Metal‐induced supramolecular chirality in optically active polymers of oxazoline‐substituted <i>N</i>‐phenylmaleimides

Xi, Xiujuan; Jiang, Liming; Sun, Wen‐Hua

doi:10.1002/chir.20369

Cited by 16 publications

(8 citation statements)

References 37 publications

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“…Xi et al50 reported the formation of optically active N ‐substituted maleimide polymers bearing oxazoline groups as pendant and copper (II) ion complexes. They demonstrated the formation of chiral supramolecular aggregate of N ‐substituted maleimide polymers–copper (II) ion complexes by specific rotations, CD, and AFM measurements.…”

Section: Resultsmentioning

confidence: 99%

Asymmetric polymerizations of chiral 4‐benzyl‐2‐ethynyloxazoline with rhodium catalyst and chiroptical properties of the polymers

et al. 2011

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Optically active 4-alkyl-2-ethynyloxazoline derivatives (BnEOx) were polymerized with rhodium catalysts. The polymerization in toluene produced polymer with the highest absolute values of specific rotation ([α](D) = -77.3°). The yields, molecular weights, and specific rotations of poly(BnEOx)s were influenced by polymerization conditions. The copolymerization with phenylacetylene (PA) was effective to increase the molecular weight of the copolymer. It is interesting to note that the copolymers exhibited positive specific rotations ([α](D) = +4.7° to +62.5°) despite the fact that [α](D) s of BnEOx and the homopolymer are negative sign. The chiroptical properties were investigated by the chiral/achiral copolymerization of BnEOx with PA. The copolymerizations of BnEOx with PA gave copolymers containing higher order structure such as one-handed helical conformation. Furthermore, induced Cotton effects were observed in the π-π* transition region of conjugated main chain depending a complex of these polymers with zinc triflate salt in tetrahydrofuran solution, indicating the formation of chiral supramolecular aggregates.

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Section: Resultsmentioning

confidence: 99%

Asymmetric polymerizations of chiral 4‐benzyl‐2‐ethynyloxazoline with rhodium catalyst and chiroptical properties of the polymers

et al. 2011

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“…17 Chiral oxazolinemetal complexes are a versatile type of catalyst and have been used in several asymmetric reactions, including Diels-Alder, aldol, aziridination, allylic alkylation and cyclopropanation reactions. 18 Jiang et al [19][20][21] synthesized a series of optically active polymers containing chiral oxazoline side chains. They found that the polymers bearing oxazoline groups as substituents tended to form chiral supramolecular aggregates upon the addition of metal ions.…”

Section: Introductionmentioning

confidence: 99%

“…They found that the polymers bearing oxazoline groups as substituents tended to form chiral supramolecular aggregates upon the addition of metal ions. 20 The polymer-metal complexes showed outstanding chiral recognition ability toward some substrates, as evidenced by changes in the fluorescence intensity. 19,21 Therefore, it is expected that the incorporation of chiral oxazoline derivatives into the polymer main chain will lead to the development of new types of functional polymers, such as polymeric catalysts.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of optically active poly(phenylene-ethynylene)s containing chiral oxazoline derivatives

Rattanatraicharoen

Yamabuki

Oishi

et al. 2011

Polym J

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Novel optically active (S)-2-(3,5-diiodophenyl)oxazoline derivatives ((S)-DIPhROx)) (R¼4-benzyl (1a), 4-phenyl (1b)) were synthesized and polymerized using the Sonogashira-Hagihara coupling reaction to obtain the poly(phenylene-ethynylene)s bearing oxazoline derivatives in the weight range from 1060 to 17 300 in 40-72% yields. The polymers were thermally stable up to 220 1C. All the polymers exhibited higher specific rotation values than the model compound did. Moreover, these polymers also showed intense circular dichroism (CD) signals in the transition region of the conjugated main chain, whereas almost no induced Cotton effect was observed for the model compound. The results of the specific rotation and CD and ultraviolet analyses indicate that the optical activities of the polymers arise not only from the configurational chirality of the optically active oxazoline pendant groups but also from elements of higher-order structure such as the helical conformation.

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“…[28][29][30][31] We previously reported a new type of optically active polymer based on N-phenylmaleimideand Nphenylmethacrylamide derivatives, in which a chiral oxazoline lateral group was connected to the backbone through the benzene ring. [32][33][34][35][36][37][38] It was demonstrated that the maleimide-type polymers and their metal-complexes had a moderate enantioselectivity in fluorescent response toward some chiral compounds. 39 More recently, we found that polyacrylamides bearing a chiral oxazoline pendant presented a favorable chiral recognition ability, as evidenced by 1 H-NMR study, where the characteristic signal of the hydroxyl group in 1,1 0 -bi-2-naphthol (BINOL) was split into two peaks, ascribed, respectively, to the levo and dextro isomers due to the asymmetric induction of the polymer.…”

Section: Introductionmentioning

confidence: 99%

“…We previously reported a new type of optically active polymer based on N ‐phenylmaleimide‐ and N ‐phenylmethacrylamide derivatives, in which a chiral oxazoline lateral group was connected to the backbone through the benzene ring 32–38. It was demonstrated that the maleimide‐type polymers and their metal‐complexes had a moderate enantioselectivity in fluorescent response toward some chiral compounds 39.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of macroporous silica modified with optically active poly[N‐(oxazolinylphenyl)acrylamide] derivatives for potential application as chiral stationary phases

Tian

Che

et al. 2009

J of Applied Polymer Sci

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Enantiopure acrylamide derivatives, (S)-N-[o-(4-methyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]acrylamide and (R)-N-[o-(4-phenyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]acrylamide, were synthesized through the acylation of chiral 2-oxazolinylanilines. The radical polymerization of the chiral monomers was carried out with (3-mercaptopropyl)trimethoxysilane as a chain-transfer agent to obtain the corresponding optically active prepolymers with a trimethoxysilyl group. By immobilizing the prepolymers on porous silica gel via the grafting-to method, we prepared a new chiral stationary phase (CSP) and characterized it by elemental analysis, thermogravimetry, and Fourier transform infrared spectroscopy. The enantioseparation capacities of the CSPs were evaluated with high-performance liquid chromatography toward several racemic compounds, including 1,1 0 -bi-2-naphthol, benzoin, 2-amino-1-butanol, and loxoprofen sodium under the normal-phase mode. The results indicate that the CSPs exhibited improved chromatographic performances compared to their brush-type analogs obtained by the alternative grafting-from approach. Also, the column packed with poly{(R)-N-[o-(4-phenyl-4,5-dihydro-1,3-oxazol-2-yl)phenyl]acrylamide}-bonded silica was found to have an extent of enantioselectivity in the chiral resolution of some unmodified amino acids with reversed-phase eluents.

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Metal‐induced supramolecular chirality in optically active polymers of oxazoline‐substituted N‐phenylmaleimides

Cited by 16 publications

References 37 publications

Asymmetric polymerizations of chiral 4‐benzyl‐2‐ethynyloxazoline with rhodium catalyst and chiroptical properties of the polymers

Asymmetric polymerizations of chiral 4‐benzyl‐2‐ethynyloxazoline with rhodium catalyst and chiroptical properties of the polymers

Synthesis and characterization of optically active poly(phenylene-ethynylene)s containing chiral oxazoline derivatives

Synthesis and characterization of macroporous silica modified with optically active poly[N‐(oxazolinylphenyl)acrylamide] derivatives for potential application as chiral stationary phases

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