Synthesis of photoactive single‐chain folded polymeric nanoparticles via combination of radical polymerization techniques and Menschutkin click chemistry

Abstract

This contribution reports that synthesis of polystyrene based photoactive polymeric nanoparticles by radical copolymerization and Menschutkin Chemistry methodology. In the first step, poly(styrene-co-chloromethyl styrene) was achieved by thermally initiated radical copolymerizations and subsequently copolymers were reacted to commercially available Type II photoiniator (Michler's ketone) in dilute condition in order to achieve intramolecular crosslinked polymeric nanoparticles. After the characterization studies, polymeric nanoparticles were used for free radical photopolymerization of methacrylic formulations to determine the initiation efficiency. Upon UV irradiation, resulting polymeric nanoparticle lost its globular structure by releasing benzophenone part and transformed into linear copolymer analogue.

Preparation of Single Chain Nanoparticles via Photoinduced Double Collapse Process

“…Unlike various nanoparticles, folding chains are soluble due to the intramolecular crosslinking nature. Mainly, varying folding architectures have been designed such as photoresponsive compounds, metal complexes, size and surface tunable nanoparticles, thermoresponsive hydrogels, and stable polymeric nanoparticles under sonication . Linear copolymers can undergo chemical interactions either by their pendant units or external crosslinkers to achieve intramolecularly crosslinked polymeric nanoparticles.…”

“…Unlike various nanoparticles, folding chains are soluble due to the intramolecular crosslinking nature. Mainly, varying folding architectures have been designed such as photoresponsive compounds, [4,5] metal complexes, [6,7] size and surface tun-to photoactive benzophenone and azide moieties subsequently. After that, corresponding functional polymer was used for the synthesis of single chain nanoparticles by double collapse strategy which includes combination of photoinduced azide crosslinking and radical coupling processes (Scheme 2).…”

“…[12] Linear copolymers can undergo chemical interactions either by their pendant units or external crosslinkers to achieve intramolecularly crosslinked polymeric nanoparticles. To gain single chain nanoparticles, varying synthetic methods have been carried out such as Menschutkin quaternization chemistry, [5,13,14] stepwise folding, [15] Diels-Alder click, [16,17] benzocyclobutene-coupling chemistry, [18] click cyclo-addition, [19][20][21] photocrosslinking, [22][23][24][25] and host-guest interactions. [26] These intramolecularly crosslinked nanoparticles have found various applications in gas capturing, [27] controlled release, [28] and nanocomposites.…”

Synthesis and characterization of POSS hybrid organogels using Menschutkin quaternization chemistry

“…So far Menschutkin chemistry has been applied to obtain various functional organic compounds using tertiary amines and alkyl halides . The corresponding chemical reaction converts tertiary amines to quaternary salts and the resultant compound may become hydrophilic depending on the chemical structures of the reactants.…”

Study of Diels–Alder reactions between furan and maleimide model compounds and the preparation of a healable thermo‐reversible polyurethane

“…INTRODUCTION Since the inception of the "click" chemistry concept, 1 a wide range of synthetic fields of chemical and polymer science has made use of the versatility of click chemistry for efficiently constructing linkages for structural modifications as well as preparation of novel polymeric materials. [2][3][4][5] In addition to many irreversible well-known click reactions such as copper catalyzed azide-alkyne cycloaddition and thiol-ene addition, 1,6-8 the thermo-reversible Diels-Alder (DA) reaction has emerged prominently contributing to the broad click repertoire. [9][10][11][12] The growing impact of the DA chemistry on the synthesis of remendable, thermally reversible, and recyclable materials has stimulated studies to gain more insight in the reaction pathway and kinetics, [13][14][15][16][17][18][19][20][21][22][23][24][25][26] which has been the starting point of this research.…”