Synthesis of Chiral Polyphenylenes through Bergman Cyclization of Enediynes with Pendant Chiral Amino Ester Groups

Shiyuan Sun; Binlei Huang; Fei Li; Depeng Song; Aiguo Hu

doi:10.1007/s10118-015-1622-2

Your Location：

Home >

Browse articles >

Synthesis of Chiral Polyphenylenes through Bergman Cyclization of Enediynes with Pendant Chiral Amino Ester Groups

PAPER | Updated：2021-06-21

- Synthesis of Chiral Polyphenylenes through Bergman Cyclization of Enediynes with Pendant Chiral Amino Ester Groups
- Synthesis of Chiral Polyphenylenes through Bergman Cyclization of Enediynes with Pendant Chiral Amino Ester Groups
- Chinese Journal of Polymer Science 2015年33卷第5期页码：743-753
- Affiliations：
  
  Shanghai Key Laboratory of Advanced Polymeric Materials, School of Materials Science and Engineering, East China University of Science and Technology, Shanghai 200237, China
- Author bio：
  
  **Aiguo Hu (胡爱国), E-mail: hagmhsn@ecust.edu.cn
- Funds：
  
  National Natural Science Foundation of China(21474027;91023008);Ph. D. Programs Foundation of Ministry of Education of China(20100074110002);Fundamental Research Funds for the Central Universities, Shanghai Leading Academic Discipline Project(B502)
- DOI：10.1007/s10118-015-1622-2
  中图分类号：
- 收稿：2014-09-10，
  
  修回：2014-09-28，
  
  录用：2014-09-29，
  
  纸质出版：2015-05
- Accepted：
Scan QR Code
Shiyuan Sun, Binlei Huang, Fei Li, 等. Synthesis of Chiral Polyphenylenes through Bergman Cyclization of Enediynes with Pendant Chiral Amino Ester Groups[J]. Chinese Journal of Polymer Science, 2015,33(5):743-753.

Shiyuan Sun, Binlei Huang, Fei Li, et al. Synthesis of Chiral Polyphenylenes through Bergman Cyclization of Enediynes with Pendant Chiral Amino Ester Groups[J]. Chinese Journal of Polymer Science, 2015, 33(5): 743-753.
Shiyuan Sun, Binlei Huang, Fei Li, 等. Synthesis of Chiral Polyphenylenes through Bergman Cyclization of Enediynes with Pendant Chiral Amino Ester Groups[J]. Chinese Journal of Polymer Science, 2015,33(5):743-753. DOI： 10.1007/s10118-015-1622-2.

Shiyuan Sun, Binlei Huang, Fei Li, et al. Synthesis of Chiral Polyphenylenes through Bergman Cyclization of Enediynes with Pendant Chiral Amino Ester Groups[J]. Chinese Journal of Polymer Science, 2015, 33(5): 743-753. DOI： 10.1007/s10118-015-1622-2.

摘要

Abstract

Chiral enediynes with pendant chiral amino ester groups are synthesized through Sonogashira reactions and subjected to thermal triggered Bergman cyclization at elevated temperatures either in bulk or in solvents to produce chiral polyphenylenes. The disappearance of enediyne monomers are evidenced by FTIR and NMR spectroscopies. The formation of polyphenylenes is further confirmed by UV-Vis and MALDI-TOF mass spectroscopies (MS). Isotope pattern analysis of the MS spectra shows that the polymers prepared in solvents are terminated by the solvent molecules

whereas the chain ends of the polymers prepared in bulk consist of considerable amount of unmasked free radicals

which is further confirmed by EPR analysis. Circular dichroism (CD) spectra of the chiral polymers show blue shifts of the Cotton peaks

indicating the occurrence of the cycloaromatization reaction. A new set of peaks mirrored at the horizontal axis show up in the long wavelength range

which are assigned to main chain chirality of the polyphenylenes.

关键词

Keywords

references

浏览量

159

Downloads

CSCD

文章被引用时，请邮件提醒。

Submit

工具集

关联资源

Palladium-catalyzed Cycloaromatization Polymerization of Enediynes

Synthesis of Polyphenylenes through Bergman Cyclization of Enediynes with Long Chain Alkyl Groups

Highly Regio- and trans-Selective Ring-opening Metathesis Polymerization of Chiral Aza-norbornene with a Simple Phenylimido-Tungsten Catalyst

End-to-End Neuron-inspired Signal Transduction Using Organic Electrochemical Transistors

Advances in Polymer-based Circularly Polarized Luminescent Materials