Structure of 81-86-7
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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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 phenothiazine 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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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 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
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 |
43.37 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.87 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.23 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.91 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
3.32 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.52 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
2.97 |
Log S (ESOL):? ESOL: Topological method implemented from |
-4.06 |
Solubility | 0.0244 mg/ml ; 0.0000881 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.81 |
Solubility | 0.0425 mg/ml ; 0.000154 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-4.99 |
Solubility | 0.00282 mg/ml ; 0.0000102 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
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) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.7 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
2.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.08 |
* 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.
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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. |
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