Details

Autor(en) / Beteiligte

• Brown, Chanelle J.
• Gandour, Richard D.
• Turner, S. Richard

Titel

Unsymmetrically Substituted Stilbene–Maleic‐Anhydride Copolymers: Improving Synthesis and Measuring Substituent Effects on Conversion

Ist Teil von

• Macromolecular chemistry and physics, 2023-01, Vol.224 (1), p.n/a

Ort / Verlag

Weinheim: Wiley Subscription Services, Inc

Erscheinungsjahr

2023

Quelle

Wiley-Blackwell Journals

Beschreibungen/Notizen

• Syntheses of certain substituted‐stilbene–maleic anhydride, precisely alternating copolymers have a long history of challenges that include gelation and long polymerization times. This work reports the use of anisole as a polymerization solvent that prevents gelation during the copolymerization. Several substituted (E)‐stilbenes (2‐methyl, 3‐methyl, 4‐methyl, 4‐tert‐butyl, 2‐methoxy, 4‐methoxy, 4‐methoxycarbonyl, 4‐trifluoromethyl, 2,4′‐dimethyl, and 3,4′‐dimethyl) are copolymerized with maleic anhydride without gelation; however, copolymerization of 4,4′‐dimethylstilbene gelled, presumably because of symmetry. Substituents affect the rates of conversion. In general, after 30 min, donors copolymerize with maleic anhydride faster; acceptors, slower. 2‐Methyl and 2,4′‐dimethyl are slower, presumably due to sterics. At longer times, conversions of 4‐tert‐butyl and 4‐methoxy are significantly reduced. Substituted‐stilbene−maleic anhydride copolymers are highly desired for applications in membrane protein extraction. However, the copolymerization of substituted‐stilbenes with maleic anhydride often results in the formation of gels. These hetero‐phase copolymerizations are barriers to controlling molecular weight and dispersities. Herein we describe several approaches that hinder gelation: anisole as a polymerization solvent and the use of non‐symmetrical substituted‐stilbene monomers.