A Metathesis Route for BODIPY Labeled Polyolefins

Abstract

It is demonstrated how acyclic diene metathesis polymerization (ADMET) provides an efficient strategy for the labeling of polyolefins. The versatility of phosphorus chemistry allows designing substituted BODIPY monomers or chain stoppers for the synthesis of precise labeled (degradable) polyphosphoesters.

Poly(alkylidene chlorophosphate)s via Acyclic Diene Metathesis Polymerization: A General Platform for the Postpolymerization Modification of Poly(phosphoester)s

“…31−33 The versatile monomer synthesis starts from POCl 3 that is esterified sequentially with the alcohols of choice. 34 Two unsaturated alcohols are necessary to introduce the polymerizable units, while the third pendant ester is free to introduce functional groups. Herein, in contrast to previous works, we chose to leave the pendant group a phosphoric acid chloride in order to generate highly electrophilic PPEs that can readily react with various nucleophiles.…”

Poly(phosphonate)-mediated Horner–Wadsworth–Emmons reactions

“…27,28,[35][36][37][38] Tailoring these properties allowed us to enhance the HWE reaction and its workup procedure in several model reactions. 27,28,[35][36][37][38] Tailoring these properties allowed us to enhance the HWE reaction and its workup procedure in several model reactions.…”

“…27,28,35,36,38 With this report we introduce this material into the organic-chemical science and give chemists and researchers an adjustable and versatile tool to improve their synthesis in the lab and industry. In addition, this is the first report on the synthesis of linear poly (hydroxyalkylene phosphate)s from poly(alkylalkylene phosphonate)s. In our current and past work on this versatile class of materials we have demonstrated the usability of poly( phosphonate)s in materials science and the biomedical field.…”

Reactive poly(phosphoester)-telechelics

“…We recently introduced metathesis polymerization to novel PPE structures that further increase the functional group tolerance during their production. [10][11][12] We are interested in the chemistry of poly(phosphoester)s (PPEs) since the versatile phosphorus chemistry allows for the generation of highly functional, biorelated, and -degradable materials. [9] Herein, we further increase the versatility of PPEs prepared by acyclic diene metathesis (ADMET) polymerization by copolymerization of phosphate monomers with several reactive chain termination agents to produce perfect linear PPE telechelics with various functional end-groups.…”