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[ CAS No. 37500-95-1 ] {[proInfo.proName]}

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Chemical Structure| 37500-95-1
Chemical Structure| 37500-95-1
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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 [ 37500-95-1 ]

CAS No. :37500-95-1 MDL No. :MFCD03425849
Formula : C20H25N Boiling Point : No data available
Linear Structure Formula :((C(CH3)3)C6H3)2NH InChI Key :OYFFSPILVQLRQA-UHFFFAOYSA-N
M.W : 279.42 Pubchem ID :15469209
Synonyms :

Calculated chemistry of [ 37500-95-1 ]      Expand+

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 : 15.79 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.45
Log Po/w (XLOGP3) : 6.73
Log Po/w (WLOGP) : 5.92
Log Po/w (MLOGP) : 4.81
Log Po/w (SILICOS-IT) : 6.11
Consensus Log Po/w : 5.4

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.14
Solubility : 0.000203 mg/ml ; 0.000000727 mol/l
Class : Poorly soluble
Log S (Ali) : -6.87
Solubility : 0.000038 mg/ml ; 0.000000136 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -7.38
Solubility : 0.0000117 mg/ml ; 0.000000042 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.9

Safety of [ 37500-95-1 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

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   1~10

  • 1
  • [ 5394-23-0 ]
  • [ 37500-95-1 ]
  • [ 551951-05-4 ]
  • 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.
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