Synthesis of racemic and optically active glycidic ethers, precursors of liquid crystalline polyethers

Taton, Daniel; Borgne, Alain Le; Chen, Jian; Shum, W.

doi:10.1002/(sici)1520-636x(1998)10:9<779::aid-chir1>3.0.co;2-b

Cited by 12 publications

(16 citation statements)

References 21 publications

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“…More recently, several authors have reported a set of racemic and chiral glycidylic compounds leading to polymers with 4‐cyanobiphenyl and 4‐alkoxybiphenyl mesogenic groups 20–22. These monomers were polymerized by using cationic (BF 3 ·Et 2 O),20 anionic (CsOH and t ‐BuOK/DMSO),23, 24 and ionic coordinative (Et 3 Al/AcAc/H 2 O)24 initiators.…”

Section: Introductionmentioning

confidence: 99%

“…The low‐molecular‐weight materials obtained show nematic, smectic, or cholesteric mesophases, but again, polymerization with (Et 3 Al/AcAc/H 2 O) failed to yield soluble materials because of the high molecular weight and tacticity of the samples. Undoubtedly, the major contribution by Taton et al22 was their observation of a transfer of chirality from the chiral centers in the main chain toward the mesophase in polymers with short spacers. This phenomenon was fully investigated by Spassky et al,25 by tailoring different copolymers.…”

Section: Introductionmentioning

confidence: 99%

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Studies on the modification of poly(ω‐bromoalkyl‐1‐glycidylether)s with 4′‐methoxybiphenyl‐4‐oxy mesogenic groups

Montornés¹,

Reina²,

Ronda³

2005

J. Polym. Sci. A Polym. Chem.

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A series of poly[ω‐(4′‐methoxy‐biphenyl‐4‐oxy)alkyl‐1‐glycidylether]s were synthesized by chemically modifying the corresponding poly(ω‐bromoalkyl‐1‐glycidylether)s with the sodium salt of 4‐hydroxy‐4′‐methoxybiphenyl. New high‐molecular‐weight side‐chain liquid‐crystalline polymers were obtained with excellent yields and almost quantitative degrees of modification. They were all insoluble in THF and other common solvents. Characterization by 13C NMR confirmed that all the polymers had the expected structure. The liquid crystalline behavior of the polymers was analyzed by DSC and polarized optical microscopy, and mesophase assignments were confirmed by X‐ray diffraction studies. Polymers that had alkyl spacers with n = 2 and 4 were smectic C, those that had spacers with n = 6 and 8 were nematic cybotactic, and those that had longer spacers (n = 10 and 12) were smectic C again. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 5998–6006, 2005

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Studies on the modification of poly(ω‐bromoalkyl‐1‐glycidylether)s with 4′‐methoxybiphenyl‐4‐oxy mesogenic groups

Montornés¹,

Reina²,

Ronda³

2005

J. Polym. Sci. A Polym. Chem.

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“…There is considerable interest in polymers consisting of aromatic units linked together directly or via ester, ketone, ether, thioether, sulfone, amide or imide moieties because they often form the basis of excellent high performance materials. In many cases these polymers also display liquid crystal properties [11]. It can, 2 however, encounter processing difficulties due to their high glass transition or melting temperatures coupled with insolubility in most organic solvents.…”

Section: Introductionmentioning

confidence: 99%

Preparation and characterization of new thermally stable and optically active polyesters by direct polycondensation reaction promoted by Vilsmeier adduct

Mallakpour

Tirgir

2009

E-Polymers

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Abstract:Highly soluble and optically active aromatic polyesters (PE)s containing phthalimide and flexible chiral groups were prepared with moderate molecular weights by step-growth polymerization of diacid monomer containing pendant 4-[(2L)-phthalimidylpropanoylamino)benzoyl group with several aromatic diols, in a system of tosyl chloride, pyridine (Py) and N,N-dimethylformamide (DMF) to give a series of new optically active PEs with good yield and moderate inherent viscosity ranging from 0.28 to 0.48 dL/g. The aim of this work was to obtain novel optically active PEs that was more soluble in common organic solvents while maintaining the high thermal stability. All polymers derived from such a diacid and aromatic diols were highly organosoluble in solvents like N-methyl-2-pyrrolidinone, N,Ndimethylacetamide, DMF, Py, dimethyl sulfoxide. Thermogravimetric analysis data showed that these PEs are thermally stable, with 10% weight loss being recorded above 400 °C and showed good thermal stability associated with high glasstransition temperatures above 200 °C as measured by differential scanning calorimetry. All of the above polymers were characterized by FT-IR and specific rotation techniques and some of them were also characterized by 1 H-NMR and elemental analyses methods.

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“…Examples of these promising materials are liquid-crystalline and non-linear optic polymers. [1] These materials can be molecularly designed by modifying polyethers with halogenated side groups. [2][3][4][5][6][7][8] We have already modified poly-(epichlorohydrin) (PECH) to a large extent with several nucleophiles, but in most cases there were undesirable side reactions such as crosslinking and chain cleavage.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Reactive Polyethers: Poly(-bromoalkyl-1-glycidylether)s

Montornés¹,

Reina²,

Ronda³

2001

Macromol. Chem. Phys.

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Synthesis of racemic and optically active glycidic ethers, precursors of liquid crystalline polyethers

Cited by 12 publications

References 21 publications

Studies on the modification of poly(ω‐bromoalkyl‐1‐glycidylether)s with 4′‐methoxybiphenyl‐4‐oxy mesogenic groups

Studies on the modification of poly(ω‐bromoalkyl‐1‐glycidylether)s with 4′‐methoxybiphenyl‐4‐oxy mesogenic groups

Preparation and characterization of new thermally stable and optically active polyesters by direct polycondensation reaction promoted by Vilsmeier adduct

Synthesis of New Reactive Polyethers: Poly(-bromoalkyl-1-glycidylether)s

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