Skip to main content
Erschienen in: Cellulose 7/2018

17.05.2018 | Original Paper

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

verfasst von: Junji Xuan, Jintao Tian

Erschienen in: Cellulose | Ausgabe 7/2018

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

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.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Anhänge
Nur mit Berechtigung zugänglich
Literatur
Zurück zum Zitat Abdollahi A, Rad JK, Mahdavian AR (2016) Stimuli-responsive cellulose modified by epoxy-functionalized polymer nanoparticles with photochromic and solvatochromic properties. Carbohydr Polym 150:131–138CrossRefPubMed Abdollahi A, Rad JK, Mahdavian AR (2016) Stimuli-responsive cellulose modified by epoxy-functionalized polymer nanoparticles with photochromic and solvatochromic properties. Carbohydr Polym 150:131–138CrossRefPubMed
Zurück zum Zitat 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 106:2232–2236CrossRef 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 106:2232–2236CrossRef
Zurück zum Zitat 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 8:744–751CrossRefPubMed 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 8:744–751CrossRefPubMed
Zurück zum Zitat Chen L, Wu J, Schmuck C, Tian H (2014b) A switchable peptide sensor for real-time lysosomal tracking. Chem Commun 50:6443–6446CrossRef Chen L, Wu J, Schmuck C, Tian H (2014b) A switchable peptide sensor for real-time lysosomal tracking. Chem Commun 50:6443–6446CrossRef
Zurück zum Zitat Fissi A, Pieroni O, Ruggeri G, Ciardelli F (1995) Photoresponsive polymers. Photomodulation of the macromolecular structure in poly (L-lysine) containing spiropyran units. Macromolecules 28:302–309CrossRef Fissi A, Pieroni O, Ruggeri G, Ciardelli F (1995) Photoresponsive polymers. Photomodulation of the macromolecular structure in poly (L-lysine) containing spiropyran units. Macromolecules 28:302–309CrossRef
Zurück zum Zitat Gericke M, Trygg J, Fardim P (2013) Functional cellulose beads: preparation, characterization, and applications. Chem Rev 113:4812–4836CrossRefPubMed Gericke M, Trygg J, Fardim P (2013) Functional cellulose beads: preparation, characterization, and applications. Chem Rev 113:4812–4836CrossRefPubMed
Zurück zum Zitat 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 117:13561–13571CrossRefPubMedPubMedCentral 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 117:13561–13571CrossRefPubMedPubMedCentral
Zurück zum Zitat Hu W, Liu S, Chen S, Wang H (2011) Preparation and properties of photochromic bacterial cellulose nanofibrous membranes. Cellulose 18:655–661CrossRef Hu W, Liu S, Chen S, Wang H (2011) Preparation and properties of photochromic bacterial cellulose nanofibrous membranes. Cellulose 18:655–661CrossRef
Zurück zum Zitat Hufendiek A, Barner-Kowollik C, Meier MAR (2015) Renewable, fluorescent, and thermoresponsive: cellulose copolymers via light-induced ligation in solution. Polym Chem 6:2188–2191CrossRef Hufendiek A, Barner-Kowollik C, Meier MAR (2015) Renewable, fluorescent, and thermoresponsive: cellulose copolymers via light-induced ligation in solution. Polym Chem 6:2188–2191CrossRef
Zurück zum Zitat Johns VK, Wang Z, Li X, Liao Y (2013) Physicochemical study of a metastable-state photoacid. J Phys Chem A 117:13101–13104CrossRefPubMed Johns VK, Wang Z, Li X, Liao Y (2013) Physicochemical study of a metastable-state photoacid. J Phys Chem A 117:13101–13104CrossRefPubMed
Zurück zum Zitat 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 43:7217–7235CrossRefPubMed 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 43:7217–7235CrossRefPubMed
Zurück zum Zitat 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 134:14070–14077CrossRefPubMed 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 134:14070–14077CrossRefPubMed
Zurück zum Zitat Kumari S, Chauhan GS (2014) New cellulose–lysine schiff-base-based sensor–adsorbent for mercury ions. ACS Appl Mater Interfaces 6:5908–5917CrossRefPubMed Kumari S, Chauhan GS (2014) New cellulose–lysine schiff-base-based sensor–adsorbent for mercury ions. ACS Appl Mater Interfaces 6:5908–5917CrossRefPubMed
Zurück zum Zitat 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 5:9161–9166CrossRefPubMed 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 5:9161–9166CrossRefPubMed
Zurück zum Zitat 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 17:25676–25688CrossRefPubMed 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 17:25676–25688CrossRefPubMed
Zurück zum Zitat 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 417:179–182CrossRef 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 417:179–182CrossRef
Zurück zum Zitat Nilsson JR, Li S, Onfelt B, Andreasson J (2011) Light-induced cytotoxicity of a photochromic spiropyran. Chem Commun 47:11020–11022CrossRef Nilsson JR, Li S, Onfelt B, Andreasson J (2011) Light-induced cytotoxicity of a photochromic spiropyran. Chem Commun 47:11020–11022CrossRef
Zurück zum Zitat 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 12:209–236CrossRef 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 12:209–236CrossRef
Zurück zum Zitat Pinkert A, Marsh KN, Pang S, Staiger MP (2009) Ionic liquids and their interaction with cellulose. Chem Rev 109:6712–6728CrossRefPubMed Pinkert A, Marsh KN, Pang S, Staiger MP (2009) Ionic liquids and their interaction with cellulose. Chem Rev 109:6712–6728CrossRefPubMed
Zurück zum Zitat Rad JK, Mahdavian AR (2016) Preparation of fast photoresponsive cellulose and kinetic study of photoisomerization. J Phys Chem C 120:9985–9991CrossRef Rad JK, Mahdavian AR (2016) Preparation of fast photoresponsive cellulose and kinetic study of photoisomerization. J Phys Chem C 120:9985–9991CrossRef
Zurück zum Zitat 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 88:56–66CrossRef 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 88:56–66CrossRef
Zurück zum Zitat Roy D, Semsarilar M, Guthrie JT, Perrier S (2009) Cellulose modification by polymer grafting: a review. Chem Soc Rev 38:2046–2064CrossRefPubMed Roy D, Semsarilar M, Guthrie JT, Perrier S (2009) Cellulose modification by polymer grafting: a review. Chem Soc Rev 38:2046–2064CrossRefPubMed
Zurück zum Zitat 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 4:8676–8681CrossRef 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 4:8676–8681CrossRef
Zurück zum Zitat 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 105:66–74CrossRef 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 105:66–74CrossRef
Zurück zum Zitat Tian W, Tian J (2014b) Synergy of different fluorescent enhancement effects on spiropyran appended onto cellulose. Langmuir 30:3223–3227CrossRefPubMed Tian W, Tian J (2014b) Synergy of different fluorescent enhancement effects on spiropyran appended onto cellulose. Langmuir 30:3223–3227CrossRefPubMed
Zurück zum Zitat 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 133:5453–5462CrossRefPubMed 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 133:5453–5462CrossRefPubMed
Zurück zum Zitat Wang H, Gurau G, Rogers RD (2012) Ionic liquid processing of cellulose. Chem Soc Rev 41:1519–1537CrossRefPubMed Wang H, Gurau G, Rogers RD (2012) Ionic liquid processing of cellulose. Chem Soc Rev 41:1519–1537CrossRefPubMed
Zurück zum Zitat Wang B, Chen K, Yang R, Yang F, Liu J (2014) Stimulus-responsive polymeric micelles for the light-triggered release of drugs. Carbohydr Polym 103:510–519CrossRefPubMed Wang B, Chen K, Yang R, Yang F, Liu J (2014) Stimulus-responsive polymeric micelles for the light-triggered release of drugs. Carbohydr Polym 103:510–519CrossRefPubMed
Zurück zum Zitat 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 119:20762–20772CrossRef 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 119:20762–20772CrossRef
Zurück zum Zitat 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 7:2607–2615CrossRefPubMed 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 7:2607–2615CrossRefPubMed
Zurück zum Zitat 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 128:4303–4309CrossRefPubMedPubMedCentral 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 128:4303–4309CrossRefPubMedPubMedCentral
Zurück zum Zitat 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 47:1543–1552CrossRef 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 47:1543–1552CrossRef
Metadaten
Titel
Preparation of cellulose colloidal particles in aqueous solution with good photochromic and photoluminescent performances by grafting a spiropyran derivative onto filter paper cellulose
verfasst von
Junji Xuan
Jintao Tian
Publikationsdatum
17.05.2018
Verlag
Springer Netherlands
Erschienen in
Cellulose / Ausgabe 7/2018
Print ISSN: 0969-0239
Elektronische ISSN: 1572-882X
DOI
https://doi.org/10.1007/s10570-018-1844-x

Weitere Artikel der Ausgabe 7/2018

Cellulose 7/2018 Zur Ausgabe