Synthesis and characterization of novel optically active poly(ester‐imide)s with high Tg and good thermal stability

A series of novel optically active poly(ester‐imide)s (ter‐PEIs) with high glass transition temperature (T_g), good thermal stability, and solubility were successfully designed and synthesized by direct polycondensation reactions, using p‐hydroxybenzoic acid (PHB), 4,4’‐dihydroxybenzophenone, and a chiral diacid, N,N'‐(pyromellitoyl)‐bis‐L‐phenylalanine diacid as monomers. The resulting terpolymers were characterized by¹H‐NMR, FTIR, element analysis, thermogravimetric analysis, different scanning calorimeter and wide‐angle x‐ray diffraction, etc. The ter‐PEIs are amorphous polymers with good heat resistance and high T_gs. They are soluble in many common polar organic solvents and show optically rotation property. The specific rotation values of the ter‐PEIs increase with the molar ratio of the chiral diacid, and the rigid PHB monomer is beneficial to increase the T_gs of the polymers. Copyright © 2013 John Wiley & Sons, Ltd.     

Synthesis and characterization of optically active poly(amide-imide)s based on [N,N′-(4,4′-carbonyldiphtaloyl)-bis-lamino diacid]s and 1,5-bis(4-aminophenyl)penta-1,4-dien-3-one

Six dicarboxylic acids 3a-3f were synthesized by the reaction of 3,3’,4,4’-benzophenonetetracarboxylic dianhydride 1 with L-aminoacids 2a-2f in a solution of glacial acetic acid/pyridine(Py) at refluxing temperature.Then six new poly(amide-imide)s PAIs were synthesized from the direct polycondensation reaction of[N,N’-(4,4’- carbonyldiphtaloyl)-bis-L-amino diacid]s with 1,5-bis(4-aminophenyl)penta-1,4-dien-3-one(APPD).The polymerization reactions produced a series of new optically active PAIs with high yield and good inherent viscosity.Also these PAIs are optically active and soluble in various organic solvents.These resulting new polymers can be used in column chromatography for the separation of enantiomeric mixtures.The resulted polymers were fully characterized by means of FTIR and ~1H-NMR spectroscopy,elemental analyses,inherent viscosity measurements,solubility tests and thermogravimetric analysis(TGA).     

Optically active poly(amide–imide)s containing axially dissymmetric 1,1′-binaphthyl moieties

Novel optically active aromatic poly(amide–imide)s (PAIs) were prepared from newly synthesized 2,2′-bis(3,4-dicarboxybenzamido)-1,1′-binaphthyl dianhydride ((+ )-, (S)-, and (R)-BNDADA). PAIs based on dianhydride monomers with different ee % were investigated with respect to their structures and chiroptical properties. These polymers were highly soluble in polar aprotic solvents such as N,N-dimethylacetamide, N-methyl-2-pyrrolidone, pyridine, etc., and showed high glass transition temperatures of 287–290°C and 5% weight loss temperatures of 450–465°C in nitrogen. Optically active PAIs exhibited high specific rotations, excellent optical stabilities, and a dependence of optical activities on temperature. Investigations on chiroptical properties indicated that chiral conformation was possessed by optically active PAIs. © 1999 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 37: 3147–3154, 1999     

Diisocyanate route as a convenient method for the preparation of novel optically active poly(amide-imide)s based on N-trimellitylimido-S-valine

A new class of optically active poly(amide-imide)s based on an α-amino acid was synthesized via direct polycondensation reaction of different diisocyanates with a chiral diacid monomer. The step-growth polymerization reactions of N-trimellitylimido-S-valine (TISV) (1) with 4,4′-methylene-bis(4-phenylisocyanate) (MDI) (2) was performed under microwave irradiation, as well as solution polymerization under graduate heating and reflux conditions. The optimized polymerization conditions for each method were performed with tolylene-2,4-diisocyanate (TDI) (3), hexamethylene diisocyanate (HDI) (4), and isophorone diisocyanate (IPDI) (5) to produce optically active poly(amide-imide)s via diisocyanate route. The resulting polymers have inherent viscosities in the range of 0.02-1.10 dL/g. Decomposition temperatures for 5% weight loss (T₅) occurred above 300 °C (by TGA) in nitrogen atmospheres. These polymers are optically active, thermally stable and soluble in amide-type solvents. Some structural characterization and physical properties of this new optically active poly(amide-imide)s are reported.     

Synthesis and characterization of optically active and organosoluble poly(amide-imide)s containing imidazole rings as pendent groups by direct polycondensation

Six new optically active poly(amide-imide)s(PAIs) 6a-f were prepared by direct polycondensation reaction of N-trimelli-tylimido-L-histidine 4 as a chiral diacid with various aromatic diamines 5a-f.Triphenyl phosphite(TPP)/pyridine(Py) in the presence of calcium chloride(CaCl2) and N-methyl-2-pyrrolidone(NMP) were successfully applied to direct polycondensation reaction.The resulting new polymers were in good yields,and had inherent viscosities ranging between 0.29 and 0.41 dL g-1 and were detected with elem...     

Synthesis and properties of poly(imide-sulfonate)s

Polycondensations of N,N′-bis(hydroxyalkyl)pyromellitic diimides, N,N′-bis(hydroxyphenyl)-pyromellitic diimides, N,N′-bis(hydroxyalkyl)-3,3′,4,4′-benzophenonetetracarboxylic diimides and N,N′-bis(hydroxyphenyl)-3,3′-4,4′-benzophenonetetracarboxylic diimides with aromatic disulfonyl chlorides were carried out in pyridine to produce poly(imide-sulfonate)s. The resulting polymers had inherent viscosities in the range of 0.25–0.38 dL/g. These poly(imide-sulfonate)s were insoluble in common organic solvents and had relatively good thermal stability. The TGA data showed 10% weight losses at 253–365°C and residual weights at 500°C were 22–72% in nitrogen.     

Synthesis and properties of poly(arylene ether phenyl-s-triazine)s

A series of new poly(arylene ether phenyl-s-triazine)s was prepared by the nucleophilic aromatic substitution polymerization of the potassium salt of bisphenols with 2,4-bis (halophenyl)-6-phenyl-s-triazine in N-methyl-2-pyrrolidone at elevated temperature. The polymers with inherent viscosities exceeding 0.5 were obtained after polymerization for 1 h using 2,4-bis(fluorophenyl)-6-phenyl-s-triazine as a monomer. The glass transition temperatures of the resulting polymers ranged from 200 to 260°C depending on the bisphenol used in the polymer synthesis. The poly(arylene ether phenyl-s-triazine)s demonstrated excellent thermal stabilities in excess of 490°C (5% weight loss in air). The isothermal TGA measurements (400°C under air or nitrogen atmosphere) revealed that the 4,4'-biphenol- and hydroquinone-based poly(arylene ether phenyl-s-triazine)s belong to the most superior class of heat resistant polymers, such as polyimide Kapton?. The mechanical properties of these polymers are also described. © 1994 John Wiley & Sons, Inc.     

Microwave-promoted synthesis of new optically active poly(ester-imide)s derived from N,N-(pyromellitoyl)-bis-l-leucine diacid chloride and aromatic diols

Pyromellitic dianhydride (benzene-1,2,4,5-tetracarboxylic dianhydride) (1) was reacted with l-leucine (2) in a mixture of acetic acid and pyridine (3:2) and the resulting imide-acid [N,N^′-(pyromellitoyl)-bis-l-leucine diacid] (4) was obtained in quantitative yield. The compound (4) was converted to the N,N^′-(pyromellitoyl)-bis-l-leucine diacid chloride (5) by reaction with thionyl chloride. A new facile and rapid polycondensation reaction of this diacid chloride (5) with several aromatic diols such as phenol phthalein (6a), bisphenol-A (6b), 4,4^′-hydroquinone (6c), 1,8-dihydroxyanthraquinone (6d), 1,5-dihydroxy naphthalene (6e), 4,4-dihydroxy biphenyl (6f), and 2,4-dihydroxyacetophenone (6g) was developed by using a domestic microwave oven in the presence of a small amount of a polar organic medium such as o-cresol. The polymerization reactions proceeded rapidly and are completed within 10 min, producing a series of optically active poly(ester-imide)s (PEIs) with good yield and moderate inherent viscosity of 0.10-0.27 dl/g. All of the above polymers were fully characterized by IR, elemental analyses and specific rotation. Some structural characterization and physical properties of these optically active PEIs are reported.     

Preparation and characterization of optically active and organosoluble poly(amide‐imide)s from polycondensation reaction of N,N′‐(4,4′‐sulphonediphthaloyl)‐bis‐L‐isoleucine diacid with aromatic diamines

3,3′,4,4′‐Diphenylsulfonetetracarboxylic dianhydride (1) was reacted with L ‐isoleucine (2) in acetic acid and the resulting imide‐acid (3) was obtained in high yield. The diacid chloride (4) was prepared from the diacid derivative (3) by reaction with thionyl chloride. The polycondensation reaction of diacid chloride (4) with several aromatic diamines such as 4,4′‐sulfonyldianiline (5a), 4,4′‐diaminodiphenyl methane (5b), 4,4′‐diaminodiphenylether (5c), p‐phenylenediamine (5d),m‐phenylenediamine (5e), 2,4‐diaminotoluene (5f) and 4,4′‐diaminobiphenyl (5g) was performed by two conventional methods: low temperature solution polycondensation and short period reflux conditions. In order to compare conventional solution polycondensation reaction methods with microwave‐assisted polycondensation, the reactions were also carried out under microwave conditions with a small amount of o‐cresol that acts as a primary microwave absorber. The reaction mixture was irradiated for 6 min with 100% of radiation power. Several new optically active poly(amide‐imide)s with inherent viscosity ranging from 0.23 to 0.41 dl/g were obtained with high yield. All of the earlier polymers were fully characterized by IR, elemental analyses and specific rotation techniques. Some structural characterizations and physical properties of these new optically active poly(amide‐imide)s are reported. Copyright © 2005 John Wiley & Sons, Ltd.     

Studies on synthesis and in vitro biodegradability of novel optically active nanostructure poly(ester-imide)s containing <Emphasis Type="SmallCaps">l</Emphasis>-phenylalanine and <Emphasis Type="SmallCaps">l</Emphasis>-isoleucine linkages

A series of biodegradable functional amino-acid-based poly(ester-imide)s (PEI)s were designed and synthesized by the direct polycondensation reaction of chiral diacids composed of naturally occurring α-amino acids with 4,4′-thiobis(2-tert-butyl-5-methylphenol) in the presence of tosyl chloride, pyridine, and N,N-dimethylformamide as a condensing agent. These new chiral polymers were characterized with respect to chemical structure and purity using specific rotation experiments, FT-IR, ¹H-NMR, techniques, and elemental analysis. The surface morphology of these polymers was investigated by field emission scanning electron microscopy. The result indicated nanoscale morphology of the obtained polymers. Thermal stability and the weight loss behavior of the resulting PEIs were studied by TGA techniques. All PEIs showed no significant weight loss below 400 °C in a N₂ environment. The monomers and prepared polymers were co-cultivated with airborne fungal spores in culture media to study their biological activity. Soil burial test was also used for evaluation of their biodegradation behavior. The results showed that the synthesized monomers and their derived polymers are biologically active and that their degradation products are probably nontoxic to microbial growth.     

Synthesis and characterization of optically active poly(amide-imide)s containing photosensitive chalcone units in the main chain

<正>A series of new optically active poly(amide-imide)s were synthesized by direct polycondensation reaction of 4,4'-diaminochalcone with several N-trimellitylimido-L-amino acids using a tosyl chloride(TsCl),pyridine(Py) and dimethylformamide(DMF) system as condensing agent.The resulting thermally stable poly(amide-imide)s were obtained in good to high yields and inherent viscosities ranging between 0.35 dL/g and 0.58 dL/g and were characterized with FTIR, ~1H-NMR,CHN,Ultraviolet,TGA and DTG techniques.     

Microwave‐assisted synthesis of optically active poly(amide imide)s derived from diacid chloride containing epiclon and L‐leucine with aromatic diamines

Epiclon [3a,4,5,7a‐tetrahydro‐7‐methyl‐5‐(tetrahydro‐2,5‐dioxo‐3‐furanyl)‐1,3‐isobenzofurandione or 5‐(2,5‐dioxotetrahydrofurfuryl)‐3‐methyl‐3‐cyclohexyl‐1,2‐dicarboxylic acid anhydride] was reacted with L ‐leucine in acetic acid, and the resulting imide acid ( 3 ) was obtained in a high yield. The diacid chloride ( 4 ) was obtained from its diacid derivative 3 by a reaction with oxalyl chloride in dry carbon tetrachloride. The polycondensation reaction of 4 with several aromatic diamines, such as 4,4′‐sulfonyldianiline, 4,4′‐diaminodiphenylmethane, 4,4′‐diaminodiphenylether, p‐phenylenediamine, m‐phenylenediamine, 2,4‐diaminotoluene, and 1,5‐diaminonaphthalene, was developed with a domestic microwave oven in the presence of a small amount of a polar organic medium such as N‐methylpyrrolidone. The polymerization reactions were also performed with two other methods: low‐temperature solution polycondensation in the presence of trimethylsilyl chloride and reflux conditions. A series of optically active poly(amide imide)s with moderate yields and inherent viscosities of 0.12–0.19 dL/g were obtained. All of these polymers were fully characterized by IR, elemental analysis, and specific rotation techniques. Some structural characterizations and physical properties of these optically active poly(amide imide)s are reported. © 2003 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 41: 1077–1090, 2003     

Synthesis and properties of novel soluble poly(amide‐imide)s with different pendant substituents

Two types of novel fluorinated diimide‐diacid monomers—[2,2′‐(4,4′‐(3′‐methylbiphenyl‐2,5‐diyl)bis(oxy)bis(3‐(trifluoromethyl)‐4,1‐phenylene))bis(1,3‐dioxoisoindoline‐5‐carboxylic acid)] (III) and [2,2′‐(4,4′‐(3′‐(trifluoromethyl)biphenyl‐2,5‐diyl)bis(oxy)bis(3‐(trifluoromethyl)‐4,1‐phenylene))bis(1,3‐dioxoisoindoline‐5‐carboxylic acid)] (IV)—were respectively designed and prepared by the condensation of diamines I and II with two molar equivalents of trimellitic anhydride. From both diimide‐diacids, two series of novel poly(amide‐imide)s (PAIs) (IIIa–IIIe and IVa–IVe) bearing different pendant groups were prepared by direct polymerization with various aromatic diamines (a–e). All the PAIs had a high glass transition temperatures (T_gs, 232–265 °C), excellent thermal stability (exhibiting only 5% weight loss at 493–542 °C under nitrogen) and good solubility in various organic solvents due to the introduction of the bulky pendant groups. The cast films of these PAIs (80–90 μm) had good optical transparency (73–81% at 450 nm, 85–88% at 550 nm and 87–89% at 800 nm) and low dielectric constants (2.65–2.98 at 1 MHz). The spin‐coated films of these PAIs presented a minimum birefringence value as low as 0.0077–0.0143 at 650 nm and low optical absorption at the near‐infrared optical communication wavelengths of 1310 and 1550 nm. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017 , 55, 3243–3252     

Synthesis and properties of aromatic poly (ether sulfone)s and poly (ether ketone)s based on methyl-substituted biphenyl-4,4′-diols

Novel methyl-substituted aromatic poly (ether sulfone)s and poly (ether ketone)s were synthesized from combinations of 3,3′,5,5′-tetramethylbipheny-4,4′-diol and 2,2′,3,3′,5,5′-hexamethylbiphenyl-4,4′-diol, and 4,4′-dichlorodiphenyl sulfone and 4,4′-difluorobenzo-phenone by nucleophilic aromatic substitution polycondensation. The polycondensations proceeded quantitatively in a N-methyl-2-pyrrolidone-toluene solvent system in the presence of anhydrous potassium carbonate to afford the polymers with inherent viscosities between 0.86 and 1.55 dL/g. The methyl-substituted poly (ether sulfone)s and poly (ether ketone)s showed good solubility in common organic solvents such as chloroform, tetrahydrofuran, pyridine, m-cresol, and N,N-dimethylacetamide. The tetramethyl- and hexamethyl-substituted aromatic polyethers had higher glass transition temperatures than the corresponding unsubstituted polymers, and did not decompose below 350°C in both air and nitrogen atmospheres. The films of the methyl-substituted poly (ether ketone)s became insoluble in chloroform by the irradiation of ultraviolet light, indicating the occurrence of photochemical crosslinking reactions. © 1994 John Wiley & Sons, Inc.     

Synthesis of optically active poly(amide‐imide)s derived from N,N′‐(4,4′‐carbonyldiphthaloyl)‐bis‐L‐leucine diacid chloride and aromatic diamines by microwave radiation

3,3′,4,4′‐benzophenonetetracarboxylic dianhydride (4,4′‐carbonyldiphathalic anhydride) was reacted with L ‐leucine in a mixture of acetic acid and pyridine (3 : 2), and the resulting imide‐acid [N,N′‐(4,4′‐carbonyldiphthaloyl)‐bis‐L ‐leucine diacid] was obtained in quantitative yield. The compound was converted to the N,N′‐(4,4′‐carbonyldiphthaloyl)‐bis‐L ‐leucine diacid chloride by reaction with thionyl chloride. A new facile and rapid polycondensation reaction of this diacid chloride with several aromatic diamines such as 4,4′‐diaminodiphenyl methane, 2,4‐diaminotoluene, 4,4′‐sulfonyldianiline, p‐phenylenedi‐amine, 4,4′‐diaminodiphenylether, and m‐phenylenediamine was developed by using a domestic microwave oven in the presence of a small amount of a polar organic medium such as O‐cresol. The polymerization reactions proceeded rapidly compared with the conventional solution polycondensation and were completed within 6 min, producing a series of optically active poly(amide‐imide)s with a high yield and an inherent viscosity of 0.37–0.57 dL/g. All of the above polymers were fully characterized by IR, elemental analyses, and specific rotation. Some structural characterization and physical properties of these optically active poly(amide‐imide)s are reported. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 39: 177–186, 2001     

Novel thermally stable and chiral poly(amide-imide)s bearing from N,N′-(4,4′-diphthaloyl)-bis-l-isoleucine diacid: Synthesis and characterization

Novel optically active aromatic poly(amide-imide)s (PAIs) were prepared from newly synthesized N,N′-(4,4′-diphthaloyl)-bis-l-isoleucine diacid (3) via polycondensation with various diamines. The diacid was synthesized by the condensation reaction of 3,3′,4,4′-biphenyltetracarboxylic dianhydride (1) with l-isoleucine (2) in a mixture of acetic acid and pyridine (3:2 v/v). All the polymers were obtained in quantitative yields with inherent viscosities of 0.20-0.43 dL g⁻¹. All the polymers were highly organosoluble in solvents like N-methyl-2-pyrrolidinone (NMP), N,N-dimethylacetamide (DMAc), N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), tetrahydrofuran, γ-butyrolactone, cyclohexanone and chloroform at room temperature or upon heating. These poly(amide-imide)s had glass transition temperatures between 198 and 231 °C, and their 10% weight-loss temperatures were ranging from 368 to 398 °C and 353 to 375 °C under nitrogen and air, respectively. The polyimide films had tensile strengths in the range of 63-88 MPa and tensile moduli in the range of 0.8-1.4 GPa. These poly(amide-imide)s possessed chiral properties and the specific rotations were in the range of −3.10° to −72.92°.     

Synthesis and characterization of new type soluble poly(amide–imide)s based on 6FDA imide modified polyterephthalamides

A series of new poly(amide–imide)s (PAIs, series III ) with good processability and characteristics was synthesized by utilizing organosoluble polyimide (PI, 6FDA–PI series) to improve poor‐solubility polyamide (PA, PTPA series), which used terephthalic acid (TPA) as a monomer. The III series PAIs were synthesized starting from the 2 : 1 molar ratio of aromatic diamines ( I ) and 6FDA to prepare imide ring‐preformed diamines ( II ) and then reacted with equimolar amount of TPA by direct polycondensation. Furthermore, by adjustment of the stoichiometry of the I , II, and TPA monomers, PAIs IV having various components were prepared. Most of the resulting PAIs having inherent viscosities between 0.70 and 1.74 dL/g were obtained in quantitative yields, and they were readily soluble in polar solvents such as N,N‐dimethylacetamide, N‐methyl‐2‐pyrrolidone, dimethylformamide, and dimethyl sulfoxide. All of the soluble PAIs afforded transparent, flexible, and tough films. The glass‐transition temperatures of PAIs III were in the range of 236–256 °C, and the 10% weight loss temperatures were recorded at 522–553 °C in nitrogen. The char yields of the III series polymers in nitrogen atmosphere were all higher than 56% even at 800 °C. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 39: 93–104, 2001     

Synthesis and properties of carbamate‐ and amine‐containing poly(phenylacetylenes)

The 3‐ and 4‐aminophenylacetylenes protected by t‐butoxycarbonyl (t‐Boc) and 9‐fluorenylmethoxycarbonyl (Fmoc) groups ( 3a – 6a ) were synthesized and polymerized using [(nbd)RhCl]₂ ( 1 ) and [(nbd)Rh⁺‐η⁶‐PhB^?Ph₃] ( 2 ) catalysts. The t‐Boc‐containing polymers [poly( 3a ) and poly( 4a )] were obtained in high yield (82–91%). Among the Fmoc‐protected monomers, the para‐derivative polymerized well [poly( 6a ); yield = 85–94%], whereas its meta‐substituted analogue did not afford high molecular weight polymer in good yield [poly( 5a ); yield = 10–15%]. The use of KN(SiMe₃)₂ as a cocatalyst in conjunction with 1 led to a dramatic increase in the molecular weight of the polymers. The acid‐ and base‐catalyzed removal of the t‐Boc and the Fmoc groups, respectively, generated primary amine‐containing polymers [poly( 3b )–poly( 6b )] which cannot be obtained directly by the polymerization of the corresponding monomers. The solubility characteristics of the polymers bearing protected amino groups were quite different from those of the unprotected ones, the former being soluble in polar solvents, whereas the latter displayed poor solubility even in polar protic or highly polar aprotic solvents. The attempts to accomplish the free‐standing membrane fabrication by solution casting were successful only for poly( 3a ), and an augmentation in the gas permeability and CO₂/N₂ permselectivity was discerned in comparison with the unsubstituted poly(phenylacetylene) and poly(m‐t‐butyldimethylsiloxyphenylacetylene). © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 1853–1863, 2009     

Novel optically active poly(amide-imide)s from N,N-(4,4-carbonyldiphthaloyl)-bis-l-phenylalanine diacid chloride and aromatic diamines by microwave irradiation

3,3^′,4,4^′-benzophenonetetracarboxylic dianhydride (4,4^′-carbonyldiphthalic anhydride) (1) was reacted with l-phenylalanine (2) in a mixture of acetic acid and pyridine (3:2) and the resulting imide-acid [N,N^′-(4,4^′-carbonyldiphthaloyl)-bis-l-phenylalanine diacid] (4) was obtained in high yield. The compound (4) was converted to the N,N^′-(4,4^′-carbonyldiphthaloyl)-bis-l-phenylalanine diacid chloride (5) by reaction with thionyl chloride. A new facile and rapid polycondensation reaction of this diacid chloride (5) with several aromatic diamines such as 4,4^′-diaminodiphenyl methane (6a), 2,4-diaminotoluene (6b), 4,4^′-sulfonyldianiline (6c), p-phenylenediamine (6d), 4,4^′-diaminodiphenylether (6e), m-phenylenediamine (6f), benzidine (6g) and 2,6-diaminopyridine (6h) was developed by using a domestic microwave oven in the presence of a small amount of a polar organic medium such as o-cresol. The polymerization reactions proceeded rapidly, compared with the conventional solution polycondensation, and was completed within 7 min, producing a series of optically active poly(amide-imide)s with high yield and inherent viscosity of 0.22-0.52 dl/g. All of the above polymers were fully characterized by IR, elemental analyses and specific rotation. Some structural characterization and physical properties of this optically active poly(amide-imide)s are reported.     

Novel soluble fluorinated poly(ether imide)s with different pendant groups: Synthesis,thermal, dielectric,and optical properties

Three types of new bis(ether dianhydride) monomers, [4,4′‐(2‐(3′‐methylphenyl)‐1,4‐phenylenedioxy)‐diphthalic anhydride (4a)], [4,4′‐(2‐(3′‐trifluoromethylphenyl)‐1,4‐phenylenedioxy)‐diphthalic anhydride (4b)], and [4,4′‐(2‐(3′,5′‐ditrifluoromethylphenyl)‐1,4‐phenylenedioxy)‐diphthalic anhydride (4c)] were prepared via a multistep reaction sequence. Three series of soluble poly(ether imide)s (PEIs) were prepared from the obtained dianhydrides by a two‐step chemical imidization method. Experimental results indicated that all the PEIs had glass transition temperature in the range of 200–230 °C and the temperature of 5% weight loss in the range of 520–590 °C under nitrogen. The PEIs showed excellent solubility in a variety of organic solvents due to introduction of the bulky pendant groups and were capable of forming tough films. The casting films of PEIs (80–91 μm in thickness) had tensile strengths in the range from 88 to 117 MPa, tensile modulus from 2.14 to 2.47 GPa, and elongation at break from 15 to 27%. The casting films showed UV‐Vis absorption edges at 357–377 nm, low dielectric constants of 2.73–2.82, and water uptakes lower than 0.66 wt %. The spin‐coated films of PEIs presented a minimum birefringence value as low as 0.0122 at 650 nm and low optical absorption at the optical communication wavelengths of 1310 and 1550 nm. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 3281–3289, 2010