Synthesis and characterization of soluble polyimides from 2,2-bis(4-aminophenyl)cycloalkane derivatives

New aromatic diamines [(1) and (2)] containing polycycloalkane structures between two benzene rings were synthesized by HCl-catalyzed condensation reaction of aniline hydrochloride and corresponding polycycloalkanone derivatives. The structures of diamines were identified by H-1-NMR, C-13-NMR, FTIR spectroscopy, and elemental analysis. The polyimides were synthesized from the obtained diamines with various aromatic dianhydrides by one-step polymerization in m-cresol. The inherent viscosities of the resulting polyimides were in the range of 0.34-1.02 dL/g. The polyimides showed good thermal stabilities and solubility. All the polymers were readily soluble in N-methyl-2-pyrrolidone, m-cresol, tetrachloroethane, etc. Some of them were soluble even in chloroform at room temperature. The glass transition temperatures were observed in the range of 323-363 degrees C, and all of the polymers were stable up to 400 degrees C under nitrogen atmosphere. (C) 1999 John Wiley & Sons, Inc.

Water soluble polyaniline and its blend films prepared by aqueous solution casting

Polyaniline (PAn) was doped with phosphonic acid containing hydrophilic tails. The solubility of the doped PAn in water was controlled by changing the length of hydrophilic chain in the dopant. When poly(ethylene glycol) monomethyl ether (PEGME) with molecular weight M-w = 550 was used as the hydrophilic chain of the dopant, the doped PAn was entirely soluble in water. The film cast from aqueous solution showed good electrochemical redox reversibility, Aqueous solution blending of PAn with poly(ethylene glycol) (PEG, M-w = 20 000) and poly(N-vinyl pyrrolidone) (PVP, M-w = 360 000) was achieved. Percolation threshold of the composite film was lower than 3 wt.%. Electrical conductivity of the composite film was in the range of 10(-1)-10(-5) S cm(-1), depending on molecular weight of the acid and the content of PAn in the composite. (C) 1999 Elsevier Science Ltd. All rights reserved.

Soluble 2,5-dimercapto-1,3,4-thiadiazole/poly(o-toluidine) electroactive composite

A poly(o-toluidine) (POT)/2,5-dimercapto-1,3,4-thiadiazole (DMcT) composite was prepared. When POT and DMcT are mixed in a proper solvent, POT in a medium-oxidation state is reduced, and DMcT in turn is oxidized to its soluble dimer when the molar ratio of DMcT to POT is higher than 0.5. Therefore, the composite was soluble in organic solvents such as tetrahydrofuran (THF), dimethylformamide (DMF), and N-methyl-2-pyrrolidone (NMP) and exhibited very high electroactivity, two orders of magnitude higher than that of pure POT and three orders of magnitude higher than that of pure DMcT. Molecular-level contact between POT and DMcT is the reason for the improved catalytic effect of POT on DMcT, compared to that of polyaniline on DMcT. (C) 1999 The Electrochemical Society. S0013-4651(98)08-059-8. All rights reserved.

Synthesis and characterization of a water-soluble endohedral metallofullerol

A water-soluble endohedral metallofullerol, Pr@C82Om(OH)(n)(m approximate to 10 and n approximate to 10), was successfully synthesized through the reaction of a pure endohedral metallofullerene, Pr@C-82, with a concentrated nitric acid and a subsequent hydrolysis process. The formation of endohedral metallofullerols Pr@C82Om(OH)(n) is thought to involve a NO2 radical formation step, in much the same way as the reaction of empty fullerenes. FT-IR, XPS, and LD-TOF MS techniques were employed to characterize the structure of the endohedral metallofullerol from the above reaction.

A comparative study of insoluble and soluble polyimide thin films

Physical properties of thin films of soluble and insoluble aromatic polyimides were compared by d.s.c., u.v.-visible and fluorescence spectroscopy, and prism coupler technique. D.s.c. results showed that the thermal properties of insoluble polyimides are superior to those of soluble ones, owing to the specific molecular interactions of insoluble polyimides, revealed by fluorescence spectroscopy. However, the specific molecular interactions sacrifice the transparency in their thin films, shown by u.v.-visible transmission spectra. Negative birefringence of thin films, not only for soluble polimides but also for polyamic acids of insoluble polyimides, was confirmed by prism coupler, while thin films of insoluble polyimides thermally imidized lack high levels of negative birefringence. It is regarded that thin films of insoluble polyimides thermally imidized are likely to be isotropic because of molecular relaxation above their glass transition temperatures (T-g) in the course of thermal imidization, according to Flory's principle. On the contrary, thin films of insoluble poyimide chemically imidized keep the same levels of negative birefringence as those of the relevant polyamic acid thin films. Judging from the opposite cases, it is recognized that molecular relaxation above T-g weakens the optical anisotropy of polyimide thin films. (C) 1998 Elsevier Science Ltd. All rights reserved.

Study on mixed Langmuir-Blodgett film of tri-(2,4-di-t-amylphenoxy)-(8-quinolinolyl)copper phthalocyanine and water-soluble fullerenols

Mixed Langmuir-Blodgett films of tri-(2,4-di-t-amylphenoxy)-(8-quinolinolyl) copper phthalocyanine and water-soluble fullerenols are prepared. Their behavior at the air-water interface and the monolayer morphology are studied. (C) 1998 Elsevier Science Limited. All rights reserved.

Soluble and colorless polyimides from alicyclic diamines

A series of novel polyimides was synthesized from alicyclic diamines and various aromatic dianhydrides by one-step polymerization in m-cresol without a catalyst. The polymerization was conducted for 4 hours with refluxing, which was enough to obtain the polymers with high molecular weight. The inherent viscosities of the resulting polyimides were in the range of 0.30 similar to 1.29 dL/g. The prepared polyimides showed excellent thermal stabilities and good solubility. All the polymers were readily soluble in common organic solvents such as chloroform, tetrachloroethane (TCE), dimethylacetamide (DMAc), etc and the glass transition temperatures were observed at 199 to 311 degrees C. UV-visible spectra were obtained to measure the transparency of polymer films. All the polymers showed high transmission above 90% in the wavelength of 400 similar to 700 nm.

Bright red organic electroluminescent devices based on a soluble rare earth complex Eu(TTA)(3) Phen

An Electroluminescent device with PVK film doped with Eu(TTA)(3) Phen and PBD was fabricated. The device structure of glass substrate/indium-tin-oxide/PPV/PVK : Eu(TTA)3 Phen : PBD/Alq(3)/Al was employed. A sharply red electroluminescence with a maximum luminance of 56. 8 cd/m(2) at 48 V was achieved.

Optical properties of organo-soluble polyimide thin films and their applications in liquid crystal displays

Three organo-soluble polyimide powders have been synthesized. Their imidization was verified by Fourier transform infrared (FTIR) and thermal gravimetric analysis (TGA) techniques. The amorphous morphology of their thin films were confirmed by X-ray diffraction. Polyimide thin films were prepared by solution casting or spin coating. UV-visible transmission spectra of thin films revealed that they are almost transparent in the range of visible light. With in-plane orientation, revealed by FTIR spectra, negative birefringence (Delta n) of thin films were observed, and refractive indices of the thin films along the film plane (n(TE)) and normal to the plane (n(TM)) were measured by a prism coupler. Because of negative birefringence of the thin films, they tan be substituted for the compensation films for twisted nematic liquid crystal displays (TN-LCDs) to extend their viewing angles. In this paper, a 90 degrees C TN-LCD and 120 degrees C TN-LCD were taken as examples to show the compensation effect of thin films of a qualified polyimide. (C) 1998 Elsevier Science S.A. All rights reserved.

Bright red electroluminescent devices based on a soluble lanthanide complex Eu(DBM)(3)(phen)

Electroluminescent devices with PVK film doped with Eu(DBM)(3)(phen) and PBD were fabricated. The device structure of glass substrate/indium-tin-oxide/PPV/PVK:Eu(DBM)(3)-(phen):PBD/Alq(3)/Al was employed. The emissive layer was formed by spin-casting method. A sharply red electroluminescence with a maximum luminance of 114.4 cd/m(2) was achieved at 42 V.

The electrochemical behaviour of soluble polyimides

The electrochemical behaviour of five soluble polyimides was studied in organic solution using cyclic voltammetry. The relationship between the electrochemical behaviour and the molecular structure was discussed, It was found that the colours of polyimides can be changed due to the electrochemical redox reactions.

Synthesis and high efficiency green light-emitting diode of a soluble polymer

A soluble polymer emitting green color with high efficiency was synthesized. Bright green electroluminescence devices, both single layer and multilayer, were fabricated. The luminous efficiency was improved dramatically. Carrier injection from the electrodes to the emissive layer and concomitant green electroluminescence from the emissive layer were observed. A luminance of 920 cd/m(2) and luminous efficiency of 5.35 1m/W were achieved at a drive voltage of 15 V for the multilayer device. (C) 1997 Elsevier Science S.A.

Synthesis and solvent enhanced relaxation property of water-soluble endohedral metallofullerenols

Gadolinium fullerenols, as novel and potential contrast agents for magnetic resonance imaging, were synthesized, which showed excellent efficiency in enhancing water proton relaxation with a relaxivity of 47.0+/-1.0 mM(-1).s(-1).

Gas separation with organo-soluble high performance aromatic polyimide films

An organo-soluble polyimide based on 4,4'-(1,4-phenylenedioxy)diphthalic anhydride and 2,2'-dimethyl-4,4'-methylenedianiline was synthesized by two-step polycondensation accompanied by chemical imidization. Polyimide films were prepared by spray casting onto glass substrates. The study focused on the separation of carbon dioxide (CO2) from natural gas and the enrichment of methane (CH4) from butane (C4H18). The permeability and permselectivity coefficients of these gases were determined.