Coloring–decoloring behavior of fluoroalkyl end‐capped 2‐acrylamido‐2‐methylpropanesulfonic acid oligomer/acetone composite in methanol

Abstract

A reddish‐brown fluoroalkyl end‐capped 2‐acrylamido‐2‐methylpropanesulfonic acid (AMPS) oligomer/acetone composite was prepared by heating the white oligomer powder with acetone at 80 °C for 3 h. The color was not observed in the corresponding non‐fluorinated AMPS oligomer/acetone composite, which was prepared under similar conditions. The coloring was probably caused by the formation of acetone polyaldol condensation products in the fluorinated oligomeric gel network cores. The colored RF‐(AMPS)n‐RF/acetone composite powders were stable and did not exhibit any color change after 2 years in natural light at room temperature. The colored composite powders dissolved in methanol to give a reddish‐brown solution at room temperature. However, the retro‐polyaldol condensation decolored the solution after 1 day at room temperature. This is the first example of the retro‐aldol polycondensation of acetone under mild conditions. The decoloration increased by between 38‐ and 70‐fold under UV irradiation, compared with that in dark conditions. The coloring–decoloring behavior was consistent and repeatable; therefore our fluorinated oligomer/acetone composites are promising candidates for new fluorinated coloring materials. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 2555–2564

Homoaldol condensation of aromatic ketones in fluoroalkyl end-capped 2-acrylamido-2-methylpropanesulfonic acid oligomeric gel network cores

“…[37] In addition, the retro-polyaldol condensation of acetone was also found to decolor the solution after 1 day at room temperature. [37] Here, we report that R F -(AMPS) n -R F oligomer can interact with not only acetone but also aromatic ketones such as 4′-methoxyacetophenone (MAP) to give the homoaldol condensation product under mild conditions, although the corresponding non-fluorinated AMPS oligomer and sulfuric acid cannot afford the corresponding product at all under similar conditions. EXPERIMENTAL Measurements 1 H NMR spectra were recorded using a JEOL JNM-ECA 500 (500 MHz) FT NMR SYSTEM (Tokyo, Japan).…”

“…Therefore, it is particularly desirable to develop fluoroalkyl end‐capped AMPS oligomeric nanoparticles for encapsulating not only metal nanoparticles but also organic guest molecules. In fact, we have very recently succeeded in the encapsulation of acetone in fluoroalkyl end‐capped AMPS oligomeric aggregate cores to give the reddish‐brown fluorinated AMPS oligomer [R F ‐(AMPS) n ‐R F ]/acetone composite . It has been demonstrated that the color can arise from acetone encapsulated in the fluorinated AMPS oligomeric gel network cores forming acetone polyaldol condensation products .…”

“…In fact, we have very recently succeeded in the encapsulation of acetone in fluoroalkyl end‐capped AMPS oligomeric aggregate cores to give the reddish‐brown fluorinated AMPS oligomer [R F ‐(AMPS) n ‐R F ]/acetone composite . It has been demonstrated that the color can arise from acetone encapsulated in the fluorinated AMPS oligomeric gel network cores forming acetone polyaldol condensation products . In addition, the retro‐polyaldol condensation of acetone was also found to decolor the solution after 1 day at room temperature .…”

“…[37] It has been demonstrated that the color can arise from acetone encapsulated in the fluorinated AMPS oligomeric gel network cores forming acetone polyaldol condensation products. [37] In addition, the retro-polyaldol condensation of acetone was also found to decolor the solution after 1 day at room temperature. [37] Here, we report that R F -(AMPS) n -R F oligomer can interact with not only acetone but also aromatic ketones such as 4′-methoxyacetophenone (MAP) to give the homoaldol condensation product under mild conditions, although the corresponding non-fluorinated AMPS oligomer and sulfuric acid cannot afford the corresponding product at all under similar conditions.…”

Color-changing behavior of fluoroalkyl end-capped 2-methacryloyloxyethanesulfonic acid oligomer/polyaniline nanocomposites, triggered by a variety of basic compounds

“…We have hitherto comprehensively studied on the preparation and applications of fluoroalkylated polymers, especially, ABA triblock-type fluoroalkyl end-capped oligomers [R F -(M) n -R F : R F = fluoroalkyl groups, M=radical polymerizable monomer], and these fluorinated oligomers can exhibit a wide variety of unique properties such as high solubility, surface-active property, and nanometer size-controlled molecular aggregates, which cannot be achieved by the corresponding non-fluorinated and randomly fluoroalkylated ones [33][34][35][36][37]. The self-assembled fluorinated oligomeric aggregates formed by these fluoroalkyl end-capped oligomers can provide suitable host moieties to interact with numerous guest molecules such as fullerene, carbon nanotubes, gold, silver and copper nanoparticles, and organic dyes, affording the corresponding fluorinated aggregates/guest molecules nanocomposites [38][39][40][41][42][43][44][45][46][47]. In addition, preparation of poly(vinylidene fluoride) copolymers/silica nanocomposites has been reported including their unique properties [48][49][50].…”