TY - JOUR
T1 - Fluorescent imino and secondary amino chitosans as potential sensing biomaterials
AU - Jatunov, Sorel
AU - Franconetti, Antonio
AU - Prado-Gotor, Rafael
AU - Heras, Angeles
AU - Mengíbar, Marian
AU - Cabrera-Escribano, Francisca
N1 - Publisher Copyright:
© 2015 Elsevier Ltd. All rights reserved.
PY - 2015/6/5
Y1 - 2015/6/5
N2 - A variety of fluorescent imino and secondary amino chitosans were synthesized under very mild conditions by reaction of the biopolymer amino functions with aromatic aldehydes in an acidified methanolic suspension. Simultaneous reactions of several aldehydes with chitosan were successfully carried out, and kinetic studies showed that 1-pyrenecarboxaldehyde reacts the fastest among them. An unprecedented study on the evaluation of the degree of N-substitution (DS, ranging from 31.7% to 12.0%) for the chitosan Schiff bases by using solid state CPMAS 13C NMR is performed. A linear correlation between the DS obtained for the secondary amino chitosans by 1H NMR (55.3-10.2%) and those obtained by CPMAS 13C NMR (34.4-13.8%) has allowed us to calculate an empirical correlation factor that could be applied on chitosan-based aromatic systems. The new chiral-labelled chitosan derivatives exhibit a stable fluorescent behaviour, which was used to explore solvent sensoring applications.
AB - A variety of fluorescent imino and secondary amino chitosans were synthesized under very mild conditions by reaction of the biopolymer amino functions with aromatic aldehydes in an acidified methanolic suspension. Simultaneous reactions of several aldehydes with chitosan were successfully carried out, and kinetic studies showed that 1-pyrenecarboxaldehyde reacts the fastest among them. An unprecedented study on the evaluation of the degree of N-substitution (DS, ranging from 31.7% to 12.0%) for the chitosan Schiff bases by using solid state CPMAS 13C NMR is performed. A linear correlation between the DS obtained for the secondary amino chitosans by 1H NMR (55.3-10.2%) and those obtained by CPMAS 13C NMR (34.4-13.8%) has allowed us to calculate an empirical correlation factor that could be applied on chitosan-based aromatic systems. The new chiral-labelled chitosan derivatives exhibit a stable fluorescent behaviour, which was used to explore solvent sensoring applications.
KW - Chemical
KW - Chitosan Schiff Bases
KW - Fluorescence
KW - Secondary Amino Chitosans
KW - Sensing biomaterials
KW - Solid state NMR
UR - https://www.scopus.com/pages/publications/84923165706
U2 - 10.1016/j.carbpol.2015.01.061
DO - 10.1016/j.carbpol.2015.01.061
M3 - Article
C2 - 25843861
AN - SCOPUS:84923165706
SN - 0144-8617
VL - 123
SP - 288
EP - 296
JO - Carbohydrate Polymers
JF - Carbohydrate Polymers
ER -