Skip to main content
SpringerLink
Log in

Photo-responsive supramolecular polymer based on a CB[5] analogue

  • Short Communication
  • Published:
Colloid and Polymer Science Aims and scope Submit manuscript

Abstract

A supramolecular polymer was constructed in aqueous solution via the intermolecular recognition between a cucurbit[5]uril-like macrocycle (Me10TD[5]) and trans-4,4′-bis(aminomethyl)azobenzene dihydrochloride, whose binding behaviors were confirmed by proton nuclear magnetic resonance (1H NMR), isothermal titration calorimetry (ITC) and electrospray ionization mass spectrometry (ESI-MS) experiments. The resulting polymer exhibited bending/extending behaviors under alternative UV light irradiations due to the trans/cis isomerization of the azobenzene group. The photo-responsive performance of the polymer was investigated by UV–Vis, transmission electron microscopy (TEM), and dynamic light scattering (DLS) measurements.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4

References

  1. Chen S, Mahmood N, Beiner M, Binder WH (2015) Self-healing materials from V- and H-shaped supramolecular architectures. Angew Chem 127:1–6

    Article  Google Scholar 

  2. Dai X, Zhang Y, Gao L, Bai T, Wang W, Cui Y, Liu W (2015) A mechanically strong, highly stable, thermoplastic, and self-healable supramolecular polymer hydrogel. Adv Mater 27:3566–3571

    Article  CAS  Google Scholar 

  3. Zhang M, Xu D, Yan X, Chen J, Dong S, Zheng B, Huang F (2012) Self-healing supramolecular gels formed by crown ether based host–guest interactions. Angew Chem 124:7117–7121

    Article  Google Scholar 

  4. Zhang H, Fan X, Suo R, Li H, Yang Z, Zhang W, Bai Y, Yao H, Tian W (2015) Reversible morphology transitions of supramolecular polymer self-assemblies for switch-controlled drug release. Chem Commun 51:15366–15369

    Article  CAS  Google Scholar 

  5. Szente L, Puskás I, Csabai K, Éva F (2014) Supramolecular proteoglycan aggregate mimics: cyclodextrin-assisted biodegradable polymer assemblies for electrostatic-driven drug delivery. Chem Asian J 9:1365–1372

    Article  CAS  Google Scholar 

  6. Freeman R, Boekhoven J, Dickerson MB, Naik RR, Stupp SI (2015) Biopolymers and supramolecular polymers as biomaterials for biomedical applications. MRS Bull 40:1089–1101

    Article  CAS  Google Scholar 

  7. Luo Q, Dong Z, Houa C, Liu J (2014) Protein-based supramolecular polymers: progress and prospect. Chem Commun 50:9997–10007

    Article  CAS  Google Scholar 

  8. Yao X, Li T, Wang S, Ma X, Tian H (2014) A photochromic supramolecular polymer based on bis-p-sulfonatocalix[4]arene recognition in aqueous solution. Chem Commun 50:7166–7168

    Article  CAS  Google Scholar 

  9. Liu X, Xu JF, Wang Z, Zhang X (2016) Photo-responsive supramolecular polymers synthesized by olefin metathesis polymerization from supramonomers. Polym Chem 7:2333–2336

    Article  CAS  Google Scholar 

  10. Zhang S, Bellinger AM, Glettig DL, Barman R, Lee YA, Zhu J, Cleveland C, Montgomery VA, Gu L, Nash LD, Maitland DJ, Langer R, Traverso G (2015) A pH-responsive supramolecular polymer gel as an enteric elastomer for use in gastric devices. Nat Mater 14:1065–1071

    Article  CAS  Google Scholar 

  11. Yao X, Ma X, Tian H (2014) Aggregation-induced emission encoding supramolecular polymers based on controllable sulfonatocalixarene recognition in aqueous solution. J Mater Chem 2:5155–5160

    CAS  Google Scholar 

  12. Zhou Y, Jie K, Shia B, Yao Y (2015) A γ-ray and dual redox-responsive supramolecular polymer constructed by a selenium containing pillar[5]arene dimer and a neutral guest. Chem Commun 51:11112–11114

    Article  CAS  Google Scholar 

  13. Guo W, Lei Z (2015) Redox-responsive supramolecular polymer based on β-cyclodextrin and ferrocene-decorated main chain of PAA. J Mater Res 30:1–10

    Article  CAS  Google Scholar 

  14. Zhou M, Ye X, Liu K, Hu J, Qian X (2015) Tunable thermo-responsive supramolecular hydrogel: design, characterization, and drug release. J Polym Res 22:1–8

    Article  Google Scholar 

  15. Brassinne J, Bourgeois JP, Fustin CA, Gohy JF (2014) Thermo-responsive properties of metallo-supramolecular block copolymer micellar hydrogels. Soft Matter 10:3086–3092

    Article  CAS  Google Scholar 

  16. Ma X, Tian H (2014) Stimuli-responsive supramolecular polymers in aqueous solution. Acc Chem Res 47:1971–1981

    Article  CAS  Google Scholar 

  17. Chen Z, Wang Q, Wu X, Li Z, Jiang YB (2015) Optical chirality sensing using macrocycles, synthetic and supramolecular oligomers/polymers, and nanoparticle based sensors. Chem Soc Rev 44:4249–4263

    Article  CAS  Google Scholar 

  18. Qu D, Wang Q, Zhang Q, Ma X, Tian H (2015) Photoresponsive host–guest functional systems. Chem Rev 115:7543–7588

    Article  CAS  Google Scholar 

  19. Lagona J, Mukhopadhyay P, Chakrabarti S, Isaacs L (2005) The cucurbit[n]uril family. Angew Chem Int Ed 44:4844–4870

    Article  CAS  Google Scholar 

  20. Liu Y, Yu Y, Gao J, Wang Z, Zhang X (2010) Water-soluble supramolecular polymerization driven by multiple host-stabilized charge-transfer interactions. Angew Chem Int Ed 49:6576–6579

    Article  CAS  Google Scholar 

  21. Ni XL, Xiao X, Cong H, Zhu QJ, Xue SF, Tao Z (2014) Self-assemblies based on the “outer-surface interactions” of cucurbit[n]urils: new opportunities for supramolecular architectures and materials. Acc Chem Res 47:1386–1395

    Article  CAS  Google Scholar 

  22. Barrio J, Horton PN, Lairez D, Lloyd GO, Toprakcioglu C, Scherman OA (2013) Photocontrol over cucurbit[8]uril complexes: stoichiometry and supramolecular polymers. J Am Chem Soc 135:11760–11763

    Article  Google Scholar 

  23. Zhao J, Zhang YM, Sun HL, Chang XY, Liu Y (2014) Multistimuli-responsive supramolecular assembly of cucurbituril/cyclodextrin pairs with an azobenzene-containing bispyridinium guest. Chem Eur J 20:15108–15115

    Article  CAS  Google Scholar 

  24. Yang H, Liu Y, Liu K, Yang L, Wang Z, Zhang X (2013) Rational adjustment of multicolor emissions by cucurbiturils-based host–guest chemistry and photochemistry. Langmuir 29:12909–12914

    Article  CAS  Google Scholar 

  25. Ustrnul L, Kulhanek P, Lizal T, Sindelar V (2015) Pressocucurbit[5]uril. Org Lett 17:1022–1025

    Article  CAS  Google Scholar 

  26. Jiang X, Yao X, Huang X, Wang Q, Tian H (2015) A cucurbit[5]uril analogue from dimethylpropanediurea–formaldehyde condensation. Chem Commun 51:2890–2892

    Article  CAS  Google Scholar 

  27. Du G, Moulin E, Jouault N, Buhler E, Giuseppone N (2012) Muscle-like supramolecular polymers: integrated motion from thousands of molecular machines. Angew Chem Int Ed 51:12504–12508

    Article  CAS  Google Scholar 

  28. Lee J, Seungwhan O, Pyo J, Kim JM, Je JH (2015) A light-driven supramolecular nanowire actuator. Nanoscale 7:6457–6461

    Article  CAS  Google Scholar 

  29. Jansen K, Buschmann HJ, Wego A, Döpp D, Mayer C, Drexler HJ, Holdt HJ, Schollmeyer E (2001) Cucurbit[5]uril, decamethylcucurbit[5]uril and cucurbit[6]uril. Synthesis, solubility and amine complex formation. J. Incl Phenom Macrocycl Chem 39:357–363

    Article  CAS  Google Scholar 

  30. Zhang H, Wang Q, Liu M, Ma X, Tian H (2009) Switchable V-type [2]pseudorotaxanes. Org Lett 15:3234–3237

    Article  Google Scholar 

  31. Małgorzata WR, Paweł G (2013) Isothermal titration calorimetry (ITC) study of natural cyclodextrins inclusion complexes with drugs. J Therm Anal Calorim 111:2029–2035

    Article  Google Scholar 

  32. He M, Xu J, Chan TW, Lau RL (1996) Positive-ion electrospray-fourier transform ion cyclotron resonance mass spectra of polypeptides and proteins. Rapid Commun Mass Sp 10:897–902

    Article  CAS  Google Scholar 

  33. Feng C, Shen Z, Li Y, Gu L, Zhang Y, Lu G, Huang X (2009) PNIPAM-b-(PEA-g-PDMAEA) double-hydrophilic graft copolymer: synthesis and its application for preparation of gold nanoparticles in aqueous media. J Polym Sci Pol Chem 47:1811–1824

    Article  CAS  Google Scholar 

  34. Sun R, Xue C, Ma X, Gao M, Tian H, Li Q (2013) Light-driven linear helical supramolecular polymer formed by molecular-recognition-directed self-assembly of bis(p-sulfonatocalix[4]arene) and pseudorotaxane. J Am Chem Soc 135:5990–5993

    Article  CAS  Google Scholar 

  35. Qian H, Guo DS, Liu Y (2012) p-Sulfonatocalix[4]arene supramolecular polymers: formation by host–guest interactions and light response. Asian J Org Chem 1:155–159

    Article  Google Scholar 

Download references

Acknowledgments

This work was financially supported by the NSFC/China (21572063, 21372076) and the Science Fund for Creative Research Groups (21421004).

Author information

Authors and Affiliations

  1. Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai, 200237, People’s Republic of China

    Jiansen Liu, Xiaoqing Jiang, Xinghua Huang, Lei Zou & Qiaochun Wang

Authors
  1. Jiansen Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Xiaoqing Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Xinghua Huang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Lei Zou
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Qiaochun Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Qiaochun Wang.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Electronic supplementary material

ESM 1

(DOCX 1.06 mb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Liu, J., Jiang, X., Huang, X. et al. Photo-responsive supramolecular polymer based on a CB[5] analogue. Colloid Polym Sci 294, 1243–1249 (2016). https://doi.org/10.1007/s00396-016-3876-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00396-016-3876-9

Keywords

Search

Navigation