Chemistry Heterocyclic Building Blocks Thiophenes 2,2':5',2''-Terthiophene

2,2':5',2''-Terthiophene

Electrophilic Substitution: The electron-rich nature of the thiophene rings in 2,2':5',2''-terthiophene makes it susceptible to electrophilic substitution reactions. For example, you can react it with electrophilic reagents like nitric acid or bromine to introduce substituents onto the thiophene rings. Nucleophilic Substitution: In the presence of strong bases or nucleophilic reagents, the compound may undergo nucleophilic substitution reactions at suitable positions within the molecule. Metalation: The compound can be deprotonated at specific positions by strong bases to form metalated intermediates. These metalated intermediates can then be used in further reactions, such as cross-coupling reactions with various electrophiles. Polymerization: 2,2':5',2''-terthiophene is often used as a monomer in the synthesis of conductive polymers like polythiophenes. Polymerization reactions, such as oxidative polymerization, can convert it into conductive polymer chains. Suzuki-Miyaura Coupling: This cross-coupling reaction can be used to introduce various substituents onto the 2,2':5',2''-terthiophene molecule. It involves the reaction of the compound with aryl or vinyl boronic acids or boronate esters in the presence of a palladium catalyst. Friedel-Crafts Reactions: In some cases, Friedel-Crafts acylation or alkylation reactions can be used to introduce acyl or alkyl groups onto the thiophene rings. These reactions typically require strong Lewis acids as catalysts. Redox Reactions: 2,2':5',2''-terthiophene can participate in various redox reactions, such as electrochemical oxidation and reduction, making it useful in the development of electroactive materials.

Further Reading:

Framework+−

(9H-Fluoren-9-Yl)Methyl (2-(Thiophen-2-Yl)Ethyl)Carbamate 1-(Thiophen-2-Yl)Ethan-1-One 2,2'-Bithiophene 2,2':5',2''-Terthiophene 2,3-Dihydrothieno[3,4-B][1,4]Dioxine 2,5-Dibromothiophene 2,5-Diphenylthiophene 2-(Thiophen-2-Yl)Pyridine 2-(Trifluoromethyl)Thiophene 2-Chlorothiophene 2-Ethynylthiophene 2-Iodothiophene 2-Methoxythiophene 2-Nitrothiophene 3-Bromothiophene 3-Chlorothiophene 3-Fluorothiophene 3-Methoxythiophene 3-Methylthiophene 3-Nitrothiophene 3-Phenylthiophene 4,4,5,5-Tetramethyl-2-(Thiophen-2-Yl)-1,3,2-Dioxaborolane 4,4,5,5-Tetramethyl-2-(Thiophen-3-Yl)-1,3,2-Dioxaborolane 4,5,6,7-Tetrahydrothieno[2,3-C]Pyridine 4,5,6,7-Tetrahydrothieno[3,2-C]Pyridine 4,7-Di(Thiophen-2-Yl)Benzo[C][1,2,5]Thiadiazole 4,8-Di(Thiophen-2-Yl)Benzo[1,2-B:4,5-B']Dithiophene 4-Phenyl-6H-Thieno[3,2-F][1,2,4]Triazolo[4,3-A][1,4]Diazepine 4H-Cyclopenta[2,1-B:3,4-B']Dithiophene 4H-Thieno[3,2-B]Pyrrole 4H-Thieno[3,4-C]Pyrrole-4,6(5H)-Dione 5,6-Dihydro-4H-Cyclopenta[B]Thiophene 5-(Thiophen-2-Yl)Isoxazole 5-Benzyl-4,5,6,7-Tetrahydrothieno[3,2-C]Pyridine 5-Phenylthiophen-2-Amine Benzo[1,2-B:4,5-B']Dithiophene Dibenzo[B,D]Thiophene Dihydrothiophen-3(2H)-One Dithieno[3,2-B:2',3'-D]Thiophene Ethyl Thiophene-2-Carboxylate Ethyl Thiophene-3-Carboxylate Methyl Thiophene-3-Carboxylate N,N-Diphenyl-4-(Thiophen-2-Yl)Aniline Phenyl(Thiophen-2-Yl)Methanone Thieno[2,3-B]Pyridine Thieno[2,3-C]Pyridine Thieno[2,3-D]Pyrimidine Thieno[3,2-B]Pyridine Thieno[3,2-B]Thiophene Thieno[3,2-C]Pyridine Thieno[3,2-D]Pyrimidine Thieno[3,4-B]Thiophene Thiophen-2-Ylboronic Acid Thiophen-2-Ylmethanol Thiophen-3-Amine Thiophen-3-Ol Thiophene-2-Carbaldehyde Thiophene-2-Carbonitrile Thiophene-3-Carbaldehyde Thiophene-3-Carbonitrile Thiophene-3-Carboxamide Thiophene-3-Carboxylic Acid

By Key Group+−

Acetylthiophene Aminothiophene Bromothieno Chlorothieno Chlorothiophene Cyanothiophene Dibromothieno Dibromothiophene Dichlorothieno Dichlorothiophene Dihydrothieno Dihydrothiophene Dihydroxythiophene Dimethylthieno Dimethylthiophene Dithiophene Fluorothiophene Formylthiophene Hydroxythiophene Iodothieno Iodothiophene Methylthieno Nitrothiophene Oxotetrahydrothiophene Terthiophene Tetrahydrothieno Thiophen-Amine-Hydrochloride Thiophenecarboxaldehyde Thiphen-Amine-Hydrochloride Trithiophene

By Route Intermediates+−

cLogP+−

H-Acceptors+−

H-Donors+−

Polar Surface Area+−

Druglikeness+−

NNCH/NNH+−

sp3-Atoms+−

Non-Aromatic Rings+−

Aromatic Rings+−

Rotatable Bonds+−

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5,5''-Dibromo-2,2':5',2''-terthiophene

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[2,2':5',2''-Terthiophene]-5-carbaldehyde

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