), P(o-tolyl)3 (0.026 g, 0.086 mmol), triethylamine (1.53 g, 15.12 mmol) and DMF (30 mL). The reaction mixture was heated at 90 °C for 24 h under N2. After cooled to room temperature, the mixture was poured into water (200 mL), and the red solid was collected, washed with waterand dried in vacuo. The crude product was purified by column chromatograph over silica using toluene/ethyl acetate as eluent to afford pure product FNIa as dark-red solid, and FNIb as orange-red solid.
  • 4
  • [ 81-86-7 ]
  • [ 68176-57-8 ]
  • C22H17BrN2O [ No CAS ]
  • C22H17BrN2O [ No CAS ]
  • C22H17BrN2O [ No CAS ]
  • C22H17BrN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid; for 5h;Reflux; A flask was charged with 4-bromo-1,8-naphthalic anhydride(2.18 g, 7.87 mmol), 4-tert-butylbenzene-1,2-diamine (1.3 g, 7.88 mmol) and acetic acid (50 mL). The mixture was heated under reflux for 5 h. After cooling to room temperature, the mixture was poured into ice water. The precipitate was filtered, washed with water and dried in vacuo. The crude product was composed of an inseparable mixture of isomers (6a-d) as a yellow solid in 76.5percentyield.
  • 5
  • [ 6398-87-4 ]
  • [ 81-86-7 ]
  • C21H14BrNO4 [ No CAS ]
  • C19H10BrNO3 [ No CAS ]
  • 6
  • [ 6398-87-4 ]
  • [ 81-86-7 ]
  • C19H10BrNO3 [ No CAS ]
  • 8
  • [ 81-86-7 ]
  • [ 29390-67-8 ]
  • C54H74BrNO36 [ No CAS ]
  • 9
  • [ 81-86-7 ]
  • [ 71176-54-0 ]
  • C20H14BrNO4 [ No CAS ]
 

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bouveault-Blanc Reduction • Bucherer-Bergs Reaction • Catalytic Hydrogenation • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Ester Cleavage • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Reactions with Organometallic Reagents • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories

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[ 81-86-7 ]

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Esters

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Related Parent Nucleus of
[ 81-86-7 ]

Other Aromatic Heterocycles

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