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Reversible photoswitching aggregation and dissolution of spiropyranfunctionalized copolymer and light-responsive FRET process

Lei-Xiao Yu ,  Yang Liu ,  Si-Chong Chen ,  Yue Guan ,  Yu-Zhong Wang

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Citation:  Lei-Xiao Yu, Yang Liu, Si-Chong Chen, Yue Guan, Yu-Zhong Wang. Reversible photoswitching aggregation and dissolution of spiropyranfunctionalized copolymer and light-responsive FRET process[J]. Chinese Chemical Letters, 2014, 25(3): 389-396. doi: 10.1016/j.cclet.2013.12.014 shu

Reversible photoswitching aggregation and dissolution of spiropyranfunctionalized copolymer and light-responsive FRET process

    • 通讯作者: Si-Chong Chen,
    Yu-Zhong Wang,
  • 基金项目:

    Innovative Research Team in University of Ministry of Education of China (No. IRT1026). (No. IRT1026)

摘要: Well-defined, reversibly light-responsive amphiphilic diblock copolymer grafted with spiropyran, was prepared by reversible addition-fragmentation chain transfer (RAFT) polymerization. The copolymer self-assembles into polymeric micelles in water and exhibits reversible dissolution and re-aggregation characteristics upon ultraviolet (UV) and visible (Vis)-light irradiation. The fluorescence response of spiropyran immobilized onto the copolymer was light switchable. When nitrobenzoxadiazolyl derivative (NBD) dyes are encapsulated into the core of the micelles, a reversible, light-responsive, dual-color fluorescence resonance energy transfer (FRET) system is constructed and processed, which is well regulated by alternatively UV/vis irradiation. We anticipate these photoswitchable and FRET lighting up nanoparticles will be useful in drug delivery and cell imaging or tracking synchronously.

English

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    1. [1] Y.L. Yu, M. Nakano, T. Ikeda, Photomechanics: directed bending of a polymer film by light, Nature 425 (2003) 145.[1] Y.L. Yu, M. Nakano, T. Ikeda, Photomechanics: directed bending of a polymer film by light, Nature 425 (2003) 145.

    2. [2] H. Lee, W. Wu, J.K. Oh, et al., Light-induced reversible formation of polymeric micelles, Angew. Chem. Int. Ed. 46 (2007) 2453-2457.[2] H. Lee, W. Wu, J.K. Oh, et al., Light-induced reversible formation of polymeric micelles, Angew. Chem. Int. Ed. 46 (2007) 2453-2457.

    3. [3] V.K. Kotharangannagari, A. Sànchez-Ferrer, J. Ruokolainen, R. Mezzenga, Photoresponsive reversible aggregation and dissolution of rod-coil polypeptide diblock copolymers, Macromolecules 44 (2011) 4569-4573.[3] V.K. Kotharangannagari, A. Sànchez-Ferrer, J. Ruokolainen, R. Mezzenga, Photoresponsive reversible aggregation and dissolution of rod-coil polypeptide diblock copolymers, Macromolecules 44 (2011) 4569-4573.

    4. [4] S. Dai, P. Ravi, K.C. Tam, pH-responsive polymers: synthesis, properties and applications, Soft Matter 4 (2008) 435-449.[4] S. Dai, P. Ravi, K.C. Tam, pH-responsive polymers: synthesis, properties and applications, Soft Matter 4 (2008) 435-449.

    5. [5] S. Yusa, M. Sugahara, T. Endo, Y. Morishima, Preparation and characterization of a pH-responsive nanogel based on a photo-cross-linked micelle formed from block copolymers with controlled structure, Langmuir 25 (2009) 5258-5265.[5] S. Yusa, M. Sugahara, T. Endo, Y. Morishima, Preparation and characterization of a pH-responsive nanogel based on a photo-cross-linked micelle formed from block copolymers with controlled structure, Langmuir 25 (2009) 5258-5265.

    6. [6] G. Wu, S.C. Chen, Q. Zhan, Y.Z. Wang, Well-defined amphiphilic biodegradable comb-like graft copolymers: their unique architecture-determined LCST and UCST thermoresponsivity, Macromolecules 44 (2011) 999-1008.[6] G. Wu, S.C. Chen, Q. Zhan, Y.Z. Wang, Well-defined amphiphilic biodegradable comb-like graft copolymers: their unique architecture-determined LCST and UCST thermoresponsivity, Macromolecules 44 (2011) 999-1008.

    7. [7] A.P. Vogt, B.S. Sumerlin, Temperature and redox responsive hydrogels from ABA triblock copolymers prepared by RAFT polymerization, Soft Matter 5 (2009) 2347-2351.[7] A.P. Vogt, B.S. Sumerlin, Temperature and redox responsive hydrogels from ABA triblock copolymers prepared by RAFT polymerization, Soft Matter 5 (2009) 2347-2351.

    8. [8] J.M. Hu, G.Y. Zhang, Y.H. Geng, S.Y. Liu, Micellar nanoparticles of coil-rod-coil triblock copolymers for highly sensitive and ratiometric fluorescent detection of fluoride Ions, Macromolecules 44 (2011) 8207-8214.[8] J.M. Hu, G.Y. Zhang, Y.H. Geng, S.Y. Liu, Micellar nanoparticles of coil-rod-coil triblock copolymers for highly sensitive and ratiometric fluorescent detection of fluoride Ions, Macromolecules 44 (2011) 8207-8214.

    9. [9] C.J. Chen, Q. Jin, G.Y. Liu, et al., Reversibly light-responsive micelles constructed via a simple modification of hyperbranched polymers with chromophores, Polymer 53 (2012) 3695-3703.[9] C.J. Chen, Q. Jin, G.Y. Liu, et al., Reversibly light-responsive micelles constructed via a simple modification of hyperbranched polymers with chromophores, Polymer 53 (2012) 3695-3703.

    10. [10] C.Q. Huang, Y. Wang, C.Y. Hong, C.Y. Pan, Spiropyran-based polymeric vesicles: preparation and photochromic properties, Macromol. Rapid Commun. 32 (2011) 1174-1179.[10] C.Q. Huang, Y. Wang, C.Y. Hong, C.Y. Pan, Spiropyran-based polymeric vesicles: preparation and photochromic properties, Macromol. Rapid Commun. 32 (2011) 1174-1179.

    11. [11] C.S. Brazel, Magnetothermally-responsive nanomaterials: combining magnetic nanostructures and thermally-sensitive polymers for triggered drug release, Pharm. Res. 26 (2009) 644-656.[11] C.S. Brazel, Magnetothermally-responsive nanomaterials: combining magnetic nanostructures and thermally-sensitive polymers for triggered drug release, Pharm. Res. 26 (2009) 644-656.

    12. [12] M. Irie, Photoresponsive polymers. Reversible bending of rod-shaped acrylamide gels in an electric field, Macromolecules 19 (1986) 2890-2892.[12] M. Irie, Photoresponsive polymers. Reversible bending of rod-shaped acrylamide gels in an electric field, Macromolecules 19 (1986) 2890-2892.

    13. [13] H.T.T. Duong, C.P. Marquis, M. Whittaker, T.P. Davis, C. Boyer, Acid degradable and biocompatible polymeric nanoparticles for the potential codelivery of therapeutic agents, Macromolecules 44 (2011) 8008-8019.[13] H.T.T. Duong, C.P. Marquis, M. Whittaker, T.P. Davis, C. Boyer, Acid degradable and biocompatible polymeric nanoparticles for the potential codelivery of therapeutic agents, Macromolecules 44 (2011) 8008-8019.

    14. [14] Y.H. Wang, M. Zheng, F.H. Meng, et al., Branched polyethylenimine derivatives with reductively cleavable periphery for safe and efficient in vitro gene transfer, Biomacromolecules 12 (2011) 1032-1040.[14] Y.H. Wang, M. Zheng, F.H. Meng, et al., Branched polyethylenimine derivatives with reductively cleavable periphery for safe and efficient in vitro gene transfer, Biomacromolecules 12 (2011) 1032-1040.

    15. [15] T.A. Darwish, R.A. Evans, M. James, et al., CO2 triggering and controlling orthogonally multiresponsive photochromic systems, J. Am. Chem. Soc. 132 (2010) 10748-10755.[15] T.A. Darwish, R.A. Evans, M. James, et al., CO2 triggering and controlling orthogonally multiresponsive photochromic systems, J. Am. Chem. Soc. 132 (2010) 10748-10755.

    16. [16] D.H. Han, X. Tong, O. Boissière, Y. Zhao, General strategy for making CO2-switchable polymers, ACS Macro Lett. 1 (2012) 57-61.[16] D.H. Han, X. Tong, O. Boissière, Y. Zhao, General strategy for making CO2-switchable polymers, ACS Macro Lett. 1 (2012) 57-61.

    17. [17] J.P. Magnusson, A. Khan, G. Pasparakis, et al., Ion-sensitive "isothermal" responsive polymers prepared in water, J. Am. Chem. Soc. 130 (2008) 10852-10853.[17] J.P. Magnusson, A. Khan, G. Pasparakis, et al., Ion-sensitive "isothermal" responsive polymers prepared in water, J. Am. Chem. Soc. 130 (2008) 10852-10853.

    18. [18] D.B. Liu, W.W. Chen, K. Sun, et al., Resettable, multi-readout logic gates based on controllably reversible aggregation of gold nanoparticles, Angew. Chem. Int. Ed. 50 (2011) 4103-4107.[18] D.B. Liu, W.W. Chen, K. Sun, et al., Resettable, multi-readout logic gates based on controllably reversible aggregation of gold nanoparticles, Angew. Chem. Int. Ed. 50 (2011) 4103-4107.

    19. [19] M. Irie, T. Fukaminato, T. Sasaki, N. Tamai, T. Kawai, Organic chemistry: a digital fluorescent molecular photoswitch, Nature 420 (2002) 759-760.[19] M. Irie, T. Fukaminato, T. Sasaki, N. Tamai, T. Kawai, Organic chemistry: a digital fluorescent molecular photoswitch, Nature 420 (2002) 759-760.

    20. [20] Y.M. Li, Y.F. Qian, T. Liu, G.Y. Zhang, S.Y. Liu, Light-triggered concomitant enhancement of magnetic resonance imaging contrast performance and drug release rate of functionalized amphiphilic diblock copolymer micelles, Biomacromolecules 13 (2012) 3877-3886.[20] Y.M. Li, Y.F. Qian, T. Liu, G.Y. Zhang, S.Y. Liu, Light-triggered concomitant enhancement of magnetic resonance imaging contrast performance and drug release rate of functionalized amphiphilic diblock copolymer micelles, Biomacromolecules 13 (2012) 3877-3886.

    21. [21] S. Wang, Y. Song, L.J. Jiang, Photoresponsive surfaces with controllable wettability, Photochem. Photobiol. C 8 (2007) 18-29.[21] S. Wang, Y. Song, L.J. Jiang, Photoresponsive surfaces with controllable wettability, Photochem. Photobiol. C 8 (2007) 18-29.

    22. [22] M.Q. Zhu, G.F. Zhang, C. Li, et al., Reversible two-photon photoswitching and twophoton imaging of immunofunctionalized nanoparticles targeted to cancer cells, J. Am. Chem. Soc. 133 (2011) 365-372.[22] M.Q. Zhu, G.F. Zhang, C. Li, et al., Reversible two-photon photoswitching and twophoton imaging of immunofunctionalized nanoparticles targeted to cancer cells, J. Am. Chem. Soc. 133 (2011) 365-372.

    23. [23] A. Nayak, H. Liu, G. Belfort, An optically reversible switching membrane surface, Angew. Chem. Int. Ed. 45 (2006) 4094-4098.[23] A. Nayak, H. Liu, G. Belfort, An optically reversible switching membrane surface, Angew. Chem. Int. Ed. 45 (2006) 4094-4098.

    24. [24] Y. Zhao, Light-responsive block copolymer micelles, Macromolecules 45 (2012) 3647-3657.[24] Y. Zhao, Light-responsive block copolymer micelles, Macromolecules 45 (2012) 3647-3657.

    25. [25] X.K. Liu, M. Jiang, Optical switching of self-assembly: micellization and micellehollow-sphere transition of hydrogen-bonded polymers, Angew. Chem. Int. Ed. 45 (2006) 3846-3850.[25] X.K. Liu, M. Jiang, Optical switching of self-assembly: micellization and micellehollow-sphere transition of hydrogen-bonded polymers, Angew. Chem. Int. Ed. 45 (2006) 3846-3850.

    26. [26] L. Ming, L.Y. Gu, Q. Zhang, M.Z. Xue, Y.G. Liu, Preparation and study of photoswitchable fluorescence nanoparticles based on spirobenzopyran, Chin. Chem. Lett. 24 (2013) 1014-1018.[26] L. Ming, L.Y. Gu, Q. Zhang, M.Z. Xue, Y.G. Liu, Preparation and study of photoswitchable fluorescence nanoparticles based on spirobenzopyran, Chin. Chem. Lett. 24 (2013) 1014-1018.

    27. [27] J.L. Mynar, A.P. Goodwin, J.A. Cohen, et al., Two-photon degradable supramolecular assemblies of linear-dendritic copolymers, Chem. Commun. 20 (2007) 2081-2082.[27] J.L. Mynar, A.P. Goodwin, J.A. Cohen, et al., Two-photon degradable supramolecular assemblies of linear-dendritic copolymers, Chem. Commun. 20 (2007) 2081-2082.

    28. [28] D.H. Han, X. Tong, Y. Zhao, Fast photodegradable block copolymer micelles for burst release, Macromolecules 44 (2011) 437-439.[28] D.H. Han, X. Tong, Y. Zhao, Fast photodegradable block copolymer micelles for burst release, Macromolecules 44 (2011) 437-439.

    29. [29] Y. Zhao, J. Bertrand, X. Tong, Y. Zhao, Photo-cross-linkable polymer micelles in hydrogen-bonding-built layer-by-layer films, Langmuir 25 (2009) 13151-13157.[29] Y. Zhao, J. Bertrand, X. Tong, Y. Zhao, Photo-cross-linkable polymer micelles in hydrogen-bonding-built layer-by-layer films, Langmuir 25 (2009) 13151-13157.

    30. [30] J.T. Lai, D. Filla, R. Shea, Functional polymers from novel carboxyl-terminated trithiocarbonates as highly efficient RAFT agents, Macromolecules 35 (2002) 6754-6756.[30] J.T. Lai, D. Filla, R. Shea, Functional polymers from novel carboxyl-terminated trithiocarbonates as highly efficient RAFT agents, Macromolecules 35 (2002) 6754-6756.

    31. [31] D.J. Chung, Y. Ito, Y. Imanishi, Preparation of porous membranes grafted with poly (spiropyran-containing methacrylate) and photocontrol of permeability, J. Appl. Polym. Sci. 51 (1994) 2027-2033.[31] D.J. Chung, Y. Ito, Y. Imanishi, Preparation of porous membranes grafted with poly (spiropyran-containing methacrylate) and photocontrol of permeability, J. Appl. Polym. Sci. 51 (1994) 2027-2033.

    32. [32] S.I. Yusa, Y. Yokoyama, Y. Morishima, Synthesis of oppositely charged block copolymers of poly(ethylene glycol) via reversible addition-fragmentation chain transfer radical polymerization and characterization of their polyion complex micelles in water, Macromolecules 42 (2009) 376-383.[32] S.I. Yusa, Y. Yokoyama, Y. Morishima, Synthesis of oppositely charged block copolymers of poly(ethylene glycol) via reversible addition-fragmentation chain transfer radical polymerization and characterization of their polyion complex micelles in water, Macromolecules 42 (2009) 376-383.

    33. [33] Y.K. Chong, J. Krstina, T.P.T. Le, et al., Thiocarbonylthio compounds [SC(Ph)S-R] in free radical polymerization with reversible addition-fragmentation chain transfer (RAFT polymerization). Role of the free-radical leaving group (R), Macromolecules 36 (2003) 2256-2272.[33] Y.K. Chong, J. Krstina, T.P.T. Le, et al., Thiocarbonylthio compounds [SC(Ph)S-R] in free radical polymerization with reversible addition-fragmentation chain transfer (RAFT polymerization). Role of the free-radical leaving group (R), Macromolecules 36 (2003) 2256-2272.

    34. [34] Y. Cao, X.X. Zhu, J.T. Luo, H.Y. Liu, Effects of substitution groups on the RAFT polymerization of N-alkylacrylamides in the preparation of thermosensitive block copolymers, Macromolecules 40 (2007) 6481-6488.[34] Y. Cao, X.X. Zhu, J.T. Luo, H.Y. Liu, Effects of substitution groups on the RAFT polymerization of N-alkylacrylamides in the preparation of thermosensitive block copolymers, Macromolecules 40 (2007) 6481-6488.

    35. [35] K. Sumaru, M. Kameda, T. Kanamori, T. Shinbo, Characteristic phase transition of aqueous solution of poly (N-isopropylacrylamide) functionalized with spirobenzopyran, Macromolecules 37 (2004) 4949-4955.[35] K. Sumaru, M. Kameda, T. Kanamori, T. Shinbo, Characteristic phase transition of aqueous solution of poly (N-isopropylacrylamide) functionalized with spirobenzopyran, Macromolecules 37 (2004) 4949-4955.

    36. [36] A.Y. Bobrovsky, N.I. Boiko, V.P. Shibaev, Photosensitive cholesteric copolymers with spiropyran-containing side groups: novel materials for optical data recording, Adv. Mater. 11 (1999) 1025-1028.[36] A.Y. Bobrovsky, N.I. Boiko, V.P. Shibaev, Photosensitive cholesteric copolymers with spiropyran-containing side groups: novel materials for optical data recording, Adv. Mater. 11 (1999) 1025-1028.

    37. [37] D.S. Achilleos, M. Vamvakaki, Multiresponsive spiropyran-based copolymers synthesized by atom transfer radical polymerization, Macromolecules 43 (2010) 7073-7081.[37] D.S. Achilleos, M. Vamvakaki, Multiresponsive spiropyran-based copolymers synthesized by atom transfer radical polymerization, Macromolecules 43 (2010) 7073-7081.

    38. [38] M. Piech, N.S. Bell, Controlled synthesis of photochromic polymer brushes by atom transfer radical polymerization, Macromolecules 39 (2006) 915-922.[38] M. Piech, N.S. Bell, Controlled synthesis of photochromic polymer brushes by atom transfer radical polymerization, Macromolecules 39 (2006) 915-922.

    39. [39] G.Y. Jiang, Y.L. Song, X.F. Guo, D.Q. Zhang, D.B. Zhu, Organic functional molecules towards information processing and high-density information storage, Adv. Mater. 20 (2008) 2888-2898.[39] G.Y. Jiang, Y.L. Song, X.F. Guo, D.Q. Zhang, D.B. Zhu, Organic functional molecules towards information processing and high-density information storage, Adv. Mater. 20 (2008) 2888-2898.

    40. [40] M.Q. Zhu, L.Y. Zhu, J.J. Han, et al., Spiropyran-based photochromic polymer nanoparticles with optically switchable luminescence, J. Am. Chem. Soc. 128 (2006) 4303-4309.[40] M.Q. Zhu, L.Y. Zhu, J.J. Han, et al., Spiropyran-based photochromic polymer nanoparticles with optically switchable luminescence, J. Am. Chem. Soc. 128 (2006) 4303-4309.

    41. [41] D.S. Achilleos, T.A. Hatton, M. Vamvakaki, Light-regulated supramolecular engineering of polymeric nanocapsules, J. Am. Chem. Soc. 134 (2012) 5726-5729.[41] D.S. Achilleos, T.A. Hatton, M. Vamvakaki, Light-regulated supramolecular engineering of polymeric nanocapsules, J. Am. Chem. Soc. 134 (2012) 5726-5729.

    42. [42] K.E. Sapsford, L. Berti, I.L. Medintz, Materials for fluorescence resonance energy transfer analysis: beyond traditional donor-acceptor combinations, Angew. Chem. Int. Ed. 45 (2006) 4562-4589.[42] K.E. Sapsford, L. Berti, I.L. Medintz, Materials for fluorescence resonance energy transfer analysis: beyond traditional donor-acceptor combinations, Angew. Chem. Int. Ed. 45 (2006) 4562-4589.

    43. [43] Y. Wang, C.Y. Hong, C.Y. Pan, Spiropyran-based hyperbranched star copolymer: synthesis, phototropy, FRET, and bioapplication, Biomacromolecules 13 (2012) 2585-2593.[43] Y. Wang, C.Y. Hong, C.Y. Pan, Spiropyran-based hyperbranched star copolymer: synthesis, phototropy, FRET, and bioapplication, Biomacromolecules 13 (2012) 2585-2593.

    44. [44] J. Chen, F. Zeng, S.Z. Wu, Q.M. Chen, Z. Tong, A core-shell nanoparticle approach to photoreversible fluorescence modulation of a hydrophobic dye in aqueous media, Chem. Eur. J. 14 (2008) 4851-4860.[44] J. Chen, F. Zeng, S.Z. Wu, Q.M. Chen, Z. Tong, A core-shell nanoparticle approach to photoreversible fluorescence modulation of a hydrophobic dye in aqueous media, Chem. Eur. J. 14 (2008) 4851-4860.

    45. [45] J. Föling, S. Polyakova, V. Belov, et al., Synthesis and characterization of photoswitchable fluorescent silica nanoparticles, Small 4 (2008) 134-142.[45] J. Föling, S. Polyakova, V. Belov, et al., Synthesis and characterization of photoswitchable fluorescent silica nanoparticles, Small 4 (2008) 134-142.

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  • 发布日期:  2013-12-24
  • 收稿日期:  2013-11-11
  • 网络出版日期:  2013-12-06
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