Simultaneous Orthogonal Chemoligations on Multiresponsive Microgels

Abstract

We describe the straightforward synthesis of "clickable" multiresponsive microgels containing both carboxylic acid groups and azidohydrin or terminal alkyne groups, via a one-pot multistage polymerization approach. The clickable functional groups on the microgels were confirmed by FTIR. Additionally, we simultaneously performed "click" and acid-amine coupling reactions on microgels with fluorescent dyes containing complementary functional groups. Epifluorescence microscopy was employed to confirm the coupling of those dyes to the microgels. The orthogonality of the click reaction to other functional groups such as hydroxyl, carboxylic acid, and amino groups was confirmed, suggesting the potential utility of such microgels in applications where multifunctional colloidal particles are required.

Porous polymer particles—A comprehensive guide to synthesis, characterization, functionalization and applications

“…Although there are numerous studies on CuAAC functionalization of nonporous polymers [280,298,328,[336][337][338][339][340][341][342][343][344][345][346][347][348][349][350][351], silica [352][353][354] and metal particles [355], the amount of publications on porous polymer particles is limited. Finn et al [356] described the click functionalization of a commercial porous agarose resin for affinity chromatography.…”

Synthesis and physicochemical properties of cationic microgels based on poly(N-isopropylmethacrylamide)

“…In many of these applications, the introduction of specific chemical functionalities is desired, such that the polymer can be elaborated upon following synthesis. Toward that end, functionalities such as carboxyl [11], azido [12] and glycidyl [13] groups have been copolymerized into pNIPAm microgels. However, the primary amine, a reactive group that is particularly useful for bioconjugation [14], has been far less studied in microgel synthesis.…”

Water-soluble starlike poly(acrylic acid) graft polymer: preparation and application as templates for silver nanoclusters

“…1) that the strong absorption peak at 2,112 cm -1 assigned to stretched vibration of -N 3 [46] and the strong absorption peaks at 3,300 and 2,129 cm -1 assigned to stretched vibration of -C:CH, respectively, are disappeared in the infrared spectra of PAA m -g-PAA n . A new absorption at about 1,600-1,640 cm -1 typical of the triazole ring appeared [46], which seemed not to be obvious because of its incorporation with strong absorption peak of the carbonyl group. In addition, the star polymers showed the distinct stretching bands at 3,432 cm -1 (-OH) and 1,712 cm -1 (C=O) for the arms, and the strong absorption at 2,977 and 2,863 cm -1 for the initiators.…”

“…When isopropanol was employed as a replacement of the mixture of THF/H 2 O, however, click coupling of the alkynyl and azide groups was complete 72 h. It can be seen from the infrared spectra of P(t-BA) n -N 3 , PPA m , and PAA m -g-PAA n (Fig. 1) that the strong absorption peak at 2,112 cm -1 assigned to stretched vibration of -N 3 [46] and the strong absorption peaks at 3,300 and 2,129 cm -1 assigned to stretched vibration of -C:CH, respectively, are disappeared in the infrared spectra of PAA m -g-PAA n . A new absorption at about 1,600-1,640 cm -1 typical of the triazole ring appeared [46], which seemed not to be obvious because of its incorporation with strong absorption peak of the carbonyl group.…”