Direct organocatalytic thioglycolic acid esterification of cellulose nanocrystals: A simple entry to click chemistry on the surface of nanocellulose

•Novel and simple thia-group functionalization of cellulose nanocrystals.•Versatile functionalization of cellulose nanocrystal and nanocellulose.•Biomimetic cellulose nanocrystal and nanocellulose based reducing agents.•Selective introduction of fluorescent and UV active molecules on cellulose nanoc...

Full description

Saved in:
Bibliographic Details
Published in:Carbohydrate polymer technologies and applications 2022-06, Vol.3, p.100205, Article 100205
Main Authors: Alimohammadzadeh, Rana, Rafi, Abdolrahim A., Goclik, Lisa, Tai, Cheuk-Wai, Cordova, Armando
Format: Article
Language:English
Subjects:
Cellulose nanocrystals
Click chemistry
Direct esterification
Heterogeneous catalysis
Organocatalysis
Thiol-functionalized nanocellulose
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:•Novel and simple thia-group functionalization of cellulose nanocrystals.•Versatile functionalization of cellulose nanocrystal and nanocellulose.•Biomimetic cellulose nanocrystal and nanocellulose based reducing agents.•Selective introduction of fluorescent and UV active molecules on cellulose nanocrystals.•Autocatalytic surface modification of cellulose nanocrystals. The mild and simple direct organocatalytic esterification of cellulose nanocrystals (CNC) and nanocellulose-based materials (e.g. foams and films) with thioglycolic acid (TGA) is disclosed. The transformation gives the corresponding thiol group (-SH) functionalized crystalline nanocellulose (CNC-SH) using simple, naturally occurring, and non-toxic organic acids (e.g. tartaric acid) as catalysts. We also discovered that the direct esterification of cellulose with TGA is autocatalytic (i.e. the TGA is catalyzing its own esterification). The introduction of the -SH functionality at the nanocellulose surface opens up for further selective applications. This was demonstrated by attaching organic catalysts and fluorescent molecules, which are useful as sensors, to the CNC-SH surface by thiol-ene click chemistry. Another application is to use the CNC-SH-based foam as a heterogeneous biomimetic reducing agent, which is stable during multiple recycles, for the copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition (“click” reaction). [Display omitted]
ISSN:2666-8939
2666-8939
DOI:10.1016/j.carpta.2022.100205