Photoresponsive Cellulose Nanocrystals
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 carboxyli...
Saved in:
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Wiley
2011-07-01
|
| Series: | Nanomaterials and Nanotechnology |
| Subjects: | |
| Online Access: | http://www.intechopen.com/journals/nanomaterials_and_nanotechnology/photoresponsive_cellulose_nanocrystals |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1832547922449793024 |
|---|---|
| author | Dimitris S Argyropoulos Hasan Sadeghifar Ilari Filpponen |
| author_facet | Dimitris S Argyropoulos Hasan Sadeghifar Ilari Filpponen |
| author_sort | Dimitris S Argyropoulos |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-6ac1ae8295b6401bb0ee5c758701920b |
| institution | Kabale University |
| issn | 1847-9804 |
| language | English |
| publishDate | 2011-07-01 |
| publisher | Wiley |
| record_format | Article |
| series | Nanomaterials and Nanotechnology |
| spelling | doaj-art-6ac1ae8295b6401bb0ee5c758701920b2025-02-03T06:42:54ZengWileyNanomaterials and Nanotechnology1847-98042011-07-0111http://dx.doi.org/10.5772/50949Photoresponsive Cellulose NanocrystalsDimitris S ArgyropoulosHasan SadeghifarIlari FilpponenIn 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.http://www.intechopen.com/journals/nanomaterials_and_nanotechnology/photoresponsive_cellulose_nanocrystals celluloseclick chemistryfluorescencephotodimerization |
| spellingShingle | Dimitris S Argyropoulos Hasan Sadeghifar Ilari Filpponen Photoresponsive Cellulose Nanocrystals Nanomaterials and Nanotechnology cellulose click chemistry fluorescence photodimerization |
| title | Photoresponsive Cellulose Nanocrystals |
| title_full | Photoresponsive Cellulose Nanocrystals |
| title_fullStr | Photoresponsive Cellulose Nanocrystals |
| title_full_unstemmed | Photoresponsive Cellulose Nanocrystals |
| title_short | Photoresponsive Cellulose Nanocrystals |
| title_sort | photoresponsive cellulose nanocrystals |
| topic | cellulose click chemistry fluorescence photodimerization |
| url | http://www.intechopen.com/journals/nanomaterials_and_nanotechnology/photoresponsive_cellulose_nanocrystals |
| work_keys_str_mv | AT dimitrissargyropoulos photoresponsivecellulosenanocrystals AT hasansadeghifar photoresponsivecellulosenanocrystals AT ilarifilpponen photoresponsivecellulosenanocrystals |