Study of fluorescence from fluorescent dye‐based polyurethane ionomer

6‐Amino‐2‐(3‐chloro‐2‐hydroxy‐propyl)‐ benzo[de]isoquinoline‐1,3‐dione (DYE‐A) and 2‐benzyl‐6‐hydroxy‐benzo[de]isoquinoline‐1,3‐dione (DYE‐B) have been successfully synthesized in our lab, and their structures have been proven by IR, NMR, and mass spectra. The fluorescence performance appears to be better for DYE‐A than for DYE‐B as a result of DYE‐A having more electron donating substituents that are strongly excited when absorbing UV light. These fluorescent dyes have further reacted with toluene diisocyanate and other additives to form the fluorescent dye‐based polyurethane (PU) ionomer molecules, and the structures of these molecules have been demonstrated by IR spectra. In aqueous solution, our experimental results indicate that the fluorescence performance is seen to be better for DYE‐A than for DYE‐B. Increased concentration of DYE‐A molecule attached to the backbone of the PU ionomer molecule may reduce the fluorescence performance of this PU ionomer molecule, resulting from the intramolecular interaction between ionomer molecule itself. For the fluorescent dye‐based PU ionomer molecule system, the average particle size of the fluorescent dye‐based PU ionomer molecule in water increases with increasing concentration of the fluorescent dyes, as a result of increased free volume of the ionomer molecules. Our experimental results also illustrate that the tensile strength of self‐cured film made by the fluorescent dye‐based PU ionomer appears to increase with an increase in the concentration of DYE‐A. This is the result of increased intermolecular interaction between ionomer molecules. © 2003 Wiley Periodicals, Inc. J Appl Polym Sci 89: 2723–2737, 2003     

Synthesis and properties of some fluorescent 1,8‐naphthalimide derivatives and their copolymers with methyl methacrylate

Six new fluorescent derivatives of 1,8‐naphthalimide were synthesized. Three were dyes, and three were fluorescent whitening agents (FWAs) containing a tetramethylpiperidine (TMP) stabilizer fragment. The FWAs were obtained under phase‐transfer catalysis conditions. Five of the compounds were copolymerized with methyl methacrylate, so copolymers with an intense color and/or fluorescence stable against solvents were obtained. The chemical bonding of the synthesized monomers in the polymers was confirmed spectrophotometrically. The participation of the monomer compounds did not significantly affect the process of copolymerization or the molecular masses of the obtained copolymers. The quantity of chemically bonded naphthalimide monomer in the copolymers was determined to be over 60%. The spectral properties of the compounds and their photostability in solution and in the copolymers were studied. The influence of the compounds on the photostability of the copolymers was determined. The compounds, especially those containing a stabilizer (TMP) fragment in their molecules, showed a positive stabilizing effect on the photodegradation of poly(methyl methacrylate). Polyamide fabrics with 2‐allyl‐6‐hydrazino‐benzo[de]isoquinoline‐1,3‐dione, 2‐allyl‐6‐(2‐amino‐ethylamino)‐benzo[de]isoquinoline‐1,3‐dione, and 2‐chloro‐N′‐(2‐methyl)‐1,3‐dioxo‐2,3‐dihydro‐1H‐benzo[de] isoquinoline‐6‐yl) acetohydrazide were dyed, and materials with an intense yellow color and fluorescence were obtained. Cotton fabrics were whitened with 2‐(2,2,6,6‐tetramethyl‐piperidin‐4‐yl)‐6‐methoxy‐benzo[de]isoquinoline‐1,3‐dione, 2‐(2,2,6,6‐tetramethyl‐piperidin‐4‐yl)‐6‐allyloxybenzo[de]isoquinoline‐1, 3‐dione, and 2‐[2‐(2,2,6,6‐tetramethyl‐piperidin‐4‐yl)‐1,3‐dioxo‐2,3‐dihidro‐1H benzo [de]isoquinoline‐6‐oxy]ethyl‐2‐methacrylate, and materials with bright whiteness and intense bluish fluorescence were obtained. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2009     

Water vapor‐permeable polyurethane ionomer

The reaction of toluene diisocyanate with 2,2,3,3‐tetrafluoro‐1‐propanol (fluoro compound) or 3‐glycidoxypropyl trimethoxysilane(siloxane compound) and other additives to form the structure of the fluoro‐based or siloxane‐based polyurethane (PU) ionomer has been proven by infrared spectra. Experimental results indicated that the amount of water vapor permeability of the film made by fluoro‐based or siloxane‐based PU ionomer appeared to gradually increase with increasing concentration of the siloxane compound or fluoro compound, as a result of the formation of more porosities. Our experimental results also showed that the water vapor absorption was seen to be larger for the film made by siloxane‐based PU ionomer film than for the film made by fluoro‐based PU ionomer film, as a result of increased hydrophilic groups attached to the backbone of the PU ionomer molecule. For the film prepared by siloxane‐based PU ionomer, both tensile strength and elongation appeared to increase with an increase in the concentration of siloxane compound. This may be the result of the intermolecular interaction between siloxane‐based PU ionomer molecules themselves, thus enhancing the crosslinking capability of the ionomer molecules. On the other hand, both tensile strength and elongation for the film prepared by fluoro‐based PU ionomer decreased with increasing concentration of the fluoro compound, as a result of intramolecular interaction greatly reducing the crosslinking capability of the ionomer molecules. © 2006 Wiley Periodicals, Inc. J Appl Polym Sci 101: 3767–3773, 2006     

Novel regenerable N‐halamine polymeric biocides. I. Synthesis,characterization, and antibacterial activity of hydantoin‐containing polymers

Two novel cyclic‐amine monomers, i.e., 3‐allyl‐5,5‐dimethylhydantoin (ADMH) and 7,8‐benzo‐3 allyl‐1,3‐diazasprio[4.5]decane‐2,4‐dione (BADDD) were synthesized with good yields by reacting allyl bromide with 5,5‐dimethylhydantoin (DMH) and 7,8‐benzo‐1,3‐diazasprio[4.5]decane‐2,4‐dione (BDDD), respectively. The synthesized monomers were characterized by FTIR and ¹H‐NMR spectra, and copolymerized with acrylonitrile (AN), vinyl acetate (VAC), and methyl methacrylate (MMA) in a small monomer ratio of ADMH and BDDD, respectively. The copolymers were characterized by FTIR, ¹H‐NMR, and DSC studies. The N‐halamine derivatives of the corresponding copolymers were found to exhibit high antibacterial activities against Escherichia coli, and the antibacterial properties were durable and regenerable. © 2001 John Wiley & Sons, Inc. J Appl Polym Sci 80: 2460–2467, 2001     

Synthesis and characterisation of benzothiazole‐based solid‐state fluorescent azo dyes

Novel solid‐state fluorescent azo dyes containing a 2‐[4‐(dimethylamino)phenyl]benzo[d]thiazol‐6‐amine as the electron donor group were synthesised. These dyes showed a molar extinction coefficient in the range of 20 000–30 000 l/mol/cm. These compounds were characterised by strong solid‐state fluorescence under long ultraviolet light (365 nm). Absorption and fluorescence spectra revealed that electron coupling originating from broad π‐electron delocalisation and the keto–enol form is responsible for the large Stokes shift. These dyes were readily soluble in common solvents such as dichloromethane, chloroform, dimethyl formamide , tetrahydrofuran and dimethyl sulphoxide and were characterised by means of elemental analysis, proton nuclear magnetic resonance and mass spectrometry. Thermogravimetric analysis of solid‐state fluorescent dyes show thermal stability up to 270 °C and can therefore be used for polymer application. The coloristic properties of these dyes were evaluated on polyester by the disperse dyeing method.     

Synthesis,absorption spectra studies,solvatochromism and halochromism of polymethine cyanine dyes

New polymethine cyanine dyes, including tetramethine and bis‐tetramethine cyanine dyes derived from benzo[2,3‐b;2′,3′‐b′]bis‐pyrazolo[4,5‐b]‐1,4‐(oxa‐, thia‐ and pyra‐)‐zine‐6,12‐dione, were synthesised. Absorption spectra for all the synthesised cyanine dyes were examined in 95% ethanol. The solvatochromism and halochromism for some selected dyes were investigated in pure solvents and in aqueous universal buffer solutions, respectively. Structural confirmations were carried out through elemental and spectroscopic analysis.     

A study of colored siloxane-based polyurethane ionomer

The reaction of dye with toluene diisocyanate and dimethyldichlorosilane in the presence of other additives to form a colored siloxane-based polyurethane (PU) ionomer has been proven to occur by infrared spectra. In aqueous solution, the number-average particle size for the colored siloxane-based PU ionomer was found to increase with an increase in the NCO-to-OH ratio, dye concentration, and dimethyldichlorosilane concentration, as a result of increased free volume of the ionomer molecules. It is worthy to note that the amount of air diffusing into the film cast from colored siloxane-based PU ionomer was found to increase with an increase in the concentration of dimethyldichlorosilane instead of raising the ratio of NCO to OH or the concentration of dye, as a result of the formation of more porosities. In addition, the tensile strength of this film will be strengthened by raising the NCO/OH ratio or the concentration of dimethyldichlorosilane, whereas the elongation, on the other hand, can be substantially increased with increasing the concentration of dye instead of increasing the concentration of dimethyldichlorosilane for use in the PU ionomer system. © 1998 John Wiley & Sons, Inc. J Appl Polym Sci 69: 2097–2105, 1998     

Effect of dimethyldichlorosilane on the oxygen permeated through a siloxane-based polyurethane ionomer

The oxygen permeated through the film made by a polyurethane (PU) ionomer is demonstrated to be a siloxane-based polyurethane ionomer by infrared spectra. For siloxane-based polyurethane ionomer molecules in an aqueous solution, the surface tension was found to decrease slightly with an increase in the concentration of dimethyldichlorosilane (DMDCS) but to increase slightly with an increase in the ratio of NCO to OH. Owing to the increased phase volume of siloxane-based polyurethane ionomer molecules resulting from the hydrogen bonding effect and/or intermolecular interaction in the aqueous solution, the number-average particle sizes of these ionomer molecules increase considerably with an increase in the DMDCS concentration and the NCO/OH ratio, respectively. More importantly, the volume of the oxygen permeated through the film was found to be larger for the film made by the PU ionomer molecule with 0.02% (by weight) DMDCS than for the film made by the PU ionomer molecule without DMDCS. Our experimental results also suggest that the use of DMDCS in preparing siloxane-based polyurethane ionomers does substantially raise the amount of oxygen diffusing into the film made by these ionomer molecules. © 1997 John Wiley & Sons, Inc. J Appl Polym Sci 66: 981–988, 1997     

Optical sensor for aliphatic amines based on the simultaneous colorimetric and fluorescence responses of smart textile

The pH indicator proposed is a water‐soluble dye based on benzo[de]antracen‐7‐one. Dissolving in buffered aqueous solution, it changes color from yellow to orange and in the mean time decreases its fluorescence emission as a function of the amine concentration. Viscose fabric, dyed with the same dye has been investigated as a new reversible colorimetric and fluorescent sensor material for ammonia and aliphatic amines in buffered solution. The high value of the dye pK_a and the influence of the textile matrix on the selective detection of dimethylamine compared to ammonia, trimethylamine, and metylamine have been studied. The different response of the solution and textile matrix as well as the optical analyses both as a color change and a fluorescence emission have been discussed. The advantage of this sensor is the fact that depending on the analytical problem to be solved and the available instrumentation it can be used either as a fluorogenic or as a chromogenic chemosensor. In addition, the textile sensor is characterized by facile fabrication, low cost, sensibility, and reproducibility. © 2007 Wiley Periodicals, Inc. J Appl Polym Sci 2007     

Synthesis and photochemical reaction of benzo[a]quinoxalino[2,3‐c]phenazine dyes

Novel dyes based on the benzo[a]quinoxalino[2,3‐c]phenazine skeleton and necessary intermediates (benzo[a]phenazine‐5,6‐diones) were synthesized. The heterocyclic dyes and benzo[a]phenazine‐5,6‐diones were characterized using ¹H nuclear magnetic resonance (NMR) spectroscopy and chemical ion (CI) mass spectrometry. Their spectral properties, such as absorption and emission spectra and fluorescence quantum yield, were also measured. Experimental results demonstrated that photolysis of benzo[a]quinoxalino[2,3‐c]phenazine dyes in 2‐propanol and cyclohexene oxide leads to dihydro derivatives. The same product is formed during irradiation of dye/iodonium salt photoredox pairs in monomers. These compounds absorb incident light at longer wavelength and act as in situ sensitizers. Thus, when a composition was irradiated with a xenon lamp through a 395 cutoff filter, higher conversion was achieved than under monochromatic light.     

Synthesis and application of dyes derived from benz[cd]indol‐2(1H)‐one as visible‐light‐absorbing polymerisation photoinitiators

Several potential initiators based on benz[cd]indol‐2(1H)‐one dye have been synthesised and evaluated in the radical polymerisation of a system containing trimethylolpropane triacrylate under visible light. Absorption, fluorescence, and phosphorescence spectra and the electrochemical properties of these novel dyes were determined. Owing to the presence of an appropriate hydrogen donor group in their structure, these photoinitiators do not need an extra coinitiator to initiate the polymerisation process. During photopolymerisation they act both as a triplet sensitiser and as a hydrogen donor. The relationship between the polymerisation rate and the triplet‐excited‐state reduction potential suggests that initiating radicals are formed from the triplet state via hydrogen transfer. This mechanism is supported by density functional theory calculations. 8‐Bromo‐6‐[(2‐sulphanylethyl)sulphanyl]benzo[cd]indol‐2(1H)‐one and 8‐bromo‐6‐sulphanylbenz[cd]indol‐2(1H)‐one may be applied as visible‐light initiators of free radical polymerisation to obtain a low‐molecular‐weight polymer.     

Study on the dyeing properties of hemicyanine dyes. II. Cationic dyeable polyester

The absorption spectra of two hemicyanine fluorescent dyes, namely, trans‐4‐[p‐(N,N‐di(2‐hydroxyethyl))‐amino‐styryl]‐N‐ethyl pyridinium bromide (DHEASPBr‐C₂) and trans‐4‐[p‐(N,N‐di(2‐hydroxyethyl))‐amino‐styryl]‐N‐octyl pyridinium bromide (DHEASPBr‐C₈), were studied at various levels of pH and high temperatures, and were then employed to dye cationic dyeable polyester. Their dyeing properties, fluorescent reflectance and colorimetric properties were explored. The novel fluorescent dyes existed in two forms of monocation and dication in solutions at low pH and high temperature. Overall, the influence of pH on colour depth and the maximum reflectance of dyed cationic dyeable polyester was extremely small. The adsorption mechanism of DHEASPBr‐C₂ and DHEASPBr‐C₈ on cationic dyeable polyester fibres was in good accord with the Langmuir type. Compared with DHEASPBr‐C₂, DHEASPBr‐C₈ exhibited comparatively faster adsorption rate, higher affinity and dye uptake, while its fluorescence shown by cationic dyeable polyester was slightly weak.     

Tunable solid‐state fluorescence emission and red upconversion luminescence of novel anthracene‐based fluorophores

Novel, tunable solid‐state emitters based on anthracene groups were synthesised and characterised by spectroscopy and elemental analysis. Their solid‐state photoluminescence properties were studied. These fluorophores display interesting solid‐state emission properties with an emission at wavelengths ranging from 550 to 650 nm when excited by a 325 nm helium–cadmium laser at room temperature. In particular, among them, 1,6‐di(9‐anthryl)hexa‐1,5‐diene‐3,4‐dione, 2‐[4‐(2‐benzoxazolyl)phenyl]‐4,5‐bis[2‐(9‐anthryl)vinyl]‐1H‐imidazole and 2,3‐bis[2‐(9‐anthryl)vinyl]quinoxaline show red, yellow and green emission, respectively, at 650, 584 and 550 nm. The results demonstrated that the luminescent colours can be tuned from red to yellow and green by simply varying molecular structure. Besides, 1,6‐di(9‐anthryl)hexa‐1,5‐diene‐3,4‐dione also exhibited an upconverted red fluorescent emission peak at around 675 nm under femtosecond excitation at 800 nm.     

Tuning the Hydrophobicity of a Mitochondria‐Targeted NO Photodonor

A few compounds in which the nitric oxide (NO) photodonor N‐[4‐nitro‐3‐(trifluoromethyl)phenyl]propane‐1,3‐diamine is joined to the mitochondria‐targeting alkyltriphenylphosphonium moiety via flexible spacers of variable length were synthesized. The lipophilicity of the products was evaluated by measuring their partition coefficients in n‐octanol/water. The obtained values, markedly lower than those calculated, are consistent with the likely collapsed conformation assumed by the compounds in solution, as suggested by molecular dynamics simulations. The capacity of the compounds to release NO under visible light irradiation was evaluated by measuring nitrite production by means of the Griess reaction. The accumulation of compounds in the mitochondria of human lung adenocarcinoma A549 cells was assessed by UPLC–MS. Interestingly, compound 13 [(9‐((3‐((4‐nitro‐3‐(trifluoromethyl)phenyl)amino)propyl)amino)‐9‐oxononyl) triphenylphosphonium bromide] displayed both the highest accumulation value and high toxicity toward A549 cells upon irradiation‐mediated NO release in mitochondria.     

Synthesis of anionic water‐borne polyurethane with the covalent bond of a reactive dye

We successfully synthesized an anionic water‐borne polyurethane (PU) capable of reacting with a reactive dye to form a covalent bond with the dye molecule. The anionic water‐borne PU was synthesized and grafted with the reactive dye to form a dyed PU. First, the PU prepolymer was synthesized from 4,4′‐methylene bis(isocyanatocyclohexane), poly(tetramethylene glycol), 2,2′‐bis(hydroxymethyl) propionic acid (as an anionic center), and triethyleneamide (as a neutralizer). Then, pure water was added to emulsify and disperse the prepolymer to form an anionic water‐borne PU prepolymer. Finally, the extender N‐(2‐hydroxyethyl) ethylene diamine was used to extend the anionic water‐borne prepolymer to form a PU polymer with hydroxyl groups that could further react with the reactive dye molecule. With respect to the heating properties, the dyed PU polymers exhibited higher glass‐transition temperatures of the hard segment than those without dye molecules. However, neither the glass‐transition temperature of the soft segment nor the melting temperature of the soft segment varied in the presence of dye molecules, but they were changed with various chain lengths of the soft segment. As for the mechanical properties, the modulus and strength of the dyed PU polymers decreased because of the bulkiness of their dye molecules, but the breaking elongation increased. Moreover, the inherent viscosity decreased in the presence of the dye molecules. As for the dyeing properties, the percentage of dye grafting was greater than 90%. The dye‐grafted PU exhibited a lower percentage of migration than PU extended with ethylene diamine (without hydroxy groups) and also showed a higher grade of colorfastness to light. © 2002 John Wiley & Sons, Inc. J Appl Polym Sci 84: 797–805, 2002; DOI 10.1002/app.10336     

Synthesis,characterization and fluorescence performance of a waterborne polyurethane‐based fluorescent dye 4‐amino‐N‐cyclohexyl‐1,8‐naphthalimide,WPU‐ACN

A waterborne‐polyurethane‐based fluorescent dye 4‐amino‐N‐cyclohexyl‐1,8‐naphthalimide (WPU‐ACN) was synthesized by attaching 4‐amino‐N‐cyclohexyl‐1,8‐naphthalimide (ACN) into polyurethane chains according to a prepolymer?ionomer process. The structure of WPU‐ACN was confirmed by means of Fourier transform infrared spectroscopy and UV?visible absorption. The number‐average molecular weight, glass transition temperature and average emulsion particle size for WPU‐ACN were determined as 7.8 × 10⁵ g mol^?1, 60 °C and 60 nm, respectively. The improved thermal stability of WPU‐ACN could be attributed to the incorporation of naphthalimide units in the preformed urethane groups. The fluorescence intensity of WPU‐ACN was dramatically enhanced compared with that of ACN. It was found that the fluorescence intensity of WPU‐ACN increased with increasing temperature, and the fluorescence spectra of WPU‐ACN showed a positive solvatochromic effect. In addition, the fluorescence of WPU‐ACN emulsion was very stable not only for long‐term storage but also for fluorescence quenching. © 2013 Society of Chemical Industry     

ω‐Phthalimidoalkyl Aryl Ureas as Potent and Selective Inhibitors of Cholesterol Esterase

Cholesterol esterase (CEase), a serine hydrolase thought to be involved in atherogenesis and thus coronary heart disease, is considered as a target for inhibitor development. We investigated recombinant human and murine CEases with a new fluorometric assay in a structure–activity relationship study of a small library of ω‐phthalimidoalkyl aryl ureas. The urea motif with an attached 3,5‐bis(trifluoromethyl)phenyl group and the aromatic character of the ω‐phthalimide residue were most important for inhibitory activity. In addition, an alkyl chain composed of three or four methylene groups, connecting the urea and phthalimide moieties, was found to be an optimal spacer for inhibitors. The so‐optimized compounds 2 [1‐(3,5‐bis(trifluoromethyl)phenyl)‐3‐(3‐(1,3‐dioxoisoindolin‐2‐yl)propyl)urea] and 21 [1‐(3,5‐bis(trifluoromethyl)phenyl)‐3‐(4‐(1,3‐dioxoisoindolin‐2‐yl)butyl)urea] exhibited dissociation constants (K_i) of 1–19 μm on the two CEases and showed either a competitive ( 2 on the human enzyme and 21 on the murine enzyme) or a noncompetitive mode of inhibition. Two related serine hydrolases—monoacylglycerol lipase and fatty acid amide hydrolase—were inhibited by ω‐phthalimidoalkyl aryl ureas to a lesser extent.     

Synthesis and characterization of macroporous silica modified with optically active poly[N‐(oxazolinylphenyl)acrylamide] derivatives for potential application as chiral stationary phases

Enantiopure acrylamide derivatives, (S)‐N‐[o‐(4‐methyl‐4,5‐dihydro‐1,3‐oxazol‐2‐yl)phenyl]acrylamide and (R)‐N‐[o‐(4‐phenyl‐4,5‐dihydro‐1,3‐oxazol‐2‐yl)phenyl]acrylamide, were synthesized through the acylation of chiral 2‐oxazolinylanilines. The radical polymerization of the chiral monomers was carried out with (3‐mercaptopropyl)trimethoxysilane as a chain‐transfer agent to obtain the corresponding optically active prepolymers with a trimethoxysilyl group. By immobilizing the prepolymers on porous silica gel via the grafting‐to method, we prepared a new chiral stationary phase (CSP) and characterized it by elemental analysis, thermogravimetry, and Fourier transform infrared spectroscopy. The enantioseparation capacities of the CSPs were evaluated with high‐performance liquid chromatography toward several racemic compounds, including 1,1′‐bi‐2‐naphthol, benzoin, 2‐amino‐1‐butanol, and loxoprofen sodium under the normal‐phase mode. The results indicate that the CSPs exhibited improved chromatographic performances compared to their brush‐type analogs obtained by the alternative grafting‐from approach. Also, the column packed with poly{(R)‐N‐[o‐(4‐phenyl‐4,5‐dihydro‐1,3‐oxazol‐2‐yl)phenyl]acrylamide}‐bonded silica was found to have an extent of enantioselectivity in the chiral resolution of some unmodified amino acids with reversed‐phase eluents. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2010     

Tautomerism,crystal structure,and copper(II) complexation of isomeric pyridonylazo dyes derived from 2‐ and 4‐aminobenzoic acids

A pair of isomeric aromatic heterocyclic dyes, bearing the same N‐methyl pyridine‐2,6‐dione coupling component but a different 2‐ or 4‐aminobenzoic acid diazo component, were characterised structurally and spectroscopically. X‐ray single‐crystal diffraction analyses revealed that they both adopt the same hydrazone‐tautomeric form and planar molecular conformation between the pyridine and phenyl rings. Furthermore, azo–hydrazone transformation was achieved for the 2‐aminobenzoic‐acid‐based dye after Cu(II) ion complexation, as verified by the formation of a neutral Cu(II) dye–metal complex. The coordination geometry of the central Cu(II) ion exhibits a slightly distorted pyramid with a value of 0.028, where the ligand loses a proton during complexation and serves as the tridentate coordination mode. In addition, thermogravimetric analysis and corresponding differential thermal analysis for the isomeric pair showed that they both have excellent thermal stability, and 4‐aminobenzoic‐acid‐based dye has a higher decomposition temperature (319 °C) than the 2‐aminobenzoic‐acid‐based dye (312 °C). To the best of our knowledge, this is the first structural study on aromatic heterocyclic dyes having aminobenzoic acid and pyridine‐2,6‐dione components at the same time.     

Processable high Tg high strength fluorinated new poly(arylene ether)s containing imido aryl group

A series of poly(arylene ether)s ( 7a–7f ) were successfully synthesized by aromatic nucleophilic substitution reactions of imidoaryl biphenol (5), 4,9‐bis‐(4‐hydroxy‐phenyl)‐2‐phenyl‐benzo[f]isoindole‐1,3‐dione with six different trifluoromethyl substituted bisfluoro monomers ( 6a–6f ). The weight‐average molar masses of the polymers were up to 280 kD as measured by GPC. These poly(arylene ether)s exhibited glass transition temperatures up to 361°C in DSC. These polymers showed very high thermal stability up to 558°C for 10% weight loss under synthetic air in TGA. Except 7d–7f, remaining polymers 7a–7c were soluble in a wide range of organic solvents. Transparent thin films of these polymers cast from DCM or NMP exhibited tensile strengths up to 75 MPa and elongation at break up to 41% depending on their exact repeating unit structures. These poly(arylene ether)s showed cut‐off wavelength in between 400 and 450 nm except 7d and water absorption were in the range of 0.4 to 0.6%. © 2011 Wiley Periodicals, Inc. J Appl Polym Sci, 2011