Synthesis and properties of helical aliphatic polyacetylene containing a cholesteryl group in the side chain

Mitsuyama, Masahiro; Kondo, Koichi

doi:10.1002/1521-3935(20000901)201:14<1613::aid-macp1613>3.0.co;2-n

Cited by 22 publications

(12 citation statements)

References 6 publications

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“…Although the results obtained from WCl 6 –Ph 4 Sn are poor, we do not give up. Since complexes of late transition metals such as Rh are known to be more tolerant of functional groups,35, 76–90 we tried to polymerize the monomer by [Rh(nbd)Cl] 2 . Stirring 1 (8) in THF/Et 3 N with a catalytic amount of [Rh(nbd)Cl] 2 at room temperature for 24 h, delightfully, produces a brown solid in 70% yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and liquid crystalline properties of poly(1‐alkyne)s carrying triphenylene discogens

Xing

Lam

Zhao

et al. 2008

J. Polym. Sci. A Polym. Chem.

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Triphenylene-containing 1-decynes with different alkyl chain lengths and their polymers are synthesized and the effects of the structural variables on their mesomorphic properties are investigated. The monomers [HCϵC(CH 2 ) 8 CO 2 C 18 H 6 (OC m H 2mþ1 ) 5 ; m ¼ 4-9] are prepared by consecutive etherization, coupling, and esterification reactions. The monomers form columnar phases at room temperature. The polymerizations of the monomers are effected by [Rh(nbd)Cl] 2 , producing soluble polymers in high yields (up to 84%). The structures and properties of the polymers are characterized and evaluated by IR, NMR, TGA, DSC, POM, and XRD analyses. All the polymers are thermally stable, losing little of their weights when heated to 300 8C. The isotropization temperature of the polymers increases initially with the length of alkyl chain but decreases on further extension. Although the polymers with shorter and longer alkyl chain lengths adopt a homogeneous hexagonal columnar structure, those with intermediate ones form mesophases with mixed structures.

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Section: Resultsmentioning

confidence: 99%

Synthesis and liquid crystalline properties of poly(1‐alkyne)s carrying triphenylene discogens

Xing

Lam

Zhao

et al. 2008

J. Polym. Sci. A Polym. Chem.

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“…Cholesteryl group can be considered a promising functional group present in molecules, which could be applied to optical lters for high-power laser systems, 42 rewritable memories and also recording media. 43 Thus, the crystal structures of cholesteryl-butyl carbonate and cholesteryl-oleyl carbonate are being investigated for liquid crystals applications.…”

Section: Converted Carbonates (Mmol) Smentioning

confidence: 99%

Cycling of waste fusel alcohols from sugar cane industries using supercritical carbon dioxide

Pereira

Crédito

et al. 2015

RSC Adv.

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The present study describes the clean synthesis of non-phosgene organic carbonates (NPOCs) from a selective multicomponent reaction with two important by-products from sugar and alcohol industries, namely, fusel alcohols and carbon dioxide, in the presence of 1,8-diazabicycloundecene (DBU), 1,5-diazabicyclo[4.3.0]-non-5-ene (DBN) or 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]-pyrimidine (TBD) and an alkylating agent. The bases were used for the nucleophilic activation of the alcohols. The synthesis of carbonates was carried out without solvent and confirmed by GC-MS with EI ionization mode, 1 H-and 13 C-NMR and FT-IR analysis. The carbonates were obtained in excellent yields. Crude fusel alcohol can be converted to alkylcarbonates. The proposed methodology can also be employed to convert other hydroxylated compounds into carbonates.

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“…3). These exothermic peaks were thought to come from thermal isomerization from cis to trans structure because the main chain of the homopolymers was mainly composed of the stereoregular cis–transoidal structure,7, 8 and such an exothermic reaction is not observed for trans‐rich polyacetylenes 9. Obviously, these results suggest that the stereoregularity of the obtained copolymers would be mainly composed of the cis‐type structure.…”

Section: Resultsmentioning

confidence: 90%

“…Rh(nbd)[B(C 6 H 5 ) 4 ] was prepared by the reaction of [Rh(nbd)Cl] 2 and NaB(C 6 H 5 ) 4 , as described in the literature 6(f) . 1 and 2 were synthesized according to procedures previously reported 7, 8…”

Section: Methodsmentioning

confidence: 99%

“…The reason is that air‐stable, stereoregular cis–transoidal polymers are easily yielded from phenylacetylenes with Rh catalysts, and the stereoregular cis conformation is suitable for inducing a one‐handed helical conformation, whereas poly(aliphatic acetylenes) are unstable in air, leading to a decrease in the molecular weight due to oxidative main‐chain scission and conformation out of control 7. Recently, we reported that the polymerization of cholesteryl 3‐butynyl carbonate ( 2 ) with a Rh(nbd)[B(C 6 H 5 ) 4 ] (nbd = norbornadiene) catalyst gave an air‐stable, stereoregular cis‐type polymer with an one‐handed helical conformation in the main chain 8…”

Section: Introductionmentioning

confidence: 99%

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Induced chiral helical effect on the main chain of aliphatic polyacetylenes

Mitsuyama

Kondo

2001

J. Polym. Sci. A Polym. Chem.

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11‐Dodecyn‐1‐ol as an achiral, aliphatic, monosubstituted acetylene was copolymerized with cholesteryl 3‐butynyl carbonate as a chiral, aliphatic, monosubstituted acetylene with Rh(nbd)[B(C6H5)4] (nbd = norbornadiene) in tetrahydrofuran. The main chain of the obtained copolymers seemed to be mainly composed of the cis‐type structure. The backbone π–π* transition of these copolymers showed significant circular dichroism (CD), indicating an excess of one‐handed helical conformation. These CD signals were varied with the contents of the cholesteryl units in the copolymers. © 2001 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 39: 913–917, 2001

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Synthesis and properties of helical aliphatic polyacetylene containing a cholesteryl group in the side chain

Cited by 22 publications

References 6 publications

Synthesis and liquid crystalline properties of poly(1‐alkyne)s carrying triphenylene discogens

Synthesis and liquid crystalline properties of poly(1‐alkyne)s carrying triphenylene discogens

Cycling of waste fusel alcohols from sugar cane industries using supercritical carbon dioxide

Induced chiral helical effect on the main chain of aliphatic polyacetylenes

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