Alternative o-Quinodimethane Cross-Linking Precursors for Intramolecular Chain Collapse Nanoparticles

Advances in Click Chemistry for Single-Chain Nanoparticle Construction

“…I agree with the suggested changes, that can be made easily by the editorial office. [7,22,28,29], poly(styrene) [3,22,23,[30][31][32], poly(haloalkyl styrene) [3,33], poly(4-N-Boc-vinylaniline) [33], poly(sodium 4-styrenesulfonate) [22], poly(N-alkyl acrylamide) [22,34,35] Atom transfer radical polymerization ATRP Poly(alkyl methacrylates) [14], poly(alkyl acrylates) [11,12], poly(styrene) [36], poly(N-hydroxyethyl acrylamide) [37] Nitroxide mediated radical polymerization NMP Poly(alkyl methacrylates) [9,[38][39][40], poly(alkyl acrylates) [40], poly(styrene) [2,38,40], poly(haloalkyl styrene) [40], poly(fluorene) [41] Ring opening metathesis polymerization ROMP Poly(-caprolactone) [38], poly(carbonates) [42] poly(norbornenes) [13,43,44] * For SCNP copolymer and terpolymer precursors, only the nature of the main component is indicated.…”

“…Covalent bonding interactions Vinyl [33,38,39,42] Radical coupling & Cross-Metathesis Benzocyclobutene [40,53] Diels-Alder reaction * Benzosulfone [9,28,41] Diels-Alder reaction * Azide + Protected alkyne [3,10,21,22,30,34] Copper-catalyzed [3+2] cycloaddition ** Carboxilic acid [54] Amide formation Isocyanate [23] Urea formation ** Enediyne [11,12,24,29] Bergman & Photo-Bergman cyclization Sulfonyl azide [31] Nitrene-mediated cross-linking Benzoxazine [36] Ring opening polymerization Alkyne [25] Glaser-Hay coupling * * C-C click chemistry. ** N-C click chemistry.…”

Intramolecular Cross-linking of Polymers Using Difunctional Acetylenes via Click Chemistry

“…Recently, several strategies were employed for the preparation of polymeric nanoparticles, including intramolecular cross-linking of single polymer chains containing cross-linkable groups in ultra-diluted reaction conditions [11][12][13][14][15][16][17] and single-chain collapse of macromolecules containing suitable reactive groups along the chain with bifunctional cross-linkers [18,19].…”

Metal-Free Polymethyl Methacrylate (PMMA) Nanoparticles by Enamine “Click” Chemistry at Room Temperature

“…Significant efforts have been devoted in recent years to open new routes to unimolecular nanoparticles relying on efficient synthetic methods for the controlled, irreversible intramolecular collapse of individual polymer chains. In this sense, different synthetic approaches have been reported: free-radical cross-linking of vinyl units [6][7][8], thermal cross-linking of benzocyclobutene and o-quinodimethane functional groups by Diels-Alder reactions [9,10], copper-catalyzed azide-alkyne "click" chemistry [11][12][13] and fast cross-linking of isocyanate groups from appropriate precursor chains by diamines [14].…”

“…PS-nanoparticles were also synthesized by Croce et al [10] following this route from PS-precursors containing o-quinodimethane cross-linking units instead of BCB moieties. A clear limitation of the technique is that reaction conditions are harsh, precluding the use of thermally labile polymers and/or functional groups.…”