Synthesis and selective recognition toward zinc ion of chiral poly(imine-triazole)

• Published in: Journal of polymer science. Part A, Polymer chemistry Vol. 52; no. 16; pp. 2248 - 2257
• Main Authors: Zhou, Jinting, Lu, Wei, Hu, Fangyu, Zhang, Mengyu, Jiang, Liming, Shen, Zhiquan
• Format: Journal Article
• Language: English
• Published: Hoboken, NJ Blackwell Publishing Ltd 15.08.2014; Wiley; Wiley Subscription Services, Inc
• Subjects: Applied sciences; chiral; click reaction; Complexation; Dichroism; Exact sciences and technology; Fluorescence; Fourier transforms; Infrared spectroscopy; Monomers; Organic polymers; Physicochemistry of polymers; Polymerization; Polymers with particular properties; polytriazole; Preparation, kinetics, thermodynamics, mechanism and catalysts; sensors; Spectra; zinc ion; 1,3-Dipolar cycloaddition; Circular dichroism spectrum; Optically active polymer; Propargylic compound; Fluorescence; Metal ion; Schiff base polymer; Chiral compound; polytriazole; Optical properties; Fluorescence detector; chiral; Organic azide; click reaction; Cyclopolymerization; Experimental study; Functional polymer; Organic solution; Cyclopolymer; Ionic selectivity; Triazole derivative polymer; sensors; Medium effect; Preparation; Optical activity; Phenols; Zinc ion
• DOI: 10.1002/pola.27223
• ISSN: 0887-624X

ABSTRACT A novel AB type of clickable monomer, (S)‐2‐[(2‐azido‐1‐phenylethylimino)methyl]‐5‐propargyloxyphenol (AMPP) was designed and polymerized to yield a class of main‐chain chiral poly(imine‐triazole)s through the metal‐free click reaction. With the thermally induced polymerization, the desired polytriazoles can be easily prepared in high yields by a stepwise heating‐up process and have the number‐average molecular masses ranging from 5.1 × 103 to 58.1 × 103 (polydispersity indices = 1.38−1.68). The polymers were characterized by Fourier Transform Infrared spectroscopy (FTIR), 1H Nuclear Magnetic Resonance (NMR), and gel permeation chromatography, and their optical properties were studied by fluorescence and circular dichroism (CD) spectroscopies. As a chemosensor, these polymers exhibited a selective “turn‐on” fluorescence enhancement response toward Zn2+ ion over other cations such as Na+, K+, Mg2+, Ca2+, Ag+, Pb2+, Cd2+, Hg2+, Mn2+, and Ni2+ in dimethyl sulfoxide. However, the Zn2+‐induced fluorescence signal was subject to serious interference by Al3+, Cu2+, Cr3+, and Fe3+ ions. Interestingly, the chiral polymer showed distinctive changes in the CD spectra on complexation with Zn2+, which allowed for the discrimination of this ion in the presence of other species tested including those interfering ions observed in the fluorescent detection. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 2248–2257 A clickable monomer (S)‐2‐[(2‐azido‐1‐phenylethylimino)methyl]‐5‐propargyloxyphenol was created and used to synthesize the corresponding polytriazoles by the thermally induced polyaddition. These chiral polymers not only exhibited highly selective “turn‐on” fluorescence response toward Zn2+ over other cations, but also produced distinctive changes in the CD spectra on complexation with Zn2+. This allowed for the discrimination of this ion in the presence of other species tested, including those interfering ions observed in the fluorescent detection.