Highly Refractive and Transparent Polyimides Derived from 4,4‘-[<i>m</i>-Sulfonylbis(phenylenesulfanyl)]diphthalic Anhydride and Various Sulfur-Containing Aromatic Diamines

Suzuki, Yasuo; Liu, Jingang; Nakamura, Yasuhiro; Shibasaki, Yuji; Ando, Shinji; Ueda, Mitsuru

doi:10.1021/ma0713714

Cited by 109 publications

(100 citation statements)

References 38 publications

(57 reference statements)

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“…[22][23][24][25][26] It was proved that these copolymer networks are electrochemically active and can be used in cathodes of Li-S batteries with enhanced charge capacity and lifetime (1000 mA h g 21 and 500 charge-discharge cycles were measured with the produced batteries). [22][23][24][25][26] Moreover, it was showed that these sulfur-rich copolymer networks present interesting properties as high refractive index polymers (HRIP) [22][23][24]27 with important applications in advanced optoelectronic fabrications (e.g., advanced displays, OLEDs, and antireflective coatings [28][29][30] ). The design of copolymer network composition (through the initial S/crosslinker ratio) is an important issue in order to tailor the properties of the final materials.…”

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confidence: 99%

Electrochemical activity of sulfur networks synthesized through RAFT polymerization

Almeida

Costa

Kadhirvel

et al. 2016

J of Applied Polymer Sci

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Novel results concerning the inverse vulcanization of sulfur using reversible addition-fragmentation chain transfer (RAFT) polymerization are here reported. It is shown that RAFT polymerization can be used to carry out this cross-linking process, with the additional possibility to extend the reaction time from a few minutes as with classical free radical polymerization (FRP) to several hours. Higher control on viscosity and processability of the synthesized networks, as well as, the implementation of semibatch feed policies during cross-linking are important advantages of the RAFT process here explored comparatively to the FRP inverse vulcanization. Using cyclic voltammetry, it was assessed the electrochemical activity of the synthesized sulfur-rich polymer networks. It is shown that the fundamental electrochemical activity of the elemental sulfur was preserved in the produced materials. Testing of electrochemical cells assembled with lithium in the anode and different sulfur based materials in the cathode, including the synthesized RAFT networks, is also shown. The results here presented highlight the new opportunities introduced by reversible-deactivation radical polymerization mechanisms on the control of the synthesis process and in the design of such advanced materials and show also that many potential derivatizing possibilities can be achieved.

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confidence: 99%

Electrochemical activity of sulfur networks synthesized through RAFT polymerization

Almeida

Costa

Kadhirvel

et al. 2016

J of Applied Polymer Sci

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“…These systematic decreases are essentially attributable to the lower polarizability per unit volume of sulfonyl linkage than that of -S-linkage. As discussed in our previous report, 11 the two oxygen atoms in sulfonyl linkage significantly increase the molecular volume of the linkage and reduce the content of polarizable sulfur atoms in the PIs. In addition, sulfonyl linkage renders reduction of the intermolecular CTC formation and the electron-donating ability of the diamine.…”

Section: Optical Properties Of Pismentioning

confidence: 51%

“…10 To remedy this problem, we reported highly refractive and transparent PIs derived from 4,4 0 -[m-sulfonylbis(phenylenesulfanyl)]diphthalic anhydride (mDPSDA) and various sulfurcontaining aromatic diamines. 11 The average refractive index (n av ) measured at 632.8 nm range from 1.7162 to 1.7432 depending on the different sulfur contents of PIs, and the metasubstituted electron-withdrawing sulfonyl moiety endowed PI films with good optical transparency. The optical transmittances of the PI films at 450 nm are higher than 85% for the thickness of ca.…”

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confidence: 99%

Synthesis of Highly Refractive and Transparent Polyimides Derived from 4,4′-[p-Sulfonylbis(phenylenesulfanyl)]diphthalic Anhydride and Various Sulfur-containing Aromatic Diamines

Suzuki

Liu

Nakamura

et al. 2008

Polym J

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Highly refractive and transparent polyimides (PIs) have been developed. The PIs were prepared from a para-substituted sulfonyl-bridged dianhydride, 4,4 0 -[p-sulfonylbis(phenylenesulfanyl)]diphthalic anhydride (p-DPSDA) and various sulfurcontaining aromatic diamines including 4,4 0 -thiobis [(p-phenylenesulfanyl)aniline] (3SDA), 4,4 0 -sulfonylbis[(p-phenylenesulfanyl)aniline] (BADPS), and 2,7-bis(p-aminophenylenesulfanyl)thianthrene (APTT) by employing a two-step polycondensation procedure. The PIs showed excellent thermal stabilities with 5% weight loss temperatures (T d 5 ) exceeding 470 C in nitrogen and the glass transition temperatures (T g s) higher than 208 C. The PI films exhibited good optical transmittances exceeding 85% at 450 nm and high refractive indices of 1.7169-1.7420 at 632.8 nm that are almost same as those of the PIs derived from 4,4 0 -[m-sulfonylbis(phenylenesulfanyl)]diphthalic anhydride (mDPSDA). The para-substituted electron-withdrawing sulfonyl moiety improves the transparency but lowers the refractive index. In addition, very small birefringence (Án) of 0.0065-0.0093 was obtained for the PIs.KEY WORDS: Sulfur-containing Polyimide / High Refractive Index / Transparency / Thermal Stability / Polyimides (PIs) are a class of polymers extensively used in microelectronics because of their outstanding key properties such as high thermal stabilities, chemical resistance, and good mechanical and excellent electrical properties.1 They are used as interlayer dielectrics in integrated circuit fabrication. Recently, high refractive index PIs are increasingly noticed for microlens components for charge coupled device (CCD) or complementary metal oxide semiconductor (CMOS) image sensors because of their excellent properties described above and inherent high refractive index.2 Chen et al. prepared high refractive index aminoalkoxysilane-capped pyromellitic dianhydride (PMDA)-titania hybrid optical thin films from PMDA, aminopropyltrimethoxysilane, and titanium (IV) isopropoxide via a sol-gel process. The refractive indices of these hybrid optical thin films were in the range of 1.567 to 1.780 depending on the titania contents.3 The syntheses of similar PIs/titania hydrid thin films were also reported in several papers.4,5 However, high refractive index PIs for microlens are required to have a good pattern formability by the conventional photolithography technique as well as low birefringence (Án), good transparency in the visible light region, and high thermal stability.Based on these backgrounds, we have been interested in developing practical high-n polymers, sulfur-containing PIs, and reported several PIs containing thioether linkages, either linear 6,7 or cyclic. 8,9 Refractive indices as high as 1.76 at the wavelength of 632.8 nm, and in-plane/out-of-plane birefringences lower than 0.01 have been successfully achieved.9 For fabricating optical devices, optical transparency might be one of the most serious obstacles for high-n PIs. The formation of intermolecular or intramolecular charge transfer...

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“…The sulfone materials have been applied to various high-performance engineering materials, such as fuel cell membranes, [17][18][19] gas separation membranes, 20,21 optical or photo materials, 22,23 etc. Because of the sulfonyl materials incorporated with the polymer materials, which could improve the thermal and oxidative stability, chemical resistance, and the glass transition temperature (T g ).…”

Section: Introductionmentioning

confidence: 99%

Intermolecular force and thermal properties of the sulfonyl epoxy blends cured with DGEBA epoxy

Chiu¹,

Tsai²,

Chou³

et al. 2010

J of Applied Polymer Sci

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The sulfonyl epoxy monomer (SEP) was synthesized and further to blend with the diglycidyl ether of bisphenol A (DGEBA). The glass transition temperature (T g ) of the SEP/DGEBA blended materials increased from 103.7 to 163.8 C. The cross-linking density and polymer chain self-association intra-molecular action affected more than that the polymer-polymer intermolecular action (hydrogen bonding) in the SEP blended with the DGEBA materials. The excess stabilization energy in the overall stabilization was only 0.00145% (14.5 ppm), which indicated that the polymer-polymer intermolecular action was weak. The thermal degradation of the SEP segments could form various sulfate derivatives at lower temperature and analyzed by the TGA/GC/Mass. The sulfate derivatives could generate the thermal stable chars, which provided the ''shielding effect'' and antioxidation property. Additionally, these chars could also improve the protective effect and inhibit the thermal-oxidation decomposition under the air atmosphere.

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Highly Refractive and Transparent Polyimides Derived from 4,4‘-[m-Sulfonylbis(phenylenesulfanyl)]diphthalic Anhydride and Various Sulfur-Containing Aromatic Diamines

Cited by 109 publications

References 38 publications

Electrochemical activity of sulfur networks synthesized through RAFT polymerization

Electrochemical activity of sulfur networks synthesized through RAFT polymerization

Synthesis of Highly Refractive and Transparent Polyimides Derived from 4,4′-[p-Sulfonylbis(phenylenesulfanyl)]diphthalic Anhydride and Various Sulfur-containing Aromatic Diamines

Intermolecular force and thermal properties of the sulfonyl epoxy blends cured with DGEBA epoxy

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