nach oben

Cellulose

Erschienen in:

01.02.2015 | Original Paper

Synthesis and characterization of azobenzene hydroxypropyl cellulose with photochromic and thermotropic liquid crystal properties

verfasst von: Wang Qin, Zhijun Li, Jixiang Li, Lihua Zhang, Ruilai Liu, Haiqing Liu

Erschienen in: Cellulose | Ausgabe 1/2015

Einloggen

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

search-config

KI-gestützte Suche

Aus

Abstract

Two types of photochromic azobenzene hydroxypropyl celluloses (azo-HPCs) are prepared by homogeneous etherification of HPC with 4-(2,3-epoxypropoxy)-azobenzene and bromoethoxy-azobenzene in N,N-dimethylacetamide under mild conditions. The degree of substitution of azo moiety of azo-HPCs is tuned in the range of 0.6–1.8 by adjusting the mole ratio of azobenzene to HPC. Their chemical structures and properties are characterized by elemental analysis, infrared spectroscopy, nuclear magnetic resonance, thermogravimetric analysis, and differential scanning calorimetry. Compared to other cellulose ethers and esters with glass transition temperature (T_g) of normally larger than 100 °C, the azo-HPC derivatives display very low T_g of ca. 20–40 °C. The azobenzenoxy-ethoxy-HPC is a thermotropic liquid crystal which displays cholesteric texture at 165 °C while cooling from its isotropic melt. Their solutions show almost fully reversible trans–cis–trans transition upon alternating irradiation of UV and visible light.

Vorheriger Artikel Modifying cellulose fibers by adsorption/precipitation of xylan

Nächster Artikel Catalytic and catalytic free process for cellulose conversion: fast pyrolysis and microwave induced pyrolysis studies

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!

Jetzt informieren

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!

Jetzt informieren

Albunia AR, Rizzo P, Coppola M, De Pascale M, Guerra G (2012) Azobenzene isomerization in polymer co-crystalline phases. Polymer 53:2727–2735CrossRef

Arai K, Shitara Y, Ohyama T (1996) Preparation of photochromic spiropyrans linked to methyl cellulose and photoregulation of their properties. J Mater Chem 6:11–14CrossRef

Asanuma H, Liang X, Nishioka H, Matsunaga D, Liu M, Komiyama M (2007) Synthesis of azobenzene-tethered DNA for reversible photo-regulation of DNA functions: hybridization and transcription. Nat Protoc 2:203–212CrossRef

Bagheri M, Shateri S (2012) Synthesis and characterization of novel liquid crystalline cholesteryl-modified hydroxypropyl cellulose derivatives. J Polym Res 19:9842–9855CrossRef

Blasco E, Barrio JD, Piñol M, Oriol L, Berges C, Sánchez C, Alcalá R (2012) Azobenzene-containing linear-dendritic block copolymers prepared by sequential ATRP and click chemistry. Polymer 53:4604–4613CrossRef

Ciardelli F, Bertoldo M, Bronco S, Pucci A, Ruggeri G, Signori F (2013) The unique optical behaviour of bio-related materials with organic chromophores. Polym Int 62:22–32CrossRef

Costa I, Filip D, Figueirinhas JL, Godinho MH (2007) New cellulose derivatives composites for electro-optical sensors. Carbohydr Polym 68:159–165CrossRef

Delbecq F, Kaneko N, Endo H, Kawai T (2012) Solvation effects with a photoresponsive two-component 12-hydroxystearic acid-azobenzene additive organogel. J Colloid Interface Sci 384:94–98CrossRef

Fan K, Bradley M, Vincent B, Faul CFJ (2011) Effect of chain length on the interaction between modified organic salts containing hydrocarbon chains and poly(N-isopropylacrylamide-co-acrylic acid) microgel particles. Langmuir 27:4362–4370CrossRef

Fritz A, Schönhals A, Sapich B, Stumpe J (1999) Dynamic and photochemical behavior of amorphous comb-like copolymers with photochromic azobenzene side groups. Macromol Chem Phys 200:2213–2220CrossRef

Gómez-Carracedo A, Alvarez-Lorenzo C, Gómez-Amoza J, Concheiro A (2003) Chemical structure and glass transition temperature of non-ionic cellulose ethers. J Therm Anal Calorim 73:587–596CrossRef

Gustafsson K, Björk M, Burreau S, Gilek M (1999) Bioaccumulation kinetics of brominated flame retardants (polybrominated diphenyl ethers) in blue mussels (Mytilus edulis). Environ Toxicol Chem 18:1218–1224CrossRef

Hancock BC, Zografi G (1994) The relationship between the glass transition temperature and the water content of amorphous pharmaceutical solids. Pharm Res 11:471–477CrossRef

Hiltunen M, Siirilä J, Maunu SL (2012) Effect of catalyst systems and reaction conditions on the synthesis of cellulose-g-PDMAam copolymers by controlled radical polymerization. J Polym Sci A Polym Chem 50:3067–3076CrossRef

Hu X, Zheng PJ, Zhao XY, Li L, Tam KC, Gan LH (2004) Preparation, characterization and novel photoregulated rheological properties of azobenzene functionalized cellulose derivatives and their α-CD complexes. Polymer 45:6219–6225CrossRef

Hu T, Xie H, Xiao J, Zhang H, Chen E (2010) Design, synthesis, and characterization of a combined main-chain/side-chain liquid-crystalline polymer based on ethyl cellulose. Cellulose 17:547–558CrossRef

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

Hurduc N, Adès D, Belleney J, Siove A, Sauvet G (2007) Photoresponsive new polysiloxanes with 4-substituted azobenzene side-groups. synthesis, characterization and kinetics of the reversible trans–cis–trans isomerization. Macromol Chem Phys 208:2600–2610CrossRef

Ifuku S, Kadla JF (2008) Preparation of a thermosensitive highly regioselective cellulose/N-isopropylacrylamide copolymer through atom transfer radical polymerization. Biomacromolecules 9:3308–3313CrossRef

Ikeda T, Mamiya J-I, Yu Y (2007) Photomechanics of liquid-crystalline elastomers and other polymers. Angew Chem Int Ed Engl 46:506–528CrossRef

Kararli TT, Hurlbut JB, Needham TE (1990) Glass–rubber transitions of cellulosic polymers by dynamic mechanical analysis. J Pharm Sci 79:845–848CrossRef

Li Z, Zhang D, Weng J, Chen B, Liu H (2014) Synthesis and characterization of photochromic azobenzene cellulose ethers. Carbohydr Polym 99:748–754CrossRef

Liu J, Ni P, Qiu D, Hou W, Zhang Q (2007) Photochromism of liquid crystalline dendrimer with azobenzene terminal groups in solution. React Funct Polym 67:416–421CrossRef

Liu S, Tan L, Li W, Li X, Chen Y (2010) Cellulose acetate nanofibers with photochromic property: fabrication and characterization. Mater Lett 64:2427–2430CrossRef

Lizu M, Lutfor MR, Surugau NL, How SE, Arshad SE (2010) Synthesis and characterization of ethylcellulose based liquid crystals containg azobenzene chromophores. Mol Cryst Liq Cryst 528:64–73CrossRef

Nechwatal A, Kosan B, Nicolai M (2013) Photochromic cellulose. AATCC Rev 13:51–57

Nicolas RC, Wilén C-E, Roth M, Pfaendner R, King RE (2006) Azoalkanes: a novel class of flame retardants. Macromol Rapid Commun 27:976–981CrossRef

Qi H, Liebert T, Heinze T (2012) Homogenous synthesis of 3-allyloxy-2-hydroxypropyl-cellulose in NaOH/urea aqueous system. Cellulose 19:925–932CrossRef

Reichardt C, Welton T (2011) Solvents and solvent effects in organic chemistry. Wiley-VCH Verlag & Co. KGaA, Weinheim

Rwei S-P, Lyu M-S, Wu P-S, Tseng C-H, Huang H-W (2009) Sol/gel transition and liquid crystal transition of HPC in ionic liquid. Cellulose 16:9–17CrossRef

Sakellariou P, Rowe R, White E (1985) The thermomechanical properties and glass transition temperatures of some cellulose derivatives used in film coating. Int J Pharm 27:267–277CrossRef

Sealey JE, Samaranayake G, Todd JG, Glasser WG (1996) Novel cellulose derivatives. IV. Preparation and thermal analysis of waxy esters of cellulose. J Polym Sci B Polym Phys 34:1613–1620CrossRef

Song Y, Sun Y, Zhang X, Zhou J, Zhang L (2008) Homogeneous quaternization of cellulose in NaOH/urea aqueous solutions as gene carriers. Biomacromolecules 9:2259–2264CrossRef

Tian WG, Tian JT (2014) Synergy of different fluorescent enhancement effects on spiropyran appended onto cellulose. Langmuir 30:3223–3227CrossRef

Wang X, Yin J, Wang X (2011) Photoinduced self-structured surface pattern on a molecular azo glass film: structure-property relationship and wavelength correlation. Langmuir 27:12666–12676CrossRef

Werbowyj RS, Gray DG (1976) Liquid crystalline structure in aqueous hydroxypropyl cellulose solutions. Mol Cryst Liq Cryst 34:97–103CrossRef

Wondraczek H, Kotiaho A, Fardim P, Heinze T (2011) Photoactive polysaccharides. Carbohydr Polym 83:1048–1061CrossRef

Yang S, Jacob MM, Li L, Cholli AL, Kumar J, Tripathy SK (2001) Synthesis and characterization of novel azobezene-modified polymers: azocellulose. Macromolecules 34:9193–9196CrossRef

Yang S, Li L, Cholli AL, Kumar J, Tripathy SK (2003) Azobenzene-modified poly(l-glutamic acid) (AZOPLGA): its conformational and photodynamic properties†. Biomacromolecules 4:366–371CrossRef

Zheng PJ, Hu X, Zhao XY, Tam KC, Gan LH (2004) Photoregulated sol-gel transition of novel azobenzene functionalized hydroxypropyl methylcellulose and its alpha-cyclodextrin complexes. Macromol Rapid Commun 25:678–682CrossRef

Titel: Synthesis and characterization of azobenzene hydroxypropyl cellulose with photochromic and thermotropic liquid crystal properties
verfasst von: Wang Qin
Zhijun Li
Jixiang Li
Lihua Zhang
Ruilai Liu
Haiqing Liu
Publikationsdatum: 01.02.2015
Verlag: Springer Netherlands
Erschienen in: Cellulose / Ausgabe 1/2015
Print ISSN: 0969-0239
Elektronische ISSN: 1572-882X
DOI: https://doi.org/10.1007/s10570-014-0479-9

Springer Professional

Abstract

Bitte loggen Sie sich ein, um Zugang zu Ihrer Lizenz zu erhalten.

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

Springer Professional "Technik"

Springer Professional "Wirtschaft+Technik"

Weitere Artikel der Ausgabe 1/2015

Formation of liquid crystals and behavior of LCST upon addition of xanthan gum (XG) to hydroxypropyl cellulose (HPC) solutions

Bacterial cellulose-titanium dioxide nanocomposites: nanostructural characteristics, antibacterial mechanism, and biocompatibility

Population balance based modeling of changes in cellulose molecular weight distribution during ageing

Porous cellulose facilitated by ionic liquid [BMIM]Cl: fabrication, characterization, and modification

Dissolution of cellulose from different sources in an NaOH/urea aqueous system at low temperature

Cellulose levulinate: a protecting group for cellulose that can be selectively removed in the presence of other ester groups