3263-79-4

Usage

Uses

Used in Organic Electronics Industry:
2,3,4,5-Tetraphenylpyrrole is used as a semiconductor material for its good charge transport properties, making it suitable for applications in organic electronic devices such as field-effect transistors.
Used in Supramolecular Chemistry:
2,3,4,5-Tetraphenylpyrrole is used as a building block in the construction of supramolecular structures, owing to its unique molecular structure and properties.
Used in Coordination Chemistry:
2,3,4,5-Tetraphenylpyrrole is utilized as a ligand in coordination chemistry, taking advantage of its ability to form complexes with metal ions for various applications.

InChI:InChI=1/C28H21N/c1-5-13-21(14-6-1)25-26(22-15-7-2-8-16-22)28(24-19-11-4-12-20-24)29-27(25)23-17-9-3-10-18-23/h1-20,29H

Upstream product

• 10516-92-4 1,2,3,4-tetraphenylbutane-1,4-dione 
• 30506-03-7 1,2-bis(1,2-diphenylethylidene)hydrazine 
• 451-40-1 phenyl benzyl ketone 
• 631-61-8 ammonium acetate 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 302-72-7 rac-Ala-OH 
• 588-59-0 stilbene 
• 100-46-9 benzylamine 
• 5172-07-6 Desoxybenzoin-methylhydrazon 
• 1215-07-2 (E)-(1-nitroethene-1,2-diyl)dibenzene 
• 137570-31-1 3-benzoyl-1,2,3-triphenylcyclopropene imine 
• 501-65-5 diphenyl acetylene 
• 1605-06-7 cis-2,3-diphenylaziridine 
• 642-04-6 2,3,5,6-tetraphenylpyrazine 

Downstream Products

• 642-04-6 2,3,5,6-tetraphenylpyrazine 
• 2406-01-1 1-methyl-2,3,4,5-tetraphenylpyrrole 
• 103723-64-4 2-(2,4-dinitrophenylthioamino)-2,3,4,5-tetraphenyl-2H-pyrrole 
• 14277-91-9 tetraphenyl-2,4,5,6 pyrimidine 
• 4793-85-5 2,3,4,4-tetraphenyl-2-pyrrolin-5-one 
• 55-21-0 benzamide 
• 65-85-0 benzoic acid 
• 7731-75-1 α-benzoylamino-α'-benzoylstilbene 
• 7510-34-1 (Z)-1,2,3,4-tetraphenyl-2-butene-1,4-dione 
• 4793-86-6 tetraphenyl-2H-pyrrol-2-ol 
• 53309-76-5 1-ethyl-2,3,4,5-tetraphenyl-1H-pyrrole 
• 1416451-10-9 1-(dimesitylboranyl)-2,3,4,5-tetraphenyl-1H-pyrrole 
• 1420044-92-3 (tmeda)Li(Pyr^Ph₄) 
• 70148-39-9 N-Benzyl-2,3,4,5-tetraphenylpyrrole 

Relevant academic research and scientific papers

Pyrroles as antioxidants: Solvent effects and the nature of the attacking radical on antioxidant activities and mechanisms of pyrroles, dipyrrinones, and bile pigments

(Chemical Equation Presented) The absolute rate constants, kinh, and stoichiometric factors, n, of pyrroles, 2-methyl-3-ethylcarboxy-4,5-di-p- methoxyphenylpyrrole, 6, 2,3,4,5-tetraphenylpyrrole,7, and 2,3,4,5-tetra-p- methoxyphenylpyrrole, 8, compared to the phenolic antioxidant, di-tert-butylhydroxyanisole, DBHA, during inhibited oxidation of cumene initiated by AIBN at 30°C gave the relative antioxidant activities (k inh) DBHA > 8 > 7 > 6 and n = 2, whereas in styrene, 8 > DBHA. These results are explained by hydrogen atom transfer, HAT, from the N-H of pyrroles to ROO? radicals. The kinh values in styrene of dimethyl esters of the bile pigments of bilirubin ester (BRDE), of biliverdin ester (BVDE), and of a model compound (dipyrrinone, 1) gave k inh in the order pentamethylhydroxychroman (PMHC) BRDE > 1 > BVDE. These antioxidant activities for BVDE and the model compound, 1, and PMHC dropped dramatically in the presence of methanol due to hydrogen bonding at the pyrrolic N-H group. In contrast the kinh of BRDE increased in methanol. We now show that pyrrolic compounds may react by HAT, proton-coupled electron transfer, PCET, or single electron transfer, SET, depending on their structure, the nature of the solvent, and the attacking radical. Compounds BVDE and 1 react by the HAT or PCET pathway (HAT/PCET) in styrene/chlorobenzene with ROO? and with the DPPH? radical in chlorobenzene according to N-H/N-D kH/kD of 1.6, whereas the DKIE with BRDE was only 1.2 with ROO?. The antioxidant properties of polypyrroles of the BVDE class and model compounds (e.g., 1) are controlled by intramolecular H bonding which stabilizes an intermediate pyrrolic radical in HAT/PCET. According to kinetic polar solvent effects on the monopyrrole, 8, and BRDE, which gave increased rates in methanol, some pyrrolic structures are also susceptible to SET reactions. This conclusion is supported by some calculated ionization potentials. The antioxidant mechanism for BRDE with peroxyl radicals is described by the PCET reaction. Experiments using the 2,6-di-tert-butyl-4- (4′-methoxyphenyl)phenoxyl radical (DBMP?) showed this to be a better radical to monitor HAT activities in stopped-flow kinetics compared to the use of the more popular DPPH? radical.

Base-Mediated Direct Transformation of N-Propargylamines into 2,3,5-Trisubstituted 1 H-Pyrroles

An efficient and base-mediated intramolecular cyclization of N-propargylamines for the synthesis of structurally diversified pyrroles in high yield has been described. The developed methodology is broadly applicable and is tolerated by a variety of functional groups. Key intermediates of natural product discoipyrrole C as well as HMG-CoA-reductase inhibitor have been successfully synthesized using developed chemistry. The proposed mechanism was supported by control experiments.

Base-Mediated Direct Transformation of N-Propargylamines into 2,3,5-Trisubstituted 1 H-Pyrroles

An efficient and base-mediated intramolecular cyclization of N-propargylamines for the synthesis of structurally diversified pyrroles in high yield has been described. The developed methodology is broadly applicable and is tolerated by a variety of functional groups. Key intermediates of natural product discoipyrrole C as well as HMG-CoA-reductase inhibitor have been successfully synthesized using developed chemistry. The proposed mechanism was supported by control experiments.

Silver-Catalyzed Coupling of Two Csp3-H Groups and One-Pot Synthesis of Tetrasubstituted Furans, Thiophenes, and Pyrroles

Silver-catalyzed coupling of two Csp3-H groups to form 1,4-diketones have been developed for the first time. The resultant ketones then undergo cyclization to synthesize tetrasubstituted furans, thiophenes, and pyrroles from benzyl ketone derivatives in a one-pot reaction process. This highly-efficient synthetic method, which utilizes air as the terminal oxidant and readily accessible starting materials, displays a wide substrate scope and broad functional-group tolerance.

Copper-catalyzed homocoupling of ketoxime carboxylates for synthesis of symmetrical pyrroles

A novel and efficient copper-catalyzed homocoupling of ketoxime carboxylates has been developed for the synthesis of symmetrical pyrroles. This reaction tolerates a wide range of functional groups and provides a synthetically useful process to synthesize

The dual role of ruthenium and alkali base catalysts in enabling a conceptually new shortcut to N-unsubstituted pyrroles through unmasked α-amino aldehydes

A virtually salt-free and straightforward bimolecular assembly giving N-unsubstituted pyrroles through fully unmasked α-amino aldehydes, which was enabled by the dual effects of a catalytic ruthenium complex and an alkali metal base, is reported. Either solvent-free or acceptorless dehydrogenation facilitates high atom, step, and pot economy, which are otherwise difficult to achieve in multistep operations involving protection/deprotection.

Peripheral aryl-substituted pyrrole fluorophores for glassy blue-light-emitting diodes

In this work, a series of aryl-substituted pyrrole analogues were synthesized. These pyrrole analogues emit violet to blue light. Fluorescence and amorphous glassy properties of these pyrrole analogues were induced by manipulating the peripheral aryl grou

Synthesis of 2,3,4,5-tetrasubstituted pyrroles from aromatic ketoximes using the TiCl4/Et3N reagent system

Aryl alkyl ketoximes react with the TiCl4/Et3N reagent to give 2,3,4,5-tetrasubstituted pyrroles in moderate to good yields (55-81%).

Microwave mediated facile one-pot synthesis of polyarylpyrroles from but-2-ene- and but-2-yne-1,4-diones

Several pyrrole derivates with multiple aryl substituents were prepared conveniently in a one pot-reaction from but-2-ene-1,4-diones and but-2-yne-1,4-diones via hydrogenation of the carbon-carbon double bond/triple bond followed by amination-cyclization. The reaction could be performed with ammonium formate or alkyl/arylammonium formates under Pd/C in polyethylene glycol-200 (PEG-200) under microwave irradiation. Using this procedure, different aryl-substituted pyrroles were prepared. Furthermore, studies on microwave vs thermal conditions indicate faster heating under microwave conditions was responsible for rate enhancement.