Advertisement

Colloid and Polymer Science

, Volume 297, Issue 4, pp 661–666 | Cite as

CO2-responsive behavior of polymer giant vesicles supporting hindered amine

  • Eri YoshidaEmail author
Short Communication
  • 60 Downloads

Abstract

The CO2-responsive behavior of giant vesicles supporting hindered amines on the shells was investigated with the aim of reversible control of the self-assembly. The investigation was carried out using vesicles consisting of poly(2,2,6,6-tetramethyl-4-piperidyl methacrylate)-block-poly(methyl methacrylate-random-2,2,6,6-tetramethyl-4-piperidyl methacrylate), PTPMA55-b-P(MMA0.977-r-TPMA0.023)321, in an aqueous methanol solution. As CO2 was introduced into the vesicle solution, the electroconductivity and transmittance increased whereas the scattering intensity and hydrodynamic diameter for the light scattering measurements decreased due to the dissociation of the vesicles into micelles based on the protonation of the hindered amines on the shells. The introduction of Ar instead of CO2 produced inverse changes in these factors based on the aggregation of the micelles due to the deprotonation. The vesicles showed a good hysteresis for the cycles of the CO2-Ar introduction. It was found that the dissociation-aggregation of the vesicles was reversibly controlled by the alternate CO2-Ar introduction.

Graphical Abstract

Keywords

Giant vesicles Hindered amines CO2-responsive behavior Amphiphilic block copolymer Protonation-deprotonation Alternate CO2-Ar introduction Reversible control of self-assembly 

Notes

Funding information

This work was supported by the JSPS Grant-in-Aid for Scientific Research (Grant Number 18K04863).

Compliance with ethical standards

Conflict of interest

The author declares that there is no conflict of interest.

References

  1. 1.
    Qin S, Geng Y, Discher DE, Yang S (2006) Temperature-controlled assembly and release from polymer vesicles of poly(ethylene oxide)-block-poly(N-isopropylacrylamide). Adv Mater 18:2905–2909CrossRefGoogle Scholar
  2. 2.
    Tanner P, Baumann P, Enea R, Onaca O, Palivan C, Meier W (2011) Polymeric vesicles: from drug carriers to nanoreactors and artificial organelles. Acc Chem Res 44:1039–1049CrossRefGoogle Scholar
  3. 3.
    Li Y, Lokitz BS, McCormick CL (2006) Thermally responsive vesicles and their structural “locking” through polyelectrolyte complex formation. Angew Chem Int Ed 45:5792–5795CrossRefGoogle Scholar
  4. 4.
    Yan Q, Yuan J, Yuan W, Zhou M, Yin Y, Pan C (2008) Copolymer logical switches adjusted through core–shell micelles: from temperature response to fluorescence response. Chem Commun 2008:6188–6190CrossRefGoogle Scholar
  5. 5.
    Pasparakis G, Alexander C (2008) Sweet talking double hydrophilic block copolymer vesicles. Angew Chem Int Ed 47:4847–4850CrossRefGoogle Scholar
  6. 6.
    Yoshida E, Ohta M, Terada Y (2005) Reversible control of micellization induced by hydrogen bond crosslinking for a nonamphiphilic diblock copolymer with an α,ω-diamine. Polym Adv Technol 16:183–188CrossRefGoogle Scholar
  7. 7.
    Shen H, Zhang L, Eisenberg A (1999) Multiple pH-induced morphological changes in aggregates of polystyrene-block-poly(4-vinylpyridine) in DMF/H2O mixtures. J Am Chem Soc 121:2728–2740CrossRefGoogle Scholar
  8. 8.
    Rodrı’guez-Herna’ndez J, Lecommandoux S (2005) Reversible inside-out micellization of pH-responsive and water-soluble vesicles based on polypeptide diblock copolymers. J Am Chem Soc 127:2026–2027CrossRefGoogle Scholar
  9. 9.
    Klaikherd A, Nagamani C, Thayumanavan S (2009) Multi-stimuli sensitive amphiphilic block copolymer assemblies. J Am Chem Soc 131:4830–4838CrossRefGoogle Scholar
  10. 10.
    McClain JB, Canelas DA, Samulski ET, DeSimone JM, Londono JD, Cochran HD, Wignall GD, Chillura-Martino GD, Triolo R (1996) Design of nonionic surfactants for supercritical carbon dioxide. Science 274:2049–2052CrossRefGoogle Scholar
  11. 11.
    Zhou S, Chu B (1998) Laser light scattering study of pressure-induced micellization of a diblock copolymer of poly(1,1-dihydroperfluorooctylacrylate) and poly(vinyl acetate) in supercritical carbon dioxide. Macromolecules 31:5300–5308CrossRefGoogle Scholar
  12. 12.
    Celso L, Triolo A, Triolo F, Donato DI, Steinhart M, Kriechbaum M, Amenitsch H, Triolo R (2002) SAXS investigation on aggregation phenomena in supercritical CO2. Eur Phys J E 8:311–314CrossRefGoogle Scholar
  13. 13.
    Ueki T, Nakamura Y, Lodge TP, Watanabe M (2012) Light-controlled reversible micellization of a diblock copolymer in an ionic liquid. Macromolecules 45:7566–7573CrossRefGoogle Scholar
  14. 14.
    Chen W, Du J (2013) Ultrasound and pH dually responsive polymer vesicles for anticancer drug delivery. Sci Rep 3:2162CrossRefGoogle Scholar
  15. 15.
    Yan Q, Yuan J, Cai Z, Xin Y, Kang Y, Yin Y (2010) Voltage-responsive vesicles based on orthogonal assembly of two homopolymers. J Am Chem Soc 132:9268–9270CrossRefGoogle Scholar
  16. 16.
    Napoli A, Valentini M, Tirelli N, Müller M, Hubbell JA (2004) Oxidation-responsive polymeric vesicles. Nat Mater 3:183–189CrossRefGoogle Scholar
  17. 17.
    Power-Billard KN, Spontak RJ, Manners I (2004) Redox-active organometallic vesicles: aqueous self-assembly of a diblock copolymer with a hydrophilic polyferrocenylsilane polyelectrolyte block. Angew Chem Int Ed 43:1260–1260CrossRefGoogle Scholar
  18. 18.
    Yoshida E, Tanaka T (2006) Oxidation-induced micellization of a diblock copolymer containing stable nitroxyl radicals. Colloid Polym Sci 285:135–144CrossRefGoogle Scholar
  19. 19.
    Yoshida E, Tanaka T (2008) Reduction-induced micellization of a diblock copolymer containing stable nitroxyl radicals. Colloid Polym Sci 286:827–830CrossRefGoogle Scholar
  20. 20.
    Yoshida E, Ogawa H (2007) Micelle formation induced by disproportionation of stable nitroxyl radicals supported on a diblock copolymer. J Oleo Sci 56:297–302CrossRefGoogle Scholar
  21. 21.
    Ma N, Li Y, Xu H, Wang Z, Zhang X (2010) Dual redox responsive assemblies formed from diselenide block copolymers. J Am Chem Soc 132:442–443CrossRefGoogle Scholar
  22. 22.
    Jiang J, Tong X, Zhao Y (2005) A new design for light-breakable polymer micelles. J Am Chem Soc 127:8290–8291CrossRefGoogle Scholar
  23. 23.
    Yoshida E, Kuwayama S (2007) Micelle formation induced by photolysis of a poly(tert-butoxystyrene)-block-polystyrene diblock copolymer. Colloid Polym Sci 285:1287–1291CrossRefGoogle Scholar
  24. 24.
    Yoshida E, Kuwayama S (2009) Micelle formation induced by photo-Claisen rearrangement of poly(4-allyloxystyrene)-block-polystyrene. Colloid Polym Sci 287:789–793CrossRefGoogle Scholar
  25. 25.
    Han D, Boissiere O, Kumar S, Tong X, Tremblay L, Zhao Y (2012) Two-way CO2-switchable triblock copolymer hydrogels. Macromolecules 45:7440–7445CrossRefGoogle Scholar
  26. 26.
    Jing X, Huang Z, Lu H, Wang B (2017) Use of a hydrophobic accosiative four-armed star anionic polymer to create a saline aqueous solution of CO2-switchability. J Dispers Sci Technol 38:1698–1704CrossRefGoogle Scholar
  27. 27.
    Pinaud J, Kowal E, Cunningham M, Jessop P (2012) 2-(Diethyl)aminoethyl methacrylate as a CO2-switchable comonomer for the preparation of readily coagulated and redispersed polymer latexes. ACS Macro Lett 1:1103–1107CrossRefGoogle Scholar
  28. 28.
    Zhang Q, Yu G, Wang W, Li B, Zhu S (2012) Preparation of CO2/N2-triggered reversibly coagulatable and redispersible polyacrylate latexes by emulsion polymerization using a polymeric surfactant. Macromol Rapid Commun 33:916–921CrossRefGoogle Scholar
  29. 29.
    Zou H, Yuan W (2015) CO2- and thermo-responsive vesicles: from expansion-contraction transformation to vesicles-micelles transition. Polym Chem 6:2457–2465CrossRefGoogle Scholar
  30. 30.
    Yan Q, Zhao Y (2013) Polymeric microtubules that breathe: CO2-driven polymer controlled-self-assembly and shape transformation. Angew Chem Int Ed 52:9948–9951CrossRefGoogle Scholar
  31. 31.
    Yan Q, Zhou R, Fu C, Zhang H, Yin Y, Yuan J (2011) CO2-responsive polymeric vesicles that breathe. Angew Chem Int Ed 50:4923–4927CrossRefGoogle Scholar
  32. 32.
    Liu G, Wang X, Hu J, Zhang G, Liu S (2014) Self-immolative polymersomes for high-efficiency triggered release and programmed enzymatic reactions. J Am Chem Soc 136:7492–7497CrossRefGoogle Scholar
  33. 33.
    Haas S, Hain N, Raoufi M, Handschuh-Wang S, Wang T, Jiang X, Schönherr H (2015) Enzyme degradable polymersomes from hyaluronic acid-block-poly(ε-caprolactone) copolymers for the detection of enzymes of pathogenic bacteria. Biomacromolecules 16:832–841CrossRefGoogle Scholar
  34. 34.
    Scherer M, Kappel C, Mohr N, Fischer K, Heller P, Forst R, Depoix F, Bros M, Zentel R (2016) Functionalization of active ester-based polymersomes for enhanced cell uptake and stimuli-responsive cargo release. Biomacromolecules 17:3305–3317CrossRefGoogle Scholar
  35. 35.
    Zhou X, Su X, Zhou C (2018) Preparation of diblock amphiphilic polypeptide nanoparticles for medical applications. Eur Polym J 100:132–136CrossRefGoogle Scholar
  36. 36.
    Yoshida E (2013) Giant vesicles prepared by nitroxide-mediated photo-controlled/living radical polymerization-induced self-assembly. Colloid Polym Sci 291:2733–2739CrossRefGoogle Scholar
  37. 37.
    Yoshida E (2015) Fabrication of microvillus-like structure by photopolymerization-induced self-assembly of an amphiphilic random block copolymer. Colloid Polym Sci 293:1841–1845CrossRefGoogle Scholar
  38. 38.
    Yoshida E (2017) Fabrication of anastomosed tubular networks developed out of fenestrated sheets through thermo responsiveness of polymer giant vesicles. ChemXpress 10(1):118Google Scholar
  39. 39.
    Yoshida E (2016) Worm-like vesicle formation by photo-controlled/living radical polymerization-induced self-assembly of amphiphilic poly(methacrylic acid)-block-poly(methyl methacrylate-random-methacrylic acid). Colloid Polym Sci 294:1857–1863CrossRefGoogle Scholar
  40. 40.
    Yoshida E (2015) Morphological changes in polymer giant vesicles by intercalation of a segment copolymer as a sterol model in plasma membrane. Colloid Polym Sci 29:1835–1840CrossRefGoogle Scholar
  41. 41.
    Yoshida E (2018) Morphology transformation of giant vesicles by a polyelectrolyte for an artificial model of a membrane protein for endocytosis. Colloid Surf Sci 3(1):6–11CrossRefGoogle Scholar
  42. 42.
    Yoshida E (2014) Fission of giant vesicles accompanied by hydrophobic chain growth through polymerization-induced self-assembly. Colloid Polym Sci 292:1463–1468CrossRefGoogle Scholar
  43. 43.
    Yoshida E (2015) Enhanced permeability of Rhodamine B into bilayers comprised of amphiphilic random block copolymers by incorporation of ionic segments in the hydrophobic chains. Colloid Polym Sci 293:2437–2443CrossRefGoogle Scholar
  44. 44.
    Yoshida E (2015) PH response behavior of giant vesicles comprised of amphiphilic poly(methacrylic acid)-block-poly(methyl methacrylate-random-methacrylic acid). Colloid Polym Sci 293:649–653CrossRefGoogle Scholar
  45. 45.
    Yoshida E (2018) Photo nitroxide-mediated living radical polymerization of hindered amine-supported methacrylate. J Res Update Polym Sci 7:21–28CrossRefGoogle Scholar
  46. 46.
    Effendy JPC, Kepert CJ, Louis LM, Morien TC, Skelton BW, White AH (2006) The structural systematics of protonation of some important nitrogen-base ligands. III Some (univalent) anion salts of some hindered unidentate nitrogen bases. Z Anorg Allg Chem 632:1312–1325CrossRefGoogle Scholar
  47. 47.
    Kurosaki T, Lee KW, Okawara M (1972) Polymers having stable radicals. I. Synthesis of nitroxyl polymers from 4-methacryloyl derivatives of 2,2,6,6-tetramethylpiperidine. J Polym Sci, Polym Chem Ed 10:3295–3310Google Scholar
  48. 48.
    Bojinov V, Grabchev I (2002) Synthesis and properties of new adducts of 2,2,6,6-tetramethylpiperidine and 2-hydroxyphenylbenzotriazole as polymer photostabilizers. J Photochem Photobiol A Chem 150:223–231CrossRefGoogle Scholar
  49. 49.
    Blair VL, Carrella LM, Clegg W, Conway B, Harrington RW, Hogg LM, Klett J, Mulvey RE, Rentschler E, Russo L (2008) Tuning the basicity of synergic bimetallic reagents: switching the regioselectivity of the direct dimetalation of toluene from 2,5- to 3,5-positions. Angew Chem Int Ed 47:6208–6211CrossRefGoogle Scholar
  50. 50.
    Yoshida E, Kunugi S (2002) Micelle formation of nonamphiphilic diblock copolymers through noncovalent bond cross-linking. Macromolecules 35:6665–6669CrossRefGoogle Scholar
  51. 51.
    Ye X, Li ZW, Sun ZY, Khomami B (2016) Template-free bottom-up method for fabricating diblock copolymer patchy particles. ACS Nano 10:5199–5203CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Department of Environmental and Life SciencesToyohashi University of TechnologyToyohashiJapan

Personalised recommendations