A novel poly(arylene ether sulfone) (PAES) with pinacol phenylboronate pendants (PAES-B) was prepared by the borylation of brominated PAES (PAES-Br). The reaction was carried out under mild conditions in the presence of cuprous iodide and tri-n-butylphosphine in tetrahydrofuran solution. After heat treatment at 150°C for 132 h, the PAES-B exhibited an interesting solvent resistance. Fourier transform infrared spectroscopy (FTIR) and thermal analysis were performed to investigate the reason. FTIR spectra showed that heat treatment could facilitate losing of pinacol groups and formation of phenylboronic acid in the polymer. Meanwhile, differential scanning calorimetric (DSC) curves demonstrated that the polymer had cross-linking behaviors during heat treatment. In addition, the thermal oxidative stability of PAES-B was researched by the thermogravimetric analysis (TGA).
JäkleF. Borylated polyolefins and their applications. J Inorg Organomet P2005; 15: 293–307.
2.
JäkleF. Advances in the synthesis of organoborane polymers for optical, electronic, and sensory applications. Chem Rev2010; 110: 3985–4022.
3.
ColquhounHMLewisDFDanielsJAHerbertsonPLMacBrideJr, AHStephensonIR. Polyetherketones from diarylcarboranes: a new approach to semi-inorganic polymers. Polymer1997; 38: 2447–2453.
4.
GaoJGLiuYFWangFL. Structure and properties of boron-containing bisphenol-A formaldehyde resin. Eur Polym J2001; 37: 207–210.
NagaiAMurakamiTNagataYKokadoKChujoY. Synthesis and photostability of poly(p-phenylenevinylene-borane)s. Macromolecules2009; 42: 7217–7220.
7.
WongKTChienYYLiaoYLLinCCChouMYLeungMK. Efficient and convenient nonaqueous workup procedure for the preparation of arylboronic esters. J Org Chem2002; 67: 1041–1044.
8.
IshiyamaTIshidaKMiyauraN. Synthesis of pinacol arylboronates via cross-coupling reaction of bis(pinacolato)diboron with chloroarenes catalyzed by palladium(0)–tricyclohexylphosphine complexes. Tetrahedron2001; 57: 9813–9816.
9.
ZhuWMaD. Formation of arylboronates by a CuI-catalyzed coupling reaction of pinacolborane with aryl iodides at room temperature. Org Lett2006; 8: 261–263.
10.
KleebergCDangLLinZYMarderTB. A facile route to aryl boronates: room-temperature, copper-catalyzed borylation of aryl halides with alkoxy diboron reagents. Angew Chem Int Ed2009; 48: 5350–5354.
11.
KishiHShiYBHuangJYeeAF. Shear ductility and toughenability study of highly cross-linked epoxy/polyethersulphone. J Mater Sci1997; 32: 761–771.
12.
FriedmanMWalshG. High performance films: Review of new materials and trends. Polym Eng Sci2002; 42: 1756–1788.
13.
WangYShiBLLiXC. Effects of coagulation bath temperature on performances of polyethersulfone membranes modified by nanosilver particles in situ reduction. Polym Eng Sci2013; 53: 1614–1622.
14.
AbateLBlancoICicalaGReccaGScamporrinoA. The influence of chain -ends on the thermal and rheological properties of some 40/60 PES/PEES copolymers. Polym Eng Sci2009; 49: 1477–1483.
15.
ChengFJäkleF. Boron-containing polymers as versatile building blocks for functional nanostructured materials. Polym Chem2011; 2: 2122–2132.
16.
ChangYLeeHHKimSHJoTSBaeC. Scope and regioselectivity of Iridium-catalyzed C−H borylation of aromatic main-chain polymers. Macromolecules2013; 46: 1754–1764.
17.
LiuBJRobertsonGPGuiverMDShiZQNavessinTHoldcroftS. Fluorinated poly(aryl ether) containing a 4-bromophenyl pendant group and its phosphonated derivative. Macromol Rapid Commun2006; 27: 1411–1413.
18.
WangYPYueXGPangJHLiXFLiNZhangHB. Synthesis and properties of poly(aryl ether sulfones) functionalized with pendant perfluoroalkyl sulfonic acid for proton exchange membrane. Chem J Chin Univ2012; 33: 1100–1105.
19.
ZoltewiczJASaleAA. Cleavage of pyridyl methyl ethers and reactions of 3-halopyridines with sodium methoxide. J Org Chem1970; 36: 3462–3467.
20.
MorganABJursJLTourJM. Synthesis, flame-retardancy testing, and preliminary mechanism studies of nonhalogenated aromatic boronic acids: a new class of condensed-phase polymer flame-retardant additives for acrylonitrile –butadiene–styrene and polycarbonate. J Appl Polym Sci2000; 76: 1257–1259.
21.
MartínCRondaJCCádizV. Boron-containing novolac resins as flame retardant materials. Polym Degrad and Stabil2006; 91: 747–754.
