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Synthesis and characterization of new cardo poly(bisbenzothiazole)s from 1,1-bis(4-amino-3-mercaptophenyl)-4-tert-butylcyclohexane dihydrochloride

Authors

  • Wei Huang,

    1. Research Institute of Polymer Materials, School of Chemistry and Chemical Engineering, State Key Laboratory for Composite Materials, Shanghai Jiao Tong University, Shanghai 200240, People's Republic of China
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  • Hongjie Xu,

    1. Research Institute of Polymer Materials, School of Chemistry and Chemical Engineering, State Key Laboratory for Composite Materials, Shanghai Jiao Tong University, Shanghai 200240, People's Republic of China
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  • Jie Yin

    Corresponding author
    1. Research Institute of Polymer Materials, School of Chemistry and Chemical Engineering, State Key Laboratory for Composite Materials, Shanghai Jiao Tong University, Shanghai 200240, People's Republic of China
    • Research Institute of Polymer Materials, School of Chemistry and Chemical Engineering, State Key Laboratory for Composite Materials, Shanghai Jiao Tong University, Shanghai 200240, People's Republic of China
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Abstract

A new monomer 1,1-bis(4-amino-3-mercaptophenyl)-4-tert-butylcyclohexane dihydrochloride, bearing the bulky pendant 4-tert-butylcyclohexylidene group, was synthesized from 4-tert-butylcyclohexanone in three steps. Its chemical structure was characterized by 1H NMR, 13C NMR, MS, FTIR, and EA. Aromatic poly(bisbenzothiazole)s (PBTs V) were prepared from the new monomer and five aromatic dicarboxylic acids by direct polycondensation. The inherent viscosities were in the range of 0.63–2.17 dL/g. These polymers exhibited good solubility and thermal stability. Most of the prepared PBTs V were soluble in various polar solvents. Thermogravimetric analysis showed the decomposition temperatures at 10% weight loss that were in the range of 495–534°C in nitrogen. All the PBTs V, characterized by X-ray diffraction, were amorphous. The UV absorption spectra of PBTs V showed a range of λmax from 334 to 394 nm. All the PBTs V prepared had evident fluorescence emission peaks, ranging from 423 to 475 nm with different intensity. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 101: 2000–2008, 2006

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