4934-25-2

Upstream product

• 586-95-8 pyridine-4-methanol 
• 103-80-0 phenylacetyl chloride 
• 872-85-5 pyridine-4-carbaldehyde 

Downstream Products

• 103-82-2 phenylacetic acid 
• 2301-80-6 N-methyl-4-methylpyridinium iodide 

Relevant academic research and scientific papers

Carbon dots as photocatalysts for organic synthesis: Metal-free methylene-oxygen-bond photocleavage

We report for the first time that irradiation of four different citric acid-derived carbon dots (CDs), in the absence of any other redox mediators, promotes an organic reaction. In this proof-of-concept study methylene-oxygen bond reductive photocleavage in N-methyl-4-picolinium esters is demonstrated. Cyclic voltammetry and UV-Vis spectra of the CDs and of the esters indicate that photocleavage reactivity correlates with the redox properties and the relative energies expressed in the Fermi scale. A photo-fragmentation mechanism is proposed. This study offers a new possibility to employ inexpensive and readily available CDs to promote photo-organic reactions.

Photoinduced Electron Transfer (PET)-Mediated Fragmentation of Picolinium-Derived Redox Probes

The photolysis of covalently linked N-alkyl picolinium phenylacetate—carbazole dyads was analyzed experimentally and by using density functional theory (DFT) and time dependent-DFT (TD-DFT) calculations. In contrast to earlier observations efficient one and two-photon fragmentations conditions were found for 15 c (δu=0.16 GM at 730 nm) opening the way for the design of a novel class of “caged” compounds.

Visible Light Photorelease of Carboxylic Acids via Charge-Transfer Excitation of N-Methylpyridinium Iodide Esters

Iodide contrast sensitization to direct irradiation of charge transfer salts incurs carboxylic acid release via visible light absorption. The photochemical reduction of N-methyl-4-pyridinium iodide esters to release carboxylic acids is examined using 1H NMR analysis. Photolysis reactions are carried out under mild, biphasic solvent conditions using a household LED lamp. Carboxylic acid release is reported in high yields, and the viability of this method for synthetic chemistry is demonstrated through a macroscale reaction.

New two- and three-cationic polymethine dyes. Synthesis, properties and application

Three new two- and three-cationic monochromophoric polymethine dyes based on the 2-methylbenzothiazole were synthesized and applied as visible light initiators for acrylic monomer polymerization. In the photoinitiating system, the polymethine dye cation a

Photorelease of carboxylic acids, amino acids, and phosphates from N-alkylpicolinium esters using photosensitization by high wavelength laser dyes

Visible light (>450 nm) is used to efficiently cleave carboxylic acids, amino acids, and phosphates from their N-methyl picolinium esters. Photolysis using pyrromethene dyes PM 546 and PM 597 and also coumarin 6 as photosensitizers effects release of carboxylic acids, N-protected amino acids, and phosphates in quantitative yields. The effective rate of photorelease by the dyes, Φε, was found to be as high as 4500 M-1 cm-1. The photorelease proceeds through photoinduced electron transfer from the dye sensitizers to the N-methyl picolinium group. Fluorescence quenching and laser flash photolysis experiments support the photoinduced electron-transfer mechanism. Copyright

C-O bond fragmentation of 4-picolyl- and N-methyl-4-picolinium esters triggered by photochemical electron transfer

Photochemical reduction of several 4-picolyl- and N-methyl-4-picolinium esters was examined using product analysis, laser flash photolysis, and fluorescence quenching. It is demonstrated that the radical (anions) formed in these reactions readily fragment to yield a carboxylic acid and a 4-pyridylmethyl radical intermediate. The high chemical and quantum yields observed for these photoreactions suggests that these esters can be used as photolabile protecting groups.