89059-06-3

Usage

Uses

Used in Biosensor Applications:
1H-Pyrrole-1-propanoic acid is used as a component in multi-layered films with gold nanoparticles and nickel oxide for biosensor applications.
Used in Photoacoustic Imaging:
1H-Pyrrole-1-propanoic acid is used in photoacoustic imaging based photothermal therapy.
Used in Microsensor Applications:
1H-Pyrrole-1-propanoic acid is used as a component in electropolymerized thin films that find applications as microsensor electrode arrays.

Purification Methods

Recrystallise the acid from pet ether (b 80-100o) and dry it in vacuo. The ethyl ester has b 122o/23mm. The amide forms colourless needles from *C6H6 with m 81o and is soluble in cold H2O. [Clemo & Ramage J Chem Soc 49 1931, Jefford & Johncock Helv Chim Acta 66 2666 1983.]

InChI:InChI=1/C7H9NO2/c9-7(10)3-6-8-4-1-2-5-8/h1-2,4-5H,3,6H2,(H,9,10)

Upstream product

• 43036-06-2 3-(pyrrol-1-yl)propanenitrile 
• 50463-83-7 ethyl 3-(1-pyrrolo)propanoate 
• 99233-38-2 methyl 3-(1-pyrrolidyl)propionate 

Downstream Products

• 157614-76-1 Pentafluorophenyl 3-(pyrrol-1-yl)propanoate 
• 50966-69-3 3-pyrrol-1-yl-propan-1-ol 
• 883564-50-9 3-pyrrol-1-yl-propionic acid 2,5-bis-bromomethyl-benzyl ester 
• 157614-80-7 (3-Pyrrol-1-yl-propionylamino)-acetic acid pentafluorophenyl ester 
• 17266-64-7 1,2-dihydro-1-pyrrolizinone 
• 865763-00-4 (3-formyl-2-hydroxyphenyl) 3-(pyrrol-1-yl)propanoate 

Relevant academic research and scientific papers

The development of an ultra-sensitive electrochemical immunosensor using a PPyr-NHS functionalized disposable ITO sheet for the detection of interleukin 6 in real human serums

A label-free impedimetric immunosensor based on a conjugated poly(pyrrole N-hydroxy succinimide) (PPyr-NHS) polymer covered disposable indium tin oxide electrode (ITO) was fabricated for the ultrasensitive determination of interleukin 6 (IL 6) antigen. In this sensing platform, the PPyr-NHS polymer, which carried a number of succinimide groups on its end side, was used as a matrix material for the first time. This synthesized polymer had excellent biocompatibility and good electrical conductivity. In addition, the utilization of this material as a matrix material provided direct immobilization of the IL 6 receptor (IL6R), which was employed as a biorecognition element. The preparation of the working electrode, the successful attachment of IL 6R and specific interaction between IL6R and IL 6 antigen were confirmed by electrochemical impedance spectroscopy (EIS) and cyclic voltammetry (CV) techniques. Moreover, the working electrode surface was characterized by Scanning electron microscopy (SEM), Atomic force microscopy (AFM), Fourier transform infrared spectroscopy (FTIR) and Raman spectroscopy during its construction. An impedimetric method was employed for the quantification of IL 6 antigen. Under optimized experimental conditions, the designed sensing platform could detect IL 6 antigen with a wide detection range from 0.03 pg mL-1 to 22.5 pg mL-1 with a relatively low detection limit of 10.2 fg mL-1. In addition, the developed biosensor had outstanding sensitivity and specificity, good repeatability and reproducibility, high stability and reusability. Additionally, the designed sensing tool was successfully used in human serum samples. Consequently, the suggested immunosensor was clinically useful in the early detection of prostate cancer by direct determination of the serum IL 6 antigen level after simple dilution.

A hydrazide organogelator for fluoride sensing with hyperchromicity and gel-to-sol transition

Sensing of fluoride in a solvent is highly required in healthcare and environmental rehabilitation. Among the various sensing methods, optical sensing has attracted significant research interest because it can conveniently recognize fluoride. Herein, a low molecular weight organogelator, N′1,N′6-bis(3-(1-pyrrolyl)propanoyl) hexanedihydrazide (DPH), containing a central butyl chain conjugated to two pyrrole rings through hydrazide groups, was used for optical sensing of fluoride in the forms of both solution and organogel. Association of fluoride with the -NH moiety of the hydrazide group endowed the DPH solution in dimethylformamide with a hyperchromicity under 350 nm. Exploiting the UV absorptivity, the DPH solution was examined as a chemosensor, displaying good selectivity toward fluoride among various anions and moderate sensitivity with a detection limit of 0.49 μM. The practical use of the DPH solution was demonstrated for fluoride sensing in toothpaste. Binding of fluoride also changed the molecular interactions of the DPH organogel, resulting in a phase transition from gel to sol. This gel-to-sol transition enabled the sensing of fluoride by the naked eye.

Electrochemical polymerization of pyrrole containing TEMPO side chain on pt electrode and its electrochemical activity

Poly(4-(3-(pyrrol-1-yl)propionyloxy)-2,2,6,6-tetramethylpiperidin-1-yloxy) (PPy-TEMPO) electrode is prepared by electrochemical polymerization on Pt electrode in NaClO4-CH3CN solution. The electrocatalytic activity of PPy-TEMPO for benzyl alcohol in NaClO4-CH3CN solution is investigated by cyclic voltammetry and in situ FTIR. Results show that PPy-TEMPO electrode exhibits high electrocatalytic activity for benzyl alcohol oxidation in the presence of 2,6-lutidine as the base, as compared with the bare Pt electrode under the similar conditions. On the basis of in situ FTIR data, it shows that TEMPO is oxidized to its cation at the potential about 0.4 V, and benzyl alcohol is oxidized to benzaldehyde instead of benzoic acid. Further studies of preparative electrolysis experiments by constant current electrolysis are carried out to confirm the high conversion to benzaldehyde, and the results are in good agreement with those from in situ FTIR investigations.

Conductive microrod preparation by molecular self-assembly and polymerization

Conductive microrods were prepared by evaporation-induced self-assembly (EISA) and subsequent polymerization of a novel, self-assembling molecule with pyrrole end groups. The newly synthesized self-assembling molecule of N′1,N′6-bis(3-(1-pyrrolyl)propanoyl) hexanedihydrazide self-assembled from a dilute solution into microrods. Pyrrole ring stacking was the key driving force inducing molecular self-organization to microrods. After the self-assembly, the pyrrole groups on the surface of the microrods were chemically polymerized to make the microrod conductive. The electrical conductance of the polymerized microrods was comparable to that of other conducting polymer microrods. Analyses of the polymerized microrods confirmed that the polymerization took place only at the surface of the microrod assembly. This study proved the concept of self-assembly and polymerization to generate complex structured functional materials, and is valuable for the design of functional self-assembling molecules.

Electropolymerizable monomers and polymeric coatings on implantable devices prepared therefrom

Conductive surfaces of e.g., implantable devices, coated with electropolymerized polymers having active substances attached thereto are disclosed. Electropolymerizable monomers designed and used for obtaining such conductive surfaces and processes, devices and methods for attaching the electropolymerized polymers to conductive surfaces are also disclosed. The polymers, processes and devices presented herein can be beneficially used in the preparation of implantable medical devices.

Sensitive amperometric immunosensing using polypyrrolepropylic acid films for biomolecule immobilization

An electrochemical immunosensor was constructed using an electropolymerized pyrrolepropylic acid (PPA) film with high porosity and hydrophilicity. A high density of carboxyl groups of PPA was used to covalently attach protein probes, leading to significantly improved detection sensitivity compared with conventional entrapment methods. As a model, anti-mouse IgG was covalently immobilized or entrapped in the PPA film and used in a sandwich-type alkaline phosphatase-catatyzing amperometric immunoassay with p-aminophenyl phosphate as the substrate. With covalent binding, the detection limit for IgG in PBS buffer, pH 7.4, was 100 pg/mL with a dynamic range of 5 orders of magnitude. The covalent bonding mode in the carbonate-bicarbonate buffer, pH 9.6, further brought down the detection limit to 20 pg/mL with remarkable selectivity.

Synthesis and characterization of salen-type ligands functionalized with pyrrole derivative pendant arms

Several salen-type ligands functionalized with two pyrrole derivative pendant arms were prepared. These Schiff base ligands, which differ in the imine bridge, were prepared by a multi-step procedure that includes (i) synthesis of 3-pyrrol-1-ylpropanoic acid, (ii) transformation of the latter compound into the mixed carboxylic-carbonic anhydride (MCCA) intermediate followed by reaction with 2,3-dihydroxybenzaldehyde to give (3-formyl-2-hydroxyphenyl) 3-(pyrrol-1-yl)propanoate and finally (iii) Schiff condensation of the different 1,2-diamines with (3-formyl-2-hydroxyphenyl) 3-(pyrrol-1-yl)propanoate. The key step in the Schiff base ligand preparation is the functionalization of the 2,3-dihydroxybenzaldehyde at the C-3 hydroxyl group without protection of the C-2 hydroxyl group, by a regiospecific acylation of the ortho-hydroxyl group via esterification with the mixed carboxylic-carbonic anhydride of 3-pyrrol-1-ylpropanoic acid. The compounds were characterized by elemental analyses, 1H and 13C NMR spectroscopy, mass spectrometry and FTIR and UV-visible spectrophotometry. Copyright

Polypyrrole-supported graphite felt for acetylene coupling reaction in solid phase

Substrate immobilization on graphite felt for solid-phase acetylene coupling reaction was achieved by electrochemical polymerization of the substrate precursor containing a pyrrole side chain, where the amount of substrate on the electrode surface was easily controlled by the number of repeated cyclic voltammetric scannings. Couplings between terminal acetylenes and the iodobenzene-modified graphite felt electrode or aromatic iodides and the terminal acetylene-modified graphite felt electrode in the presence of palladium catalyst proceeded smoothly in satisfactory yields.

Acyl radical cyclisation onto pyrroles

Synthetically useful [1,2-a]-fused pyrroles, e.g. 2,3-dihydro-1H-pyrrolizidines substituted in the 1- and 7-positions, have been generated by acyl radical cyclisation onto pyrroles using N-(ω-acyl)-radicals generated from acyl-selenide precursors. The protocol does not require high pressures of CO. Mechanistic studies indicate the key role of azo radical initiators as oxidants of the intermediate π-radicals.

Functionalization of polypyrroles with acids and β-diketones as complexing groups. Part 1: Electrochemical synthesis and properties

The synthesis of pyrroles functionalized by complexing groups such as acetylacetone, dibenzoylmethane or carboxylic acids is described, as well as their electrooxidation into functionalized polypyrroles. We have studied the behavior of poly(functionalized pyrrole) films in the presence of Li+, Ni2+ and Co2+ cations by cyclic voltammetry (CV) and infrared (IR) spectroscopy. The electrochemical response under various conditions differs with the nature of the complexing group. We have also demonstrated the possibility to electrochemically generate copolymers with pyrrole and each functionalized pyrrole. The proportion of functional groups in the copolymers was estimated by following the peak potential dependence in cyclic voltammetry and was confirmed by IR spectroscopy.