Thermally Stable Fluorescent Maleimide/Isobutene Alternating Copolymers Containing Pyrenyl and Alkynylpyrenyl Moieties in the Side Chain

Abstract

Alternating copolymers of maleimides containing pyrenyl and alkynylpyrenyl moieties with isobutene (IB) were synthesized as a new class of heat‐resistant and fluorescent polymers. N‐(1‐Pyrenyl)maleimide (1) and N‐[4‐(1‐pyrenylethynyl)phenyl]maleimide (2) were copolymerized with IB in the presence and absence of N‐methylmaleimide (3). The obtained maleimide/IB copolymers showed excellent thermal stability and high glass transition temperatures, and were soluble in common organic solvents. The copolymers including the alkynylpyrenyl fluorophore emitted strong fluorescence with a high quantum efficiency (Φ = 0.83) even in the presence of air and upon heating. Solid‐state fluorescence in transparent films was also investigated.magnified image

Thermosetting Maleimide/Isobutene Alternating Copolymer as a New Class of Transparent Materials

“…This result supports the fact that the copolymer is equivalently composed of the AMI and IB repeating units. The characteristic peaks observed in this study were similar to those for the alternating copolymers obtained by the copolymerization of various RMIs and IB 18–25. In the spectrum shown in Figure 1, no peak was detected for the unreacted maleimide residue, although it is expected to be observed at 6.72 ppm if the allyl group of the AMI monomer is incorporated into the copolymerization.…”

“…In the present study, we synthesized an alternating copolymer of N ‐allylmaleimide (AMI) and IB [poly(AMI‐ alt ‐IB)] as a new class of thermosetting polymers with excellent transparency by a radical copolymerization process. Doi et al and we have already reported various kinds of alternating copolymers of N ‐alkylmaleimides (RMI) with isobutene (IB) [poly(RMI‐ alt ‐IB)s] having excellent thermal stabilities, as well as excellent mechanical and optical properties 18–25. The poly(AMI‐ alt ‐IB) obtained in the present study includes an unsaturated group in the N ‐substituent, which is curable upon heating (Scheme ).…”

PEGylated Fluorescent Nanoparticles from One-Pot Atom Transfer Radical Polymerization and “Click Chemistry”

“…The copolymerization of a strongly-electron-accepting with an electron-donating monomer produces an alternate copolymer [37,38]. N-substituted maleimide (electron-accepting monomer) and styrene (electron-donating monomer) comprise an extensively-studied system [39,40].…”

A Pyrene- and Phosphonate-Containing Fluorescent Probe as Guest Molecule in a Host Polymer Matrix

“…NPyrMal is a weak luminescent probe due to the presence of a conjugated system ( i.e. , maleimide motif) which partially absorbs light and strongly decreases the pyrene motif fluorescence [ 57 , 58 , 59 , 60 , 61 , 62 ].…”