4,4'-(9-Fluorenylidene)dianiline
FDA · BAFL · 4,4'-(9-Fluorenylidene)dianiline · BAF/FDA · FDA/BAFL · AKOS BBB/416 · Zinc03897005 · Anilinefluorene
Identifikatoren & physikalische Daten
| CAS No. | 15499-84-0 |
|---|---|
| Summenformel | C25H20N2 |
| Durchschnittliche Molmasse | 348,4 g/mol |
| Monoisotopische Masse | 348,16264864 g/mol |
| SMILES | Nc1ccc(C2(c3ccc(N)cc3)c3ccccc3-c3ccccc32)cc1 |
| InChIKey | KIFDSGGWDIVQGN-UHFFFAOYSA-N |
| PubChem CID | 631552 |
| ChEMBL | CHEMBL341910 |
| EC No. | 628-740-5 |
| DTXSID | DTXSID20348173 |
Chemische & physikalische Eigenschaften
| XLogP | 5,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 52 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 27 |
| Formalladung | 0 |
| Komplexität | 454 |
| Schmelzpunkt | 237-239 °C (lit.) |
| Siedepunkt | 535.2±50.0 °C(Predicted) |
| Dichte | 1.245±0.06 g/cm3(Predicted) |
| Lagerbedingungen | Keep in dark place,Inert atmosphere,Room temperature |
| Löslichkeit | Insoluble in water |
| Aggregatzustand | powder to crystal |
| pKa (Säurekonstante) | 4.92±0.10(Predicted) |
| Farbe | White to Almost white |
| InChI | InChI=1S/C25H20N2/c26-19-13-9-17(10-14-19)25(18-11-15-20(27)16-12-18)23-7-3-1-5-21(23)22-6-2-4-8-24(22)25/h1-16H,26-27H2 |
| InChIKey | KIFDSGGWDIVQGN-UHFFFAOYSA-N |
| SMILES | C1(C2=CC=C(N)C=C2)(C2=CC=C(N)C=C2)C2=C(C=CC=C2)C2=C1C=CC=C2 |
| CAS Datenbank | 15499-84-0(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (95.1%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance. |
| Hazard Classes and Categories | Acute Tox. 4 (95.1%) |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29215900 |
| R-Sätze (R) | 20/21/22-36/37 |
| Gefahrensymbole | Xn,Xi |
| Sicherheitshinweise (S) | 26-36 |
| Gefahrenklasse | IRRITANTAcute Tox. 4 OralEye Irrit. 2STOT SE 3 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
9,9-Bis(4-aminophenyl)fluorene (FDA) is a fluorene derivative with two aminophenyl substituents on the 9-position. This compound has partial conjugation and can be utilized as a dopant-free organic hole-transporting material in inverted perovskite solar cells. Due to its diaminophenyl groups, FDA is commonly employed in synthesizing polyimides that possess high thermal and hydrolytic stability for optical fiber light guide coatings. Because the FDA is not fully aromatized, it is chosen to produce thermally stable transparent polyimides. Additionally, the polyimide derived from 9,9-bis(4-aminophenyl)fluorene can be further modified through Friedel-Crafts alkylation on the fluorene moiety, as the polyimide backbone remains chemically stable.
Verwenden
9,9-bis(4-aminophenyl)fluorene be used for preparation of high-strength material and high-temperature polymers.
Herstellung & Synthese
synthetische
The synthesis of 9,9-Bis(4-aminophenyl)fluorene can be carried out through the following stepwise procedure:Prepare the reaction mixture:Place 3.6 g of fluorenone (20 mmol), 7.2 g of aniline hydrochloride (55.6 mmol), 0.5 g of sodium bisulfite (4.8 mmol), 8.8 mL of aniline (96.4 mmol), and 6 mL of toluene in a 100 mL two-necked flask.Ensure the reaction is conducted under nitrogen protection.Add a water separator to the two-necked flask.Begin the reaction:Stir the reaction mixture and slowly increase the temperature to 120 °C.Allow the reaction to continue for 30 minutes.Separate the green liquid produced in the water separator.Further reaction at elevated temperature:Continue the reaction at 120 °C for an additional 3 hours.Separate the water produced in the water separator.Increase temperature and maintain reaction:Slowly raise the temperature to 135 °C.Keep the reaction at this temperature for 1.5 hours.Monitor for completion:Check the water separator for any further production of water.Cease the reaction when no more water is produced in the water separator.Cool down and adjust pH:Allow the reacted material to cool to around 60 ℃.Add 10 wt% potassium hydroxide solution to the reaction mixture.Adjust the pH of the mixture to 9.Stir the solution for 15 minutes while it is still hot.Filtration and purification:Filter the solution to remove any solid impurities.Wash the filter cake with water.Recrystallize the washed filter cake using 30 mL of toluene.Filter the recrystallized product to obtain pure rice-white product.Yield determination:Weigh the obtained pure product, which should amount to 6.55 g.Calculate the yield by dividing the obtained mass by the theoretical maximum mass and multiplying by 100%.The yield of the pure rice-white product should be 94%.