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 organization: | 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 |
Peer reviewed: | Yes |
Rights: | cc_by |
Usage restriction: | openAccess |
Self-archived version: | publishedVersion |
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