Structure of 113893-08-6
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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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Górski, Krzysztof ; Pejov, Ljupcho ; Jørgensen, Kåre B ; Knysh, Iryna ; Jacquemin, Denis ; Gryko, Daniel T
Abstract: Here we present a highly versatile synthetic strategy based on twofold 6π-electrocyclization accompanied with HBr elimination as a novel approach towards centrosymmetric multi-heteroatom-doped nanographenes build around an electron-rich 1,4-dihydropyrrolo[3,2-b]pyrrole core. A straightforward synthesis from readily available substrates offers a unique possibility of fusing the 1,4-dihydropyrrolo[3,2-b]pyrrole subunit not only with carbocyclic building blocks, such as electron-deficient phenanthrenes, chrysenes, or [4]helicenes, but also with heterocyclic systems, such asbenzo[b]furan and 5-thiatruxene. The clear advantage of this strategy is that there is no requirement to assemble complex scaffolds possessing bromoaryl units since bromine atom is introduced by bromination of 1,4-dihydropyrrolo[3,2-b]pyrrole core which, because of its exceptionally electron-rich character, is straightforward reaction. The obtained χ-shaped and S-shaped nanographenes containing 10or more fused rings, exhibit visible-range emissions characterized by fluorescence quantum yields reaching 48%. Computational studies of the reaction mechanism revealed that the 6π-electrocyclization is kinetically favourable over photo-induced direct arylation. Steadystate UV/Visible spectroscopy reveals that upon photoexcitation, the prepared S-shaped N-doped nanographenes undergo mostly radiative relaxation leading to large fluorescence quantum yields. We anticipate that this chemistry will empower the creation of new materials with various functionalities.
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Keywords: Dyes/Pigments ; Photochemistry ; Nanographenes ; Pyrrole ; Fluorescence
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CAS No. : | 113893-08-6 |
Formula : | C8H7BO2S |
M.W : | 178.02 |
SMILES Code : | OB(O)C1=CSC2=C1C=CC=C2 |
MDL No. : | MFCD01114669 |
InChI Key : | QVANIYYVZZLQJP-UHFFFAOYSA-N |
Pubchem ID : | 2776344 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 9 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 2.0 |
Molar Refractivity | 51.65 |
TPSA ? Topological Polar Surface Area: Calculated from |
68.7 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.0 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.84 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.58 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.64 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.02 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.82 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.59 |
Solubility | 0.456 mg/ml ; 0.00256 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-2.9 |
Solubility | 0.222 mg/ml ; 0.00125 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.23 |
Solubility | 1.05 mg/ml ; 0.00587 mol/l |
Class? Solubility class: Log S scale |
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 |
No |
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) |
No |
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 |
-6.08 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 |
1.0 |
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 |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.25 |
* 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 |
---|---|---|
73% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 155℃; for 0.333333h;Microwave irradiation; | General procedure: To a mixture of compound 7a (1 mmol), the corresponding (het)arylboronic acid 11 (1.2 mmol), Pd(PPh3)4 (58 mg, 0.05 mmol) in degassed THF (3 mL), a solution of K2CO3 (346 mg, 2.5 mL) in water (4 mL) were added. The reaction mixture was microwave irradiated at 155 C (250 W) for 20 min, then solvent was removed in vacuo. Products were isolated by column chromatography (elution with ethyl acetate-hexane, 1 : 2). |
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