Color Indicator for Supramolecular Polymer Chemistry: Phenolphthalein‐Containing Thermo‐ and pH‐Sensitive N‐(Isopropyl)acrylamide Copolymers and β‐Cyclodextrin Complexation

Abstract

The copolymerization parameters of N-(isopropyl)acrylamide (1) and N-(2-hydroxy-5-(1-(4-hydroxyphenyl)-3-oxo-1,3-dihydroisobenzofuran-1-yl)benzyl)acrylamide (2) are determined. For both monomers, the homoaddition proceeds slightly faster than the heteroaddition step; however, the polymer formation occurs in a statistic fashion. Copolymers of different compositions are prepared and the cloud points are determined. Thereby, a significant influence of the concentration of monomer 2 and the pH value is found. For the first time, the complexation of polymer attached phenolphthalein by β-cyclodextrins is shown. Furthermore, it is possible to achieve a decomplexation by the addition of suitable guest molecules. Both procedures can be followed with the naked eye.

Computer‐aided drug design to explore cyclodextrin therapeutics and biomedical applications

“…Due to the discrepancy in cavity size, each CD has its own ability to form inclusion complexes with specific guests, an ability which depends on the size-selective complexation between the guest molecule and the hydrophobic CD cavity. [28][29][30][31] The diameter of the hydrophobic part of the guest has to be smaller than the minimum diameter to permit the formation of a stable axial inclusion complex. NMR studies [32] have demonstrated that α-CD is conformationally flexible in aqueous solution.…”

Polymers and Dyes: Developments and Applications

“…As another example of polymerizable triphenylmethane dyes, a radically polymerizable phenolphthalein derivative was obtained through reaction of phenolphthalein with N-(hydroxymethyl)acrylamide [57][58][59]. The latter compound possesses a relatively high reactivity towards nucleophilic attacks, which enables condensation with electron-rich aromatic substances under Friedel-Crafts-like conditions.…”

Direct access to functional (Meth)acrylate copolymers through transesterification with lithium alkoxides

“…For example, by employing copolymerization, researchers have been able to fine tune mechanical, thermal, or optical properties . In fact, even small amounts of suitable comonomers can significantly influence certain properties, for example, the material's impact resistance or crystallinity . In this context, a prominent example is the incorporation of small amounts of isophthalic acid into poly(ethylene terephthalate) which lowers the material's crystallinity and increases its transparency …”