Synthesis, isolation, characterization, and properties of small‐size aromatic macrocycles for poly(arylene ether ketone)s

Fabrication of Aromatic‐Aliphatic Aminoketone Polymers with Terminal Fluorine Groups

“…Altogether, the disturbing moieties are covalently incorporated in the PAK chains and cycles (see Supporting Information). Therefore we concluded that use of the common base such as K 2 CO 3 , [24,45] , which is established as a suitable catalyst for nucleophilic aromatic substitution of DFB to produce PEK, PES, and related polymers, [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34] is not suitable to produce molecularly well defined PAK. MALDI TOF measurements of the crude PAK also revealed defects in the polymer chain when solvents such as dimethyl sulfoxide (DMSO), N-cyclohexyl-2-pyrrolidone, and sulfolane, respectively, are used for the syntheses.…”

“…[9] Oligomeric or polymeric building blocks for the target molecules should be readily available via the nucleophilic aromatic substitution reaction [9][10][11][12][13][14][15] of secondary aliphatic diamines with 4,4 0 -difluorobenzophenone (DFB). This simple method would be in analogy to the well-established syntheses of poly(ether ketone)s (PEK) [16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33] or poly(ether sulfone)s (PES) [34][35][36][37][38] , both based on DFB (Scheme 1). Surprisingly, no reports on the target PAK were available in spite of the fact that related synthetic routes are known, e.g., to produce N-substituted Michler's Ketone derivatives.…”

LB Film Structure of Nanometer-Scale PEEKK Macrocyclic Oligomers

“…The cyclic oligo(ether ether ketone ketone) (PEEKKC) was synthesized by a so-called pseudo-high-dilution technique [6] and the product was recrystallized twice from a tetrahydrofuran (THF)/acetone mixture (1 : 1000). The purity was examined using NMR and FT-IR techniques.…”

“…In recent studies, we prepared a series of diameter-controllable nanometer-scale RCOs [4] that have stable nanometer-scale cavities due to their rigid chain structures and amphiphilic properties that come from hydrophilic oxygen atoms and hydrophobic groups. The cavity itself may have special interesting properties when the RCO molecules are assembled into two-dimensional ordered films.…”

Synthesis, structure and ring-opening polymerization of phenolphthalein macrocyclic polyarylates

“…An alternative route to produce phenolphthalein polyarylates is through ring-opening polymerization of macrocyclic precursors. The advantages of using cyclic oligomers such as carbonates, [12] aryl esters, [13][14][15][16][17][18][19] ethers, [20][21][22][23][24][25][26][27][28][29][30][31][32] amides, [33][34] and sulfides [35][36] as precursors of high-performance thermoplastics have been widely recognized. The cyclic oligomers offer a unique combination of low melt viscosity and the possibility of undergoing controlled polymerization in the melt without the liberation of volatile byproducts.…”