Synthesis and optical properties of new polyurethane cationomers with anchored stilbene chromophores

Abstract

An ionic diol bearing a one-sided urethane-stilbene group located on the ammonium quaternary structure was prepared and proposed as an intermediate for polyurethane ionomer synthesis. Polyurethane cationomers with stilbene ionic groups based on poly(tetramethylene oxide) diols, 4,4Ј-diphenylmethane diisocyanate and the aforementioned ionic diol, were synthesized and characterized. Some aspects of the trans-cis photoisomerism and fluorescent emission of the stilbene chromophore in polyurethane cationomers were studied comparatively with the urethane-stilbene diol. The stilbene polycations absorbed at A ϭ 316 nm and emitted violet-blue light with an emission maxima at F ϭ 444 nm (dimethylformamide solution) and F ϭ 465 nm (film). These polymers are known for their elastomeric properties and are assumed to be of great interest for some future applications.

Synthesis and characterization of film-forming poly(urethaneimide) cationomers containing quaternary ammonium groups

“…This repulsion effect can be strongly reduced or even suppressed by adding an electrolyte like LiBr which is capable of screening the cationic charges. If the electrolyte concentration is high enough, a normal viscometry behavior can even be obtained for polyurethane cationomers in polar organic solvents [15,30]. with methyl tosylate.…”

Synthesis and properties of polyurethane cationomers with urethane-cholesteryl and dodecylmethylammonium moieties

“…Moreover, is expected that by incorporating a chain extender with a didodecyl side chain on the quaternary ammonium structure, the overall properties to combine characteristics of the conventional polyurethanes [17] with those derived from existence of ionic groups dominated by a long hydrocarbon chain, offering polymers suitable for specialized coatings. For example, in our previous works [18 -28] we proved that the traditional properties of some polyurethane ionomers can be diversified by the introduction of specific functional groups, such as peptides [18], dihydroxamic acids [19,20], pyridinium [21] or those of stilbene [22], azoaromatic [23 -25], triazene [26,27], quinone type [28] in order to obtain new bio(photo)materials with a large spectrum of applications. Also, we are interested in ionic polyurethanes containing poly(ethylene glycol) segments into their structure, since it has been frequently used as co-monomer in preparing biodegradable polymers due to its biocompatibility and biodegradability [29].…”

Effect of microstructural arrangement of MDI‐based polyurethanes on their photoproperties

“…A pendent fluorophore can be attached covalently or electrostatically to a polyurethane molecule . For example, chromophores have been introduced as a pendent group during the quaternization of polyurethanes to study their film and solution properties. In addition, nitrobenzene has been used as a quencher in polyurethane systems that contain pyrene as a pendent group bound to the backbone of the polymer .…”

“…These polymers can be used as metal ion sensors since they show metal‐ion‐sensitive fluorescence quenching . Some aspects of cis–trans photoisomerization and fluorescent emission of stilbene chromophores in polyurethane cationomers have been studied . An aqueous polyurethane emulsion that contains the fluorescent moiety 1,4‐diamino‐2,3‐diphenoxyanthraquinone (DDAQ) has been incorporated into a polyurethane chain made using 2,4‐tolylene diisocyanate (TDI), poly(propylene glycol), and 2,2‐dimethylol propionic acid.…”