4,4″-bis(trifluoromethyl)-[1,1':4′,1″-terphenyl]-2′,5′-dicarbaldehyde

Base Information

• Chemical Name: 4,4″-bis(trifluoromethyl)-[1,1':4′,1″-terphenyl]-2′,5′-dicarbaldehyde
• CAS No.: 1300701-03-4
• Molecular Formula: C₂₂H₁₂F₆O₂
• Molecular Weight: 422.326

Synonyms:4,4″-bis(trifluoromethyl)-[1,1':4′,1″-terphenyl]-2′,5′-dicarbaldehyde

Chemical Property of 4,4″-bis(trifluoromethyl)-[1,1':4′,1″-terphenyl]-2′,5′-dicarbaldehyde

Chemical Property:

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Technology Process of 4,4″-bis(trifluoromethyl)-[1,1':4′,1″-terphenyl]-2′,5′-dicarbaldehyde

There total 1 articles about 4,4″-bis(trifluoromethyl)-[1,1':4′,1″-terphenyl]-2′,5′-dicarbaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

2,5-dibromoterephthalaldehyde (63525-48-4) + 4-trifluoromethylphenylboronic acid (128796-39-4) → 4,4″-bis(trifluoromethyl)-[1,1':4′,1″-terphenyl]-2′,5′-dicarbaldehyde (1300701-03-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In water; toluene; at 80 ℃; for 48h; Inert atmosphere;

DOI:10.1016/j.dyepig.2019.107689

Reference yield: 87.0%

4,4″-bis(trifluoromethyl)-[1,1':4′,1″-terphenyl]-2′,5′-dicarbaldehyde (1300701-03-4) + 1-(cyanomethyl)-4-(diphenylamino)benzene → (2Z,2′Z)-3,3'-(4,4″-bis(trifluoromethyl)-[1,1':4′,1″-terphenyl]-2′,5′-diyl)bis(2-(4-(diphenylamino)phenyl)acrylonitrile)

Guidance literature:

With sodium methylate; In ethanol; for 6h; Inert atmosphere; Reflux;

DOI:10.1016/j.dyepig.2019.107689

Reference yield: 81.0%

4,4″-bis(trifluoromethyl)-[1,1':4′,1″-terphenyl]-2′,5′-dicarbaldehyde (1300701-03-4) + 1,3,5-trimethyl-benzene (108-67-8) → C40H32F6 (1621433-71-3)

Guidance literature:

With trifluorormethanesulfonic acid; acetic anhydride; In 1,2-dichloro-ethane; at 20 ℃; Green chemistry;

DOI:10.1039/c4ra03126a

upstream raw materials:

2,5-dibromoterephthalaldehyde

4-trifluoromethylphenylboronic acid

Downstream raw materials:

2-(3-(4-(4-(dimethylamino)styryl)-2,5-(4',4''-di(trifluoromethyl)phenyl)styryl)-5,5-dimethylcyclohex-2-enylidene)malononitrile

2-(3-cyano-(4-(4-(dimethylamino)styryl)-2,5-(4',4''-di(trifluoromethyl)phenyl)styryl)-5,5-dimethylfuran-2(5H)-ylidene)malononitrile

C₄₀H₃₂F₆

Refernces

Reversible solid-state mechanochromic luminescence originated from aggregation-induced enhanced emission-active Donor?Acceptor cruciform luminophores containing triphenylamine

10.1016/j.dyepig.2019.107689

This study investigates the design, synthesis, and properties of two torsional donor-acceptor cross-shaped luminophores, FB-CTPAEB and DFB-CTPAEB. These compounds exhibit unique intramolecular charge transfer (ICT) and solid-state fluorescence behaviors, and have high solid-state luminescence efficiencies (up to 0.693 and 0.442, respectively). 4,4''-Bis(trifluoromethyl)-[1,1':4',1''-terphenyl]-2',5'-dicarboxaldehyde (3a), prepared from 2,5-dibromoterephthalaldehyde and aromatic boronic acid 2a via Suzuki-Miyaura coupling reaction, is an intermediate for the synthesis of FB-CTPAEB. 3,3'',5,5''-Tetrakis(trifluoromethyl)-[1,1':4',1''-terphenyl]-2',5'-dicarboxaldehyde (3b), prepared from 2,5-dibromoterephthalaldehyde and aromatic boronic acid 2b via Suzuki-Miyaura coupling, is an intermediate compound used in the synthesis of DFB-CTPAEB. 2-(4-(Diphenylamino)phenyl)acetonitrile is used as the donor moiety in the Knoevenagel condensation reaction to form the final cruciform luminophore. 2,5-Dibromoterephthalaldehyde is the starting material for the synthesis of cruciform luminophores.

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