Advertisement

Synthesis, characterization, and self-assembly behavior of poly(m-phenylene)s with terthiophene and chiral side chains

  • Kazuhiro NakabayashiEmail author
  • Karin Fujita
Original Paper
  • 11 Downloads

Abstract

A series of novel poly(m-phenylene)s with terthiophene and/or chiral side chains have been developed to investigate the correlation between poly(m-phenylene) polymer structure and self-assembly behaviors. As a result of circular dichroism spectroscopy, a poly(m-phenylene) that alternately had terthiophene and chiral side chains exhibited the clear Cotton effect in THF, THF/methanol, and THF/acetonitrile conditions, indicating that the defined nanostructure was successfully formed by efficiently using the two interactions between side chains even in the good solvent condition. On the other hand, poly(m-phenylene)s with an irregularly sequence of terthiophene and chiral side chains did not have a capability to form the nanostructure regardless of solvent condition. These results demonstrated that an efficient usage of side chain interactions based on an alternating polymer structure was important for the formation of self-assembled nanostructure in poly(m-phenylene)s.

Keywords

Polyphenylene Conjugated polymer Self-assembly Circular dichroism 

Supplementary material

289_2018_2606_MOESM1_ESM.pdf (731 kb)
Supplementary material 1 (PDF 731 kb)

References

  1. 1.
    Lehn JM (2007) From supramolecular chemistry towards constitutional dynamic chemistry and adaptive chemistry. Chem Soc Rev 36:151–160CrossRefGoogle Scholar
  2. 2.
    Whitesides GM, Mathias JP, Seto CT (1991) Molecular self-assembly and nanochemistry: a chemical strategy for the synthesis of nanostructures. Science 254:1312–1319CrossRefGoogle Scholar
  3. 3.
    Ikkala O, Brinke GT (2002) Functional materials based on self-assembly of polymeric supramolecules. Science 295:2407–2409CrossRefGoogle Scholar
  4. 4.
    Samori P, Francke V, Müllen K, Rade JP (1999) Self-assembly of a conjugated polymer: from molecular rods to a nanoribbon architecture with molecular dimensions. Chem Eur J 5:2312–2317CrossRefGoogle Scholar
  5. 5.
    Cheng JH, Fou AF, Rubner MF (1994) Molecular self-assembly of conducting polymers. Solid Film 244:985–989CrossRefGoogle Scholar
  6. 6.
    Bai W, Lai N, Guan M, Yao R, Xu Y, Lin J (2018) Petal-effect superhydrophobic surface self-assembled from poly(p-phenylene)s. Euro Polym J 101:12–17CrossRefGoogle Scholar
  7. 7.
    Bai W, Yao R, Lai N, Shang X, Xu Y, Lin J (2018) Preparation of conjugated poly(p-phenylene) hierarchical microspheres by nonsolvent vapor self-assembly and their fluorescent detection of metal ions. React Funct Polym 122:33–41CrossRefGoogle Scholar
  8. 8.
    Oda M, Nothofer HG, Lieser G, Scherf U, Meskers SCJ, Neher D (2000) Circularly polarized electroluminescence from liquid-crystalline chiral polyfluorenes. Adv Mater 12:362–365CrossRefGoogle Scholar
  9. 9.
    Sinclair M, Moses D, Akagi K, Heeger AJ (1988) Anisotropy of the third-order nonlinear-optical susceptibility in a degenerate-ground-state conjugated polymer: trans-(CH)x. Phys Rev B 38:10724–10733CrossRefGoogle Scholar
  10. 10.
    Akagi K (2009) Helical polyacetylene: asymmetric polymerization in a chiral liquid-crystal field. Chem Rev 109:5354–5401CrossRefGoogle Scholar
  11. 11.
    Lam JWY, Tang BZ (2005) Functional polyacetylene. Acc Chem Res 38:745–754CrossRefGoogle Scholar
  12. 12.
    Nakano T, Okamoto Y (2001) Synthetic helical polymers: conformation and function. Chem Rev 101:4013–4038CrossRefGoogle Scholar
  13. 13.
    Brunsveld L, Prince RB, Meijer EW, Moore JS (2000) Conformational ordering of apolar, chiral m-phenylene ethynylene oligomers. Org Lett 2:1525–1528CrossRefGoogle Scholar
  14. 14.
    Huang YQ, Fan QL, Liu XF, Fu NN, Huang W (2010) Solvent- and pH-induced self-assembly of cationic meta-linked poly(phenylene ethynylene): effects of helix formation on amplified fluorescence quenching and förster resonance energy transfer. Langmuir 26:19120–19128CrossRefGoogle Scholar
  15. 15.
    Tan C, Pinto MR, Kose ME, Ghivariga I, Schanze KS (2004) Solvent-induced self-assembly of a meta-linked conjugated polyelectrolyte. Helix Formation, guest intercalation, and amplified quenching. Adv Mater 16:1208–1212CrossRefGoogle Scholar
  16. 16.
    Kumar RJ, MacDonald JM, Singh TB, Waddington LJ, Holmes AB (2011) Hierarchical self-assembly of semiconductor functionalized peptide α-helices and optoelectronic properties. J Am Chem Soc 133:8564–8573CrossRefGoogle Scholar
  17. 17.
    Vanormelingen W, Pandey L, Auweraer MV, Verbiest T, Koeckelberghs G (2010) Steering the conformation and chiroptical properties of poly(dithienopyrrole)s substituted with chiral OPV side chains. Macromolecules 43:2157–2168CrossRefGoogle Scholar
  18. 18.
    Kumar RJ, MacDonald JM, Singh TB, Waddington LJ, Holmes AB (2011) Hierarchical self-assembly of semiconductor functionalized peptide α-helices and optoelectronic properties. J Am Chem Soc 133:8564–8573CrossRefGoogle Scholar
  19. 19.
    Blake AJ, Cooke PA, Doyle KJ, Gair S, Simpkins NS (1998) Poly-orthophenylenes: synthesis by Suzuki coupling and solid state helical structures. Tetrahedron Lett 39:9093–9096CrossRefGoogle Scholar
  20. 20.
    Ando S, Ohta E, Kosaka A, Hashizume D, Koshino H, Fukushima T, Aida T (2012) Remarlable effects of terminal groups and solvents on helical folding of o-phenylene oligomers. J Am Chem Soc 134:11084–11087CrossRefGoogle Scholar
  21. 21.
    Ohta E, Sato H, Ando S, Kosaka A, Fukushima T, Hashizume D, Yamasaki M, Hasegawa K, Muraoka A, Ushiyama H, Yamashita K, Aida T (2011) Redox-responsive molecular helices with highly condensed π-clouds. Nat Chem 3:68–73CrossRefGoogle Scholar
  22. 22.
    Ben T, Goto H, Miwa K, Goto H, Morino K, Furusho Y, Yashima E (2008) Synthesis and helix formation of poly(m-phenylene)s bearing optically active oligo(ethylene oxide) side chains in protic media. Macromolecules 41:4506–4509CrossRefGoogle Scholar
  23. 23.
    Suda K, Akagi K (2011) Self-assembled helical conjugated poly(m-phenylene) derivatives that afford whiskers with hexagonal columnar packed structure. Macromolecules 44:9473–9488CrossRefGoogle Scholar
  24. 24.
    Leolukman M, Paoprasert P, Wang Y, Makhija V, McGee DJ, Gopalan P (2008) Influence of architecture, concentration, and thermal history on the poling of nonlinear optical chromophores in block copolymer domains. Macromolecules 41:4651–4660CrossRefGoogle Scholar
  25. 25.
    Nakabayashi K, Fujita K (2015) Unpublished workGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Graduate School of Organic Materials ScienceYamagata UniversityYonezawaJapan

Personalised recommendations