Dye-functionalized polymers via ring opening metathesis polymerization: principal routes and applications

Abstract

Herein, highlights from the recent literature regarding functional dye-polymer conjugates obtained by ring opening metathesis polymerization (ROMP) are presented and the different approaches to incorporate dyes during the initiation, propagation, and termination step in ROMP are discussed. Applications in the field of chemical sensors, bioimaging, electroactive materials, self-assembly, photochromic and photoreactive materials are used to illustrate the versatility of ROMP as a technique to prepare complex functional materials. Graphical abstract

Fluorescent ROMP Monomers and Copolymers for Biomedical Applications

“…[20,[24][25][26] For ring-opening metathesis polymerization (ROMP), this has recently been summarized and illustrated. [27,28] In the context of visualization of polymers and polymeric materials in biological environments, each of these approaches has different advantages and disadvantages. Fluorescent initiators can be quite convenient if the initiator reacts quantitatively, and if there are no chain transfer reactions (which is true for living polymerizations like anionic polymerization and ROMP).…”

“…6), respectively. [17,27,28,33] were removed by vacuum and a dark solid was obtained. A filter-column (CH 2 Cl 2 :ethyl acetate 1:1) gave the NBD-labeled monomer M1 (yield: 342.5 mg, 0.92 mmol, 41%).…”

“…Additionally, the fluorophore can be introduced by postpolymerization functionalization . For ring‐opening metathesis polymerization (ROMP), this has recently been summarized and illustrated . In the context of visualization of polymers and polymeric materials in biological environments, each of these approaches has different advantages and disadvantages.…”

“…ROMP monomers labeled with fluorescent coumarin ( 1 ), DABCYL ( 2 ), fluorescein ( 3 ), EDANS ( 4 ), anthracene ( 5 ) and rhodamin B ( 6 ), respectively …”

Synthesis and characterization of naphthalimide-functionalized polynorbornenes

“…Thus, a number of dye-functionalized polymers have been successfully obtained [25, 26], while the living nature of ROMP allowed the precise placement of dye molecules in dedicated segments of block copolymers and combining them with stimuli-responsive comonomers [27]. This renders ROMP the method of choice for the synthesis of naphthalimide-functionalized polymers which is the objective of this work.…”