“Click”-Capture, Ring-Opening Metathesis Polymerization (ROMP), Release: Facile Triazolation Utilizing ROMP-Derived Oligomeric Phosphates

Abstract

Soluble, high-load ROMP-derived oligomeric triazole phosphates (OTP) are reported for application as efficient triazolating reagents of nucleophilic species. Utilizing a “Click”-capture, ROMP, release protocol, the efficient and purification free, direct triazolation of N-, O- and S-nucleophilic species was successfully achieved. A variety of OTP derivatives were rapidly synthesized as free-flowing solids on multi-gram scale from commercially available materials.

A general approach for construction of asymmetric modification membranes for gated flow nanochannels

“…In this paper, we experimentally demonstrate a new and general method for asymmetrical modication within the nanochannels of an anodic aluminum oxide (AAO) membrane. [16][17][18] Atom transfer radical polymerization (ATRP), 19 ring-opening metathesis polymerization (ROMP), 20 and the selfpolymerization of dopamine (DOP-SP) methods 14 were adopted for asymmetrically graing a series of functional polymer brushes, including hydrophilic poly(3-sulfopropyl methacrylate potassium salt) (PSPMA) and poly(2-(methacryloyloxy)ethylmethylammonium chloride) (PMETAC), poly(hydrophobic pentadecauorooctyl-5-norbornene-2-carboxylate) (PNCA-F 15 ), double responsive poly(N-isopropylacrylamide) (PNIPAM, temperature-responsive polymer brushes) and poly-((dimethylamino)ethyl methacrylate) (PDMAEMA, pH-responsive polymer brushes), in addition to bioactive polydopamine, onto the inner walls of the AAO nanochannels by half-cell reactions in a sandwich-type reactor. Moreover, the Au and Pd nanoparticle catalysts were also asymmetrically modied within the nanochannels of the AAO membrane based on the double hydrophilic PSPMA@PMETAC followed by ion exchange and reduction reaction, showing good ow-through catalysis and permeability properties.…”

Water-soluble polyphosphonate-based bottlebrush copolymers via aqueous ring-opening metathesis polymerization

“…Other phosphoester-based norbornene oligomers have been synthesized via ROMP and used as either benzylating 48 or triazolating reagents. 49 Concerns about PEG as a non-biodegradable polyether, which can accumulate in the body and lead to the formation of antiPEG-antibodies, [50][51][52] have motivated the search for other bottlebrush type materials for biomedical applications derived from other functional hydrophilic polymers as PEG alternatives, e.g. norbornene-based polyoxazolines 53 or N-carboxyanhydrides, 54,55 but the application of ROMP of such macromonomers is neither under biorelevant conditions nor are the side chains prone to degrade.…”

Triazolization of Enolizable Ketones with Primary Amines: A General Strategy toward Multifunctional 1,2,3‐Triazoles

“… [43] The reaction starts from readily available enolizable ketones 1 , primary alkylamines 2 and 4‐nitrophenyl azide 3 (4‐NPA), and was named ‘the triazolization reaction of ketones’. The term triazolization, however, should not be confused with triazolyzation, [44] triazolylation [34] or triazolation, [38,45] which have been used elsewhere in the literature. The triazolization reaction affords 1‐alkyl‐1,2,3‐triazoles and is therefore complementary to the earlier described azide‐ketone cycloaddition reactions, as the scope of the latter is mostly limited to triazoles with aryl substituents at the N1‐position.…”