Degradable fluorescent single-chain nanoparticles based on metathesis polymers

Abstract

We introduce the facile synthesis of fluorescent single-chain nanoparticles (SCNPs) based on chain-shattering acyclic diene metathesis (ADMET) polymers featuring self-immolative azobenzene motifs. An electrophilic alkoxyetherification is utilized to introduce the photoreactive moieties required for the subsequent chain collapse via UV-induced nitrile imine-mediated tetrazole-ene cycloaddition (NITEC).

Hybrid polymers bearing oligo-l-lysine(carboxybenzyl)s: synthesis and investigations of secondary structure

“…Our synthetic strategy is based on a combination of ring opening polymerization (ROP) of N-carboxyanhydride (NCA), followed by ADMET polymerization of appropriately bis-enefunctionalized oligomers to place the folding-elements of Lys n s along a polymer chain, subsequently studying their intraand interchain secondary structures. Acyclic diene metathesis (ADMET) polymerization [32][33][34] opens up possibilities to introduce different kinds of functional groups [35][36][37][38] into a polyethylene chain, introducing even anti-inammatory drugs, such as ibuprofen and naproxen, into a polyethylene backbone. 39 The ROP of NCA monomers is a viable and proven strategy to obtain articial homo-and block co-peptides, where end group functionalized polymers can be obtained, given that the ROP mechanism follows the aspects of "livingness".…”

Soft Matter Technology at KIT: Chemical Perspective from Nanoarchitectures to Microstructures

“…Concomitantly, the NITEC reaction has also been successfully employed in polymer ligation, [18] protein and peptide functionalization, [19] to trigger photoswitchable wettability, [20] redox and radical sensor formation, [21] self-reporting fluorescent polymers, [22] the preparation of degradable fluorescent single-chain [23] nanoparticles and networks. [24] Specifically, the latter aimed for the adoption of a fluorescence-based methodology enabling the quantification of ligation points in photochemically prepared polymer networks.…”

Oligo(thioether‐ester)s Blocks in Polyurethanes for Slowly Releasing Active Payloads

“…The molecular weight of the polymers was found to decrease upon UV irradiation or thermal treatment due to the cleavage of the azo bonds. Degradable polymers containing azobenzene units in their main chains were also prepared by electrophilic alkoxyetherification . Finally, depolymerizations induced by intramolecular cyclization were reported such as the conversion of 2‐mercaptoethanol derivatives to thiocarbonates triggered by reduction, or esters with γ‐amine or γ‐thiol to thiolactones and lactams .…”