Skip to main content
Log in

Conformational chirality of the biphenyl groups induced by the aggregation of poly{bis[4-(4’-(S)-2-methylbutoxy)-biphenoxy] phosphazene}

  • Organic materials
  • Published:
Journal of Wuhan University of Technology-Mater. Sci. Ed. Aims and scope Submit manuscript

Abstract

Poly{bis[4-(4’-(S)-2-methylbutoxy)biphenyloxy]phosphazene}(PP-C) was designed and successfully synthesized, and then characterized by means of FT-IR spectroscopy, 1H- and 31P-NMR, GPC spectroscopy, wide angle X-ray diffraction and differential scanning calorimetry. The results indicated that for PP-C, the M w is 2.18×105 and the PDI is 1.96. PP-C was a kind of crystallized polymer with a crystallizing point of -2.0 °C and a melting point of 28 °C. The conformational chirality of the PP-C molecules was studied using circular dichroism spectrum. It was found that in dilute THF solution, the biphenyl groups in the PP-C molecules twisted randomly. However, when the PP-C formed aggregates, the biphenyl groups tended to twist single-handedly, which was controlled by the adjacent chiral alkoxy groups.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Fujiki M. Optically Active Polysilylenes: State of the Art Chiroptical Polymers[J]. Macromol. Rapid Commun., 2001, 22(8): 539–563

    Article  Google Scholar 

  2. Nolte R J M, Van Beijnen A J M, Drenth W. Chirality in Polyisocyanides[J]. J. Am. Chem. Soc., 1974, 96(18): 5932–5933

    Article  Google Scholar 

  3. Okamoto Y, Suzuki K, Ohta K, et al. Optically Active Poly(triphenylm ethylmethacrylate) with One-Handed Helical Conformation[J]. J. Am. Chem. Soc., 1979, 101(16): 4763–4765

    Article  Google Scholar 

  4. Goodman M, Chen S. Optically Active Polyisocyanates. II[J]. Macromolecules, 1971, 4(5): 625–629

    Article  Google Scholar 

  5. Pino P, Ciardelli F, Montagnoli G, et al. On the Relationship between Monomer Optical Purity and Polymer Rrotatory Power in Some Linear Poly-a-olefines[J]. J. Polym. Sci., Part B: Polym. Lett. Ed., 1967, 5(4): 307–311

    Article  Google Scholar 

  6. Yashima E, Maeda K, Okamoto Y. Memory of Macromolecular Helicity Assisted by Interaction with Achiral Small Molecules[J]. Nature, 1999, 399: 449–451

    Article  Google Scholar 

  7. Saxena A, Guo G, Fujiki M, et al. Helical Polymer Command Surface: Thermodriven Chiroptical Transfer and Amplification in Binary Polysilane Film System[J]. Macromolecules, 2004, 37(9): 3081–3083

    Article  Google Scholar 

  8. Allcock H R. Poly(organophosphazenes)-Unusual New High Polymers[J]. Angew. Chem., Int. Ed., 1977, 16(3): 147–156

    Article  Google Scholar 

  9. Allcock H R. Polyphosphazenes: New Polymers with Inorganic Backbone Atoms[J]. Science, 1976, 193(4259): 1214–1219

    Article  Google Scholar 

  10. Lin Y, Deng Q, Jin R. Effects of Processing Variables on the Morphology and Diameter of Electrospun Poly(amino acid ester) phosphazene Nanofibers[J]. Journal of Wuhan University of Technology-Mater. Sci. Ed., 2012, 27(2): 207–211

    Article  Google Scholar 

  11. Allcock H R. Polyphosphazene Elastomers, Gels, and Other Soft Materials[J]. Soft Matter., 2012, 8(8): 7521–7532

    Article  Google Scholar 

  12. Yashima E, Maeda K, Yamanaka T. Helicity Induction and Conformational Dynamics of Poly(bis(4-carboxyphenoxy) phosphazene) with Optically Active Amines[J]. J. Am. Chem. Soc., 2000, 122(32): 7813–7814

    Article  Google Scholar 

  13. MacQuarrie S, Thompson M P, Blanc A, et al. Chiral Periodic Mesoporous Organosilicates Based on Axially Chiral Monomers: Transmission of Chirality in the Solid State[J]. J. Am. Chem. Soc., 2008, 130(43): 14099–14101

    Article  Google Scholar 

  14. Li B, Xu Z, Zhuang W, et al. Characterization of 4,4’-Bipheny-lenesilicas and a Chiral Sensor for Silicas[J]. Chem. Commun., 2011, 47(41): 11495–11497

    Article  Google Scholar 

  15. D’Halluin G, De Jaeger R, Chambrette J P, et al. Synthesis of Poly(dichlorophosphazenes) from Cl3P=NP(O)Cl2. Kinetics and Reaction Mechanism[J]. Macromolecules, 1992, 25(4): 1254–1258

    Article  Google Scholar 

  16. Guo Y, Li B, Yang Y, et al. Synthesis and Mesomorphic Properties of Some Chiral Fluorinated Benzoates[J]. Mol. Cryst. Liq. Cryst., 2008, 493(493): 57–64

    Article  Google Scholar 

  17. Wang R, Li X, Bai J, et al. Chiroptical and Thermotropic Properties of Helical Styrenic Polymers: Effect of Achiral Group[J]. Macromolecules, 2014, 47(5): 1553–1562

    Article  Google Scholar 

  18. He M, Zhang H, Chen W, et al. Polymer Physics: Third Edition[M]. Shanghai: Fudan University Press, 2007

    Google Scholar 

  19. Chen C, Zhang B, Chen F. A Novel Method for Calculating Starch Crystallinity[J]. Food Science, 2011, 32(9): 68–71

    Google Scholar 

  20. Bortolus P, Gleria M. Photochemistry and Photophysics of Poly (organophosphazenes) and Related Compounds: A Review. I. Monomolecular Processes[J]. J. Inorg. Organomet. Polym., 1994, 4(1): 1–29

    Article  Google Scholar 

  21. Deng J, Luo X, Zhao W, et al. A Novel Type of Optically Active Helical Polymers: Synthesis and Characterization of Poly(N-propargylureas) [J]. Journal of Polymer Science: Part A: Polymer Chemistry, 2008, 46(12): 4112–4121

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yi Li  (李艺).

Additional information

Funded by the National Natural Science Foundation of China (No.21274098)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tang, X., Li, B., Li, Y. et al. Conformational chirality of the biphenyl groups induced by the aggregation of poly{bis[4-(4’-(S)-2-methylbutoxy)-biphenoxy] phosphazene}. J. Wuhan Univ. Technol.-Mat. Sci. Edit. 31, 1162–1166 (2016). https://doi.org/10.1007/s11595-016-1506-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11595-016-1506-5

Keywords

Navigation