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Preparation of cellulose colloidal particles in aqueous solution with good photochromic and photoluminescent performances by grafting a spiropyran derivative onto filter paper cellulose

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Abstract

The cellulose colloidal particles with good photochromic and photoluminescent performances had been developed in aqueous solution based on a spiropyran-grafted filter paper cellulose (SP–cellulose) in this study. The insoluble filter paper cellulose dramatically became soluble in ethanol after grafting a spiropyran derivative onto its backbone via esterification. During this process, the optical properties of the spiropyran had been successfully inherited. With the aid of ultraviolet and visible light, the obtained SP–cellulose colloidal particles showed light-induced tunability on both photochromism and photoluminescence, corresponding to the significant change of the spiropyran between weak polar ring-closed spiropyran and strong polar ring-opened zwitterionic merocyanine. Based upon this result, the SP–cellulose colloidal particles were finally obtained in water by follow-up dialysis process. In comparison to the pure spiropyran showing poor optical properties in mixed solvent of ethanol/water, the obtained SP–cellulose colloidal particles in water showed good photochromic and photoluminescent performances as well as fine stability. Considering also the raw material of filter paper being cheap and easy to get as well as the facile preparation process of the functional colloidal particles, our experimental results may bring about more promising applications of spiropyran species and water-insoluble cellulose in aqueous medium.

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References

  • Abdollahi A, Rad JK, Mahdavian AR (2016) Stimuli-responsive cellulose modified by epoxy-functionalized polymer nanoparticles with photochromic and solvatochromic properties. Carbohydr Polym 150:131–138

    Article  CAS  PubMed  Google Scholar 

  • Bletz M, Pfeifer-Fukumura U, Kolb U, Baumann W (2002) Ground-and first-excited-singlet-state electric dipole moments of some photochromic spirobenzopyrans in their spiropyran and merocyanine form. J Phys Chem A 106:2232–2236

    Article  CAS  Google Scholar 

  • Chen L, Wang W, Su B, Wen Y, Li C, Zhou Y, Li M, Shi X, Du H, Song Y, Jiang L (2014a) A light-responsive release platform by controlling the wetting behavior of hydrophobic surface. ACS Nano 8:744–751

    Article  CAS  PubMed  Google Scholar 

  • Chen L, Wu J, Schmuck C, Tian H (2014b) A switchable peptide sensor for real-time lysosomal tracking. Chem Commun 50:6443–6446

    Article  CAS  Google Scholar 

  • Fissi A, Pieroni O, Ruggeri G, Ciardelli F (1995) Photoresponsive polymers. Photomodulation of the macromolecular structure in poly (L-lysine) containing spiropyran units. Macromolecules 28:302–309

    Article  CAS  Google Scholar 

  • Gericke M, Trygg J, Fardim P (2013) Functional cellulose beads: preparation, characterization, and applications. Chem Rev 113:4812–4836

    Article  CAS  PubMed  Google Scholar 

  • Hammarson M, Nilsson J, Li S, Beke-Somfai T, Andréasson J (2013) Characterization of the thermal and photoinduced reactions of photochromic spiropyrans in aqueous solution. J Phys Chem B 117:13561–13571

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Hu W, Liu S, Chen S, Wang H (2011) Preparation and properties of photochromic bacterial cellulose nanofibrous membranes. Cellulose 18:655–661

    Article  CAS  Google Scholar 

  • Hufendiek A, Barner-Kowollik C, Meier MAR (2015) Renewable, fluorescent, and thermoresponsive: cellulose copolymers via light-induced ligation in solution. Polym Chem 6:2188–2191

    Article  CAS  Google Scholar 

  • Johns VK, Wang Z, Li X, Liao Y (2013) Physicochemical study of a metastable-state photoacid. J Phys Chem A 117:13101–13104

    Article  CAS  PubMed  Google Scholar 

  • Joubert F, Musa OM, Hodgson DR, Cameron NR (2014) The preparation of graft copolymers of cellulose and cellulose derivatives using ATRP under homogeneous reaction conditions. Chem Soc Rev 43:7217–7235

    Article  CAS  PubMed  Google Scholar 

  • Klajn R (2014) Spiropyran-based dynamic materials. Chem Soc Rev 43:148–184

    Article  CAS  PubMed  Google Scholar 

  • Kohl-Landgraf J, Braun M, Özçoban C, Gonçalves DP, Heckel A, Wachtveitl J (2012) Ultrafast dynamics of a spiropyran in water. J Am Chem Soc 134:14070–14077

    Article  CAS  PubMed  Google Scholar 

  • Kumari S, Chauhan GS (2014) New cellulose–lysine schiff-base-based sensor–adsorbent for mercury ions. ACS Appl Mater Interfaces 6:5908–5917

    Article  CAS  PubMed  Google Scholar 

  • Li YJ, Tseng YT, Unnikrishnan B, Huang CC (2013) Gold-nanoparticles-modified cellulose membrane coupled with laser desorption/ionization mass spectrometry for detection of iodide in urine. ACS Appl Mater Interfaces 5:9161–9166

    Article  CAS  PubMed  Google Scholar 

  • Markworth PB, Adamson BD, Coughlan NJA, Goerigk L, Bieske EJ (2015) Photoisomerization action spectroscopy: flicking the protonated merocyanine–spiropyran switch in the gas phase. Phys Chem Chem Phys 17:25676–25688

    Article  CAS  PubMed  Google Scholar 

  • Mi W, Tian W, Tian J, Jia J, Liu X, Dai J, Wang X (2013) Synthesis of CdSe quantum dots in ethanol: a facile way to achieve photoluminescence with high brightness. Coll Surf A 417:179–182

    Article  CAS  Google Scholar 

  • Nilsson JR, Li S, Onfelt B, Andreasson J (2011) Light-induced cytotoxicity of a photochromic spiropyran. Chem Commun 47:11020–11022

    Article  CAS  Google Scholar 

  • Paramonov SV, Lokshin V, Fedorova OA (2011) Spiropyran, chromene or spirooxazine ligands: insights into mutual relations between complexing and photochromic properties. J Photochem Photobiol C 12:209–236

    Article  CAS  Google Scholar 

  • Pinkert A, Marsh KN, Pang S, Staiger MP (2009) Ionic liquids and their interaction with cellulose. Chem Rev 109:6712–6728

    Article  CAS  PubMed  Google Scholar 

  • Rad JK, Mahdavian AR (2016) Preparation of fast photoresponsive cellulose and kinetic study of photoisomerization. J Phys Chem C 120:9985–9991

    Article  CAS  Google Scholar 

  • Rad JK, Mahdavian AR (2017) Photoswitchable dual-color fluorescent particles from seeded emulsion polymerization and role of some affecting parameters on FRET process. Eur Polym J 88:56–66

    Article  CAS  Google Scholar 

  • Roy D, Semsarilar M, Guthrie JT, Perrier S (2009) Cellulose modification by polymer grafting: a review. Chem Soc Rev 38:2046–2064

    Article  CAS  PubMed  Google Scholar 

  • Schiphorst J, Broek M, Koning T, Murphy JN, Schenning APHJ, Esteves ACC (2016) Dual light and temperature responsive cotton fabric functionalized with a surface-grafted spiropyran–NIPAAm-hydrogel. J Mater Chem A 4:8676–8681

    Article  Google Scholar 

  • Tian W, Tian J (2014a) An insight into the solvent effect on photo-, solvato-chromism of spiropyran through the perspective of intermolecular interactions. Dyes Pigment 105:66–74

    Article  CAS  Google Scholar 

  • Tian W, Tian J (2014b) Synergy of different fluorescent enhancement effects on spiropyran appended onto cellulose. Langmuir 30:3223–3227

    Article  CAS  PubMed  Google Scholar 

  • Wagner K, Byrne R, Zanoni M, Gambhir S, Dennany L, Breukers R, Higgins M, Wagner P, Diamond D, Wallace GG, Officer DL (2011) A multiswitchable poly (terthiophene) bearing a spiropyran functionality: understanding photo-and electrochemical control. J Am Chem Soc 133:5453–5462

    Article  CAS  PubMed  Google Scholar 

  • Wang H, Gurau G, Rogers RD (2012) Ionic liquid processing of cellulose. Chem Soc Rev 41:1519–1537

    Article  CAS  PubMed  Google Scholar 

  • Wang B, Chen K, Yang R, Yang F, Liu J (2014) Stimulus-responsive polymeric micelles for the light-triggered release of drugs. Carbohydr Polym 103:510–519

    Article  CAS  PubMed  Google Scholar 

  • Xue Y, Tian J, Tian W, Gong P, Dai J, Wang X (2015) Significant fluorescence enhancement of spiropyran in colloidal dispersion and its light-induced size tunability for release control. J Phys Chem C 119:20762–20772

    Article  CAS  Google Scholar 

  • Zhao J, Lu C, He H, Zhang X, Zhang W (2015) Polyethylenimine-grafted cellulose nanofibril aerogels as versatile vehicles for drug delivery. ACS Appl Mater Interfaces 7:2607–2615

    Article  CAS  PubMed  Google Scholar 

  • Zhu MQ, Zhu L, Han JJ, Wu W, Hurst JK, Li AD (2006) Spiropyran-based photochromic polymer nanoparticles with optically switchable luminescence. J Am Chem Soc 128:4303–4309

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Zhu MQ, Zhang GF, Hu Z, Aldred MP, Li C, Gong WL, Chen T, Huang ZL, Liu S (2014) Reversible fluorescence switching of spiropyran-conjugated biodegradable nanoparticles for super-resolution fluorescence imaging. Macromolecules 47:1543–1552

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work is financially supported by the Natural Science Foundation of Shandong Province of China (ZR2018MB011).

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Correspondence to Jintao Tian.

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10570_2018_1844_MOESM1_ESM.docx

The synthetic process, FTIR spectrum, and 1H NMR spectrum of the SP–COOH, GPC data of the SP–Cellulose, details of calculation about the grafting rate and the degree of substitution of the SP–Cellulose, relative fluorescence quantum yield of SP–COOH and SP–cellulose samples in different solvents, and other supplementary data are given (DOCX 1050 kb)

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Xuan, J., Tian, J. Preparation of cellulose colloidal particles in aqueous solution with good photochromic and photoluminescent performances by grafting a spiropyran derivative onto filter paper cellulose. Cellulose 25, 4067–4078 (2018). https://doi.org/10.1007/s10570-018-1844-x

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  • DOI: https://doi.org/10.1007/s10570-018-1844-x

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