Abstract
Wholly aromatic polyketones 7 containing bisbinaphthyl macrocycles were synthesized via P2O5-MsOH mediated direct condensation reaction of compound 3 with chlorobenzoic acids 4, nucleophilic aromatic substitution reaction of the resulting binaphthyl (5) with (S)-BINOL (1) in DMF/toluene, and NiBr2/Zn mediated aromatic coupling polymerization. The resulting polyketones 7 have excellent thermal resistance and solubility to organic solvents. Cyclic monomers 6 and polymers 7 have higher molar rotations based on optically active cyclic structures than pre-cyclized compounds 5.
Similar content being viewed by others
Log in or create a free account to read this content
Gain free access to this article, as well as selected content from this journal and more on nature.com
or
References
R. Noyori, Chem. Soc. Rev., 18, 187 (1989).
Y. Yamashita, H. Ishitani, H. Shimizu, and S. Kobayashi, J. Am. Chem. Soc., 124, 3292 (2002).
T. Akiyama, J. Itoh, K. Yokota, and K. Fuchibe, Angew. Chem., Int. Ed., 43, 1566 (2004).
Q. S. Hu, X.-F. Zheng, and L. Pu, J. Org. Chem., 61, 5200 (1996).
S. Habaue, T. Seko, and Y. Okamoto, Macromolecules, 35, 2437 (2002).
G. Koeckelberghs, S. Sioncke, T. Verbiest, I. V. Severen, I. Picard, A. Persoons, and C. Samyn, Macromolecules, 36, 9736 (2003).
F. Kondo, D. Takahashi, H. Kimura, and M. Takeishi, Polym. J., 30, 161 (1998).
T. Takata, Y. Furusho, K. Murakawa, T. Endo, H. Matsuoka, T. Hirasa, J. Matsuo, and M. Sisido, J. Am. Chem. Soc., 120, 4530 (1998).
K. Maeyama, I. Hikiji, K. Ogura, A. Okamoto, K. Ogino, H. Saito, and N. Yonezawa, Polym. J., 37, 707 (2005).
K. Maeyama, K. Ogura, A. Okamoto, K. Ogino, H. Saito, and N. Yonezawa, Polym. J., 37, 736 (2005).
K. Maeyama, S. Maeda, K. Ogino, H. Saito, and N. Yonezawa, React. Funct. Polym., 65, 229 (2005).
D. J. Cram and J. M. Cram, Science, 183, 803, (1974).
D. S. Lingenfelter, R. C. Helgeson, and D. J. Cram, J. Org, Chem., 46, 393, (1981).
H. Cao, X. Liu, T. Ben, C. Chen, Z. Gao, and W. Zhang, Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.), 43, 1112 (2002).
G. Dang, W. Yang, X. Zhao, C. Chen, F. Li, W. Zhang, and Z. Wu, Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.), 44, 911 (2003).
X. Wang, N. Liu, H. Cao, W. Liu, C. Chen, W. Zhang, and Y. Wei, Macromol. Rapid Commun., 26, 554 (2005).
N. Liu, X. Wang, E. Jin, C. Chen, W. Zhang, and Y. Wei, Polymer, 47, 3021 (2006).
S. Maeda, K. Maeyama, and N. Yonezawa, Synth. Commun., accepted.
P. E. Eaton and G. R. Carlson, J. Org. Chem., 38, 4071 (1973).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Maeyama, K., Maeda, S., Saito, H. et al. Synthesis of Wholly Aromatic Polyketones Containing Optically Active Macrocycles. Polym J 39, 342–346 (2007). https://doi.org/10.1295/polymj.PJ2006159
Received:
Accepted:
Published:
Issue date:
DOI: https://doi.org/10.1295/polymj.PJ2006159
