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[ CAS No. 81-86-7 ] {[proInfo.proName]}

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Chemical Structure| 81-86-7
Chemical Structure| 81-86-7
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Product Citations

Product Citations

Grzelak, Magdalena ; Kumar, Dharmendra ; Kochman, Micha? Andrzej , et al. DOI: PubMed ID:

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 MDL No. :MFCD00006927
Formula : C12H5BrO3 Boiling Point : -
Linear Structure Formula :BrC10H5(CO)2O InChI Key :DTUOTSLAFJCQHN-UHFFFAOYSA-N
M.W : 277.07 Pubchem ID :66493
Synonyms :

Calculated chemistry of [ 81-86-7 ]      Expand+

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 : 43.37 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.7 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.87
Log Po/w (XLOGP3) : 3.23
Log Po/w (WLOGP) : 2.91
Log Po/w (MLOGP) : 3.32
Log Po/w (SILICOS-IT) : 3.52
Consensus Log Po/w : 2.97

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.06
Solubility : 0.0244 mg/ml ; 0.0000881 mol/l
Class : Moderately soluble
Log S (Ali) : -3.81
Solubility : 0.0425 mg/ml ; 0.000154 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.99
Solubility : 0.00282 mg/ml ; 0.0000102 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.08

Safety of [ 81-86-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

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 ]
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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
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