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Colorless polyimides derived from 2R, 5R, 7S, 10S-naphthanetetracarboxylic dianhydride

Abstract

A novel alicyclic dianhydride, 2R,5R,7S,10S-naphthanetetracarboxylic dianhydride (HNTDA), was prepared through the hydrogenation of tetramethyl 1,4,5,8-naphthalenetetracarboxylate, followed by deprotection and dehydration reactions. Single crystal X-ray diffraction results revealed that HNTDA possessed an irregular L-shaped architecture with one anhydride ring equatorial, and the other axial on the naphthane ring. Conventional one-step solution polycondensation of HNTDA with commercial diamines enabled the preparation of fully or semi-alicyclic polyimides with sufficient molecular weights. The properties HNTDA-based polyimides were systematically characterized and compared with their counterparts based on 1S,2R,4S,5R-cyclohexanetetracarboxylic dianhydride (HPMDA). Dynamic mechanical thermal analysis, thermogravimetric analysis, thermal mechanical analysis, and tensile testing indicated that HNTDA-based polymers exhibited markedly higher thermal and mechanical properties compared with HPMDA-based ones. These improvements can be rationalized according to the rigid, bulky, fused naphthanetetracarboxydiimide moiety, and the pronounced inter- and intra-molecular interactions. Furthermore, HNTDA-based polyimides were colorless or pale-yellow, and displayed good optical transparency, although their cutoff wavelength values were higher than those of HPMDA-based ones.

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Publication details

The article was received on 22 Jun 2017, accepted on 13 Sep 2017 and first published on 13 Sep 2017


Article type: Paper
DOI: 10.1039/C7PY01048F
Citation: Polym. Chem., 2017, Accepted Manuscript
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    Colorless polyimides derived from 2R, 5R, 7S, 10S-naphthanetetracarboxylic dianhydride

    X. Hu, J. Yan, Y. Wang, H. Mu, Z. wang, H. Cheng, F. Zhao and Z. Wang, Polym. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7PY01048F

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