Photoresponsive Cellulose Nanocrystals Regular Paper

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http://hdl.handle.net/10138/178765

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Filpponen , I , Sadeghifar , H & Argyropoulos , D S 2011 , ' Photoresponsive Cellulose Nanocrystals Regular Paper ' , Nanomaterials and nanotechnology , vol. 1 , no. 1 , pp. 34-43 .

Title: Photoresponsive Cellulose Nanocrystals Regular Paper
Author: Filpponen, Ilari; Sadeghifar, Hasan; Argyropoulos, Dimitris S.
Contributor: University of Helsinki, Aalto University
University of Helsinki, Department of Chemistry
Date: 2011
Language: eng
Number of pages: 10
Belongs to series: Nanomaterials and nanotechnology
ISSN: 1847-9804
URI: http://hdl.handle.net/10138/178765
Abstract: In this communication a method for the creation of fluorescent cellulose nanoparticles using click chemistry and subsequent photodimerization of the installed side-chains is demonstrated. In the first step, the primary hydroxyl groups on the surface of the CNCs were converted to carboxylic acids by using TEMPO-mediated hypohalite oxidation. The alkyne groups, essential for the click reaction, were introduced into the surface of TEMPO-oxidized CNCs via carbodiimide-mediated formation of an amide linkage between monomers carrying an amine functionality and carboxylic acid groups on the surface of the TEMPO-oxidized CNCs. Finally, the reaction of surface-modified TEMPO-oxidized cellulose nanocrystals and azido-bearing coumarin and anthracene monomers were carried out by means of a click chemistry, i.e., Copper(I))-catalyzed Azide-Alkyne Cycloaddition (CuAAC) to produce highly photo-responsive and fluorescent cellulose nanoparticles. Most significantly, the installed coumarin and/or anthracene side-chains were shown to undergo UV-induced [2+2] and [4+4] cycloaddition reactions, bringing and locking the cellulose nanocrystals together. This effort paves the way towards creating, cellulosic photo responsive nano-arrays with the potential of photo reversibility since these reactions are known to be reversible at varying wavelengths.
Subject: cellulose
click chemistry
fluorescence
photodimerization
116 Chemical sciences
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