Research Article
New 1,2,3-Triazole Containing Polyesters via Click Step-Growth
Polymerization and Nanoparticles Made of Them
Tengiz Kantaria , Temur Kantaria, Giorgi Titvinidze , Giuli Otinashvili ,
Nino Kupatadze , Nino Zavradashvili , David Tugushi, and Ramaz Katsarava
Institute of Chemistry and Molecular Engineering, Agricultural University of Georgia, Kakha Bendukidze University Campus,
No. 240 David Agmashenebeli Alley, Tbilisi, Georgia
Correspondence should be addressed to Ramaz Katsarava; r.katsarava@agruni.edu.ge
Received 22 November 2017; Accepted 6 February 2018; Published 27 March 2018
Academic Editor: Xuan Zhou
Copyright © 2018 Tengiz Kantaria et al. his is an open access article distributed under the Creative Commons Attribution License,
which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
High-molecular-weight AA-BB-type aliphatic polyesters were synthesized via Cu(I)-catalyzed click step-growth polymerization
(SGP) following a new synthetic strategy. he synthesis was performed between diyne and diazide monomers in an organic solvent
as one pot process using three components and two stages. he dipropargyl esters of dicarboxylic acids (component 1) were used as
diyne monomers, di-(bromoacetic acid)-alkylene diesters (component 2) were used as precursors of diazide monomers, and sodium
azide (component 3) was used for generating diazide monomers. he SGP was carried out in two steps: at Step 1 dibromoacetates
interacted with two moles of sodium azide resulting in diazide monomers which interacted in situ with diyne monomers at
Step 2 in the presence of Cu(I) catalyst. A systematic study was done for optimizing the multiparameter click SGP in terms of the
solvent, duration of both Step 1 and Step 2, solution concentration, catalyst concentration, catalyst and catalyst activator (ligand)
nature, catalyst/ligand mole ratio, and temperature of both steps of the click SGP. As a result, high-molecular-weight (
푊
up to
74 kDa) elastic ilm-forming click polyesters were obtained. he new polymers were found suitable for fabricating biodegradable
nanoparticles, which are promising as drug delivery containers in nanotherapy.
1. Introduction
Copper(I) catalyzed and copper-free azide-alkyne cycloaddi-
tions (CuAAC and CuFAAC) are one of the most widely used
click reactions. CuAAC click reaction has been extensively
used in biochemistry and biotechnology [1], in polymer
chemistry for dendrimer synthesis/functionalization, surface
immobilization/modiication, orthogonally functionalizing
polymers, and its integration with ATRP (atom transfer radi-
cal polymerization) and ROP (ring-opening polymerization)
for synthesizing block-copolymers, cyclic polymers, hyper-
branched macromolecules, star-shaped polymers, and cross-
linked polymeric networks [2–11]. CuAAC reaction was also
widely employed in orthogonal multiple click reactions for
constructing various well-deined complex macromolecular
structures [12, 13].
he azide-alkyne click polymerization appears as a pow-
erful tool for the synthesis of polymers with versatile archi-
tectures by step-growth polymerization (SGP). Due to the
high reaction rates and quantitative yields, high-molecular-
weights can be achieved. It is important to note that CuAAC
click reaction results in the formation of 1,2,3-triazole ring
which is known as low toxic moiety [14, 15]. Furthermore,
triazole rings-containing compounds display a broad spec-
trum of biological activities, including antimicrobial, antivi-
ral, antifungal, anticancer, anti-inlammatory, antitubercular,
antioxidant, analgesic, and antimalarial activities [16, 17].
1,2,3-Triazoles are highly promising for the designing of var-
ious functional coatings such as anticorrosive, antimicrobial,
self-healing, and hybrid nanocomposite [18].
here are rather limited publications on the application
of CuAAC in SGP for constructing either AB or AA-BB
type polymeric backbones: D´ ıaz et al. reported about the
synthesis of new adhesive polymers with N-arylsulfonamide
moieties in the backbones [19]; Van Steenis et al. obtained
novel conjugated aromatic polymers with molecular weights
(MWs) of 60–396 kDa (
푊
) by click SGP indicating
that this reaction is suitable for constructing long-chain
Hindawi
International Journal of Polymer Science
Volume 2018, Article ID 6798258, 14 pages
https://doi.org/10.1155/2018/6798258