Synthesis and Characterization of New Acrylate and Methacrylate Monomers with Pendant Pyridine Groups

Abstract

To overcome some drawbacks of polyvinylpyridines, new monomers of acrylate and methacrylate type with pendant pyridine groups i.e., 4‐(3‐methacryloylpropyl)pyridine 1a and 4‐(3‐acryloylpropyl)pyridine 1b were successfully prepared, although it turned out to be challenging work to synthesize the acrylate monomer 1b. First polymerization studies showed that the new monomers could be polymerized easily by atom transfer radical polymerization (ATRP). The new polymers show excellent characteristics, such as very good solubility, low glass‐transition temperature, and easy quaternization. Design and structure of new monomers 1a and 1b.magnified imageDesign and structure of new monomers 1a and 1b.

The Thermophilic CotA Laccase from Bacillus subtilis: Bioelectrocatalytic Evaluation of O2 Reduction in the Direct and Mediated Electron Transfer Regime

“…4 and Na 2 SO 4 were purchased from Riedel-de-Haen. Osmium-bis-N,N-(2,2'-bipyridil)-dichloride, 2-(2-pyridin-2-yl-1H-imidazol-1-yl)ethyl acrylate and 4-pyridyl-propyl methacrylate were synthesized following previously described procedures [29][30][31]. Syntheses of Os-complex modified polymers were carried out by a free-radical polymerization followed by a ligand-exchange reaction between Osmium-bis-(2,2'-bipyridil)-dichloride and functional groups of the copolymer similar to [32,33].…”

Syntheses and Characterization of Luminescent Polymers Containing Rhenium(I) Pyridinyl‐Carbonyl Complexes

“…Polymerization of 4 was observed to be inefficient, yielding only tetramers and pentamers 9 with number-average molecular weights, M n < 1 300 g Á mol À1 , most probably because of an intrinsic low polymerization efficiency of the a-methylstyrene groups. [26,27] As expected, the presence of two methylene spacers in monomer 6 allowed for the formation of homopolymer 10 with M n of 3 000 g Á mol À1 . In the case of copolymers 11 and 12, M n values of 119 000 and 6 500 g Á mol À1 were obtained thanks to the presence of the butyl acrylate monomers.…”

“…All these molecular units show good photostability in the UV region, low optical density in the 320-450 nm spectroscopic region, dominated by the MLCT bands of the Re chromophore, and high polymerization and copolymerization efficiencies under thermally initiated free-radical polyaddition reactions. [26,27] Scheme 1 shows the synthetic approach developed for the preparation of two types of monomeric systems. The 2-hydroxyethyl methacrylate was reacted with isonicotinoyl acyl chloride 5 to give the monomer 6 which can be directly used as the entering ligand in the reaction with [fac-Re(CO) 3 (phen)(acetone)] þ (7) to form the new polymerizable metal-containing unit 8.…”

“…The main advantage in the use of monomer 6 lies in the existence of the two methylene spacers between the polymerizable acrylate group and the coordinated pyridine moiety, which allow for a high polymerization efficiency even in the presence of sterically hindered side groups. [26,27] The a-methylstyrene derivative containing the pyridine units, monomer 4, was obtained by reacting the isocyanate group with 4-hydroxymethylenepyridine 3, generated by chemical reduction of the isonicotinic ethyl ester 2.…”

Synthesis and Characterization of Supramolecular Polymeric Materials Containing Azopyridine Units

“…It has been reported that the interaction of pyridine side groups of polymers with polystyrene gel in GPC columns may result in lower values than the actual ones. [17] Therefore, an attempt to study the true molecular weight and macromolecular distribution of these polymers was carried out by MALDI-TOF mass spectroscopy. The resulting mass spectra of the polymers were indicative of a very low polydisperse distribution for all polymers (around 1.01), which is unlikely for a free radical polymerization (see Figure 6 as an example).…”