Synthesis and characterization of new optically active poly(acrylamide/methacrylurea-co-vinyl acetate) copolymers with dansyl units

Abstract

Novel optically active copolyacrylates synthesized by conventional radical polymerization of R/S-(+/−)-α-ethylbenzylacrylamide (R/S-EBzA) or R/S-(+/−)N-methacryloyloxyehtyl-N′-α-ethylbenzyl(urea) (R/S-MEBzU) and the vinyl acetate (VAc) in the presence of 1,1′-azobis (cyclohexanecarbonitrile) as the initiator showed optical rotation values ([α] D 23 ) of +45°/−50°for R/S-EBzA-co-VAc and of −40°in the case of S-MEBzU-co-VAc. Next, the hydrolysis reaction of the synthesized copolymers was accompanied of their chemical modification with dansyl chloride in order to obtain novel photopolymers. The structure, some physical and chemical properties of these polymers were investigated through spectral and thermal analysis ( 1 H-NMR, FTIR, UV/vis and fluorescence, and DSC), gel permeation chromatography, and optical measurements. The sensing capacity of the above photopolymers was examined by fluorescence spectroscopy in parallel with quenching studies using various acids (1-S-camphorsulfonic acid, p-toluenesulfonic acid, HCl) and metal ions (Cu 2+ , Hg 2+ , Fe 2+ ). The results revealed that the dansyl fluorophore could be useful in sensor applications for detection of some metal ions and in monitoring the protons in organic medium, the most efficient quencher being Fe 2+ and HCl for all dansyl-labeled polyacrylates.

Pyrene functionalized side chain alanine and histidine containing copolyacrylates prepared by free radical copolymerization

“…In view of our previous studies related of the photophysical aspects of some macromolecular fluorophores in the field of chemical sensors which reflected some changes in their microenvironment such as polarity, fluidity, order, molecular mobility, pH, or electric potential, we have investigated further the absorption and emission behavior of a pyrene‐substituted chiroptical copolyacrylate by adding of various nitroaromatics (picric acid, nitrobenzene, o ‐nitrophenol, p ‐nitrotoluene) in polar medium, using UV/vis and fluorescence quenching studies. The absorption spectrum of poly(Ac‐ L ‐Ala‐ co ‐Ac‐ L ‐His)‐Py in DMF solution (Figure ) showed four absorption bands located at 278, 314, 328, and 345 assigned to the pyrene‐rings.…”

“…In previous articles, our group reported data concerning a series of new fluorescent and optically active poly(meth)acrylates with side chains containing amino acids moieties, such as phenylalanine, serine, leucine, etc., along with the study of different fluorescent units, namely fluorescein‐isothiocyanate, pyrene, stilbene, and so on . In this context, the objective of the present work is focused on the study of a side chain alanine and histidine containing copolyacrylate synthesized through conventional free radical polymerization, for which N ‐acryloyl‐ L‐ alanine and N ‐acryloyl‐ L‐ histidine have been chosen as monomers.…”

NITROAROMATIC COMPOUND SENSING APPLICATION OF HEXA-ARMED DANSYL END-CAPPED POLY(epsilon-CAPROLACTONE) STAR POLYMER WITH PHOSPHAZENE CORE

“…Dimethylamino moiety works as the electron donor while sulfonic acid group acts as the acceptor. Because of these characteristics, dansyl fluorophore was widely used as fluorescent probe for the detection of various materials [18][19][20][21][22] or as a label for bio-imaging [36,37]. …”

“…Murariu et al prepared optically active dansyllabeled copolyacrylates for sensitive and selective detection of transition metal ions. They showed that the dansyl side-functional copolymers selectively responded the presence of Fe 2+ cations [22]. Dansyl-containing polymers were mainly used for the fluorescent detection of ionic species.…”

Synthesis, Characterization, and Chemosensing Application of Poly(methyl Methacrylate-Co-Hydroxyethyl Methacrylate) With Dansyl Side Group

“…Yin et al produced thermoresponsive microgels, based on dansyl-containing poly(N-isopropylacrylamide) (PNIPAM), for the selective fluorescent detection of Cu 2+ cations [29]. Murariu and Buruiana prepared dansyl-labelled poly(acrylamide/methacrylurea-co-vinyl acetate) copolymers for the fluorescent sensing studies towards some organic acids (1-S-camphorsulfonic acid and p-toluenesulfonic acid) and cations (H + , Cu 2+ , Hg 2+ , and Fe 2+ ) [30]. Recently, we have synthesized dansyl end-functional phosphazene-cored poly(ε-caprolactone) star polymer and employed as a selective fluorescent probe for the detection of Pb 2+ [1].…”