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Synthesis and Enhanced Photofluorescence of Pyrazoline‐Ester Copolymers from Bisdiazoacetates and Diacrylates
Author(s) -
Cao Ting,
Chen Cheng,
Liu Li Jian
Publication year - 2018
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201800023
Subject(s) - copolymer , pyrazoline , polymer chemistry , chemistry , polymer science , organic chemistry , polymer
Abstract Photofluorescent pyrazoline‐ester copolymer is synthesized from bisdiazoacetate and diacrylate through two tandem 1,3‐dipolar cycloadditions at room temperature. The first 1,3‐dipolar cycloaddition takes place between bisdiazoacetate and diacrylate, and produces the diazoacetate and acrylate‐terminated pyrazoline monomer that undergoes second 1,3‐dipolar cycloaddition further to form pyrazoline‐ester copolymer in excellent yield (up to 90%) with number‐average molecular weights ( M n ) in the range of 6100–17900 g mol −1 . The optimized bisdiazo and dialkene are 1,4‐cyclohexanedimethyl bisdiazoacetate and 1,6‐hexanediol diacrylate, from which the pyrazoline‐ester copolymer with M n 17900 g mol −1 is obtained in 97% yield and the maximum emission intensity ( I / N ) is enhanced to be as high as 19 × 10 4 a.u.. The pyrazoline‐ester copolymers are down/upconversion fluorescence materials, which emit 320–330 nm UV light through the excitation of both mid‐UV and visible light, and could find wide application in the optical field.