A study on the effect of spirocyclic structures in the main chain on the physical properties of copolyimides

Li, Jun; Kudo, Kazuaki; Shiraishi, Shinsaku

doi:10.1002/1521-3927(20001101)21:16<1166::aid-marc1166>3.0.co;2-m

Cited by 17 publications

(6 citation statements)

References 18 publications

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“…We have previously reported the synthesis of rac ‐DAn from itaconic anhydride in three steps 6. The synthetic route includes the Diels–Alder reaction with cyclopentadiene, the oxidative cleavage of the CC bond in the adduct, and the subsequent dehydrative ring closure.…”

Section: Resultsmentioning

confidence: 99%

“…With this Diels–Alder adduct in hand, we proceeded to synthesize the optically active dianhydride according to the method we had reported, as shown in Scheme 6. Esters were hydrolyzed under basic conditions to give a dicarboxylic acid.…”

Section: Resultsmentioning

confidence: 99%

“…On the other hand, we have reported the preparation of alicyclic PIs from a tetracarboxylic dianhydride, [1 S *,5 R *,6 S *]‐3‐oxabicyclo[3.2.1]octane‐2,4‐dione‐6‐spiro‐3′‐(tetrahydrofuran‐2′,5′‐dione) (DAn), with a spirocyclic framework and chirality 6–8. In a previous article, we described the synthesis of constitutionally isomeric PIs, including head‐to‐head, head‐to‐tail, and random PIs with rac ‐DAn and p ‐phenylenediamine 8.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of optically active alicyclic polyimides from a chiral, nonracemic dianhydride

Kudo

Nonokawa

et al. 2002

J. Polym. Sci. A Polym. Chem.

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Optically active alicyclic polyimides were prepared for the first time from (−)‐[1S*,5R*,6S*]‐3‐oxabicyclo[3.2.1]octane‐2,4‐dione‐6‐spiro‐3′‐(tetrahydrofuran‐ 2′,5′‐dione) [(−)‐DAn] via polycondensation with diamines and subsequent chemical or thermal imidization. The dianhydride (−)‐DAn was synthesized by an asymmetric Diels–Alder reaction of a chiral itaconic acid derivative as a key step. Colorless or slightly yellow flexible films were obtained for the (−)‐DAn‐derived polyimides {PI[(−)‐DAn]s}. PI[(−)‐DAn]s showed good solubility toward dipolar aprotic solvents and pyridine. For 1,4‐dioxane and chloroform, the optically active polyimides showed slightly better solubility than the corresponding polyimides prepared from rac‐DAn [PI(rac‐DAn)s]. PI[(−)‐DAn]s showed glass‐transition temperatures of 267–268 °C and 10% weight‐loss temperatures of 416–424 °C in nitrogen. These values were almost identical to those of PI(rac‐DAn)s. The circular dichroism spectra of PI[(−)‐DAn]s showed exciton coupling patterns indicating that to some extent these polyimides had a higher order structure in solution. © 2002 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 40: 4038–4044, 2002

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of optically active alicyclic polyimides from a chiral, nonracemic dianhydride

Kudo

Nonokawa

et al. 2002

J. Polym. Sci. A Polym. Chem.

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“…Kudo's group also successfully synthesized a series of optically active and soluble PIs having a spiro alicyclic unit in the main chain by the reactions of DAn with several diamines through a general two-step polymerization method [121][122]. In another research, they reported on a systematic investigation of the physical properties of coPIs of DAn [123]. The comonomer used in their study was c-3-carboxymethyl-r-1,c-2,c-4-cyclopentane tricarboxylic acid 1,4:2,3-dianhydride (TCAAH), a structural isomer of DAn, which is unsymmetric but does not have a spiro unit (see Figure 10).…”

Section: Polyimidesmentioning

confidence: 99%

“…Synthesis of optically active coPIs derived from DAn [119][120][121][122][123] DMF system as condensing agent. The resulting polymers were obtained in good yields with inherent viscosities ranging between 0.21 and 0.61 dL/g.…”

Section: Polyestersmentioning

confidence: 99%

Advances in synthetic optically active condensation polymers - A review

Mallakpour

Zadehnazari²,

Iran³

2011

Express Polym. Lett.

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Abstract. The study of optically active polymers is a very active research field, and these materials have exhibited a number of interesting properties. Much of the attention in chiral polymers results from the potential of these materials for several specialized utilizations that are chiral matrices for asymmetric synthesis, chiral stationary phases for the separation of racemic mixtures, synthetic molecular receptors and chiral liquid crystals for ferroelectric and nonlinear optical applications. Recently, highly efficient methodologies and catalysts have been developed to synthesize various kinds of optically active compounds. Some of them can be applied to chiral polymer synthesis. In a few synthetic approaches for optically active polymers, chiral monomer polymerization has essential advantages in applicability of monomer, apart from both asymmetric polymerization of achiral or prochiral monomers and enantioselective polymerization of a racemic monomer mixture. The following are the up to date successful approaches to the chiral synthetic polymers by condensation polymerization reaction of chiral monomers.

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Preparation and characterization of new inorganic–organic hybrid catalyst H₃PMo₁₂O₄₀/Hyd‐SBA‐15 and its application in the domino multi‐component reaction

Safaei‐Ghomi

Bakhtiari

2019

Applied Organom Chemis

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We present novel inorganic-organic hybrid catalyst to accomplish domino multi-component reaction (MCR) for synthesis of 3-amino-2′-oxospiro[benzoThis methodology offers remarkable development by easy production of H 3 PMo 12 O 40 /Hyd-SBA-15 in regard to solving the problem of using harsh catalysts, also it demonstrates to be impressive and environmentally friendly in term of low reaction times and high yields.

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A study on the effect of spirocyclic structures in the main chain on the physical properties of copolyimides

Cited by 17 publications

References 18 publications

Synthesis of optically active alicyclic polyimides from a chiral, nonracemic dianhydride

Synthesis of optically active alicyclic polyimides from a chiral, nonracemic dianhydride

Advances in synthetic optically active condensation polymers - A review

Preparation and characterization of new inorganic–organic hybrid catalyst H₃PMo₁₂O₄₀/Hyd‐SBA‐15 and its application in the domino multi‐component reaction

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A study on the effect of spirocyclic structures in the main chain on the physical properties of copolyimides

Cited by 17 publications

References 18 publications

Synthesis of optically active alicyclic polyimides from a chiral, nonracemic dianhydride

Synthesis of optically active alicyclic polyimides from a chiral, nonracemic dianhydride

Advances in synthetic optically active condensation polymers - A review

Preparation and characterization of new inorganic–organic hybrid catalyst H3PMo12O40/Hyd‐SBA‐15 and its application in the domino multi‐component reaction

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Preparation and characterization of new inorganic–organic hybrid catalyst H₃PMo₁₂O₄₀/Hyd‐SBA‐15 and its application in the domino multi‐component reaction