Synthesis of optically active green fluorescent π-conjugated fluorenepolymers having chiral Schiff bases in the side chain

Asai, Kengo; Konishi, Gen‐ichi; Sumi, Kentaro; Kawauchi, Susumu

doi:10.1039/b9py00268e

Cited by 18 publications

(11 citation statements)

References 46 publications

(11 reference statements)

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“…The fact that BPPEs possess a very large number of unreacted Ph‐CH 2 Br groups26–35 is of particular interest in the study of functional polymers. To confirm whether 6 can be made functional, we carried out a simple polymerization reaction and attempted to improve the thermal stability and processability of the obtained polymer.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of a branched poly(phenylene ethylene) with bromomethyl groups as an organosoluble and functional parylene

Kobayashi

Sumi

Konishi

2011

J of Applied Polymer Sci

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We synthesized a branched poly(phenylene ethylene) (BPPE) with bromomethyl groups from 1,3,5-tris(bromomethyl)benzene derivatives via the Wurtz coupling reaction. In the case of 1,3,5-tris(bromomethyl)-2,4,6-trimethoxybenzene as a monomer, the obtained polymer (M n ¼ 6100, M w /M n ¼ 1.9) had bromomethyl groups. The 1 HNMR analysis showed that a very large number of unreacted bromomethyl groups (Ph-CH 2 Br) remained in the BPPE; the reaction of this polymer with phenolic hydroxyl groups proceeded quantitatively. This suggested that BPPEs can be functionalized using unreacted bromomethyl groups, making them a very attractive starting point for the creation of functionalized BPPEs with further enhanced processability.

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Section: Resultsmentioning

confidence: 99%

Synthesis of a branched poly(phenylene ethylene) with bromomethyl groups as an organosoluble and functional parylene

Kobayashi

Sumi

Konishi

2011

J of Applied Polymer Sci

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“…In this study, we prepared high refractive index polystyrenes possessing a thiophene moiety by the Suzuki‐Miyaura coupling reaction50–55 of poly (styrene‐ co ‐4‐bromostyrene). It is noted that this polymer reaction strategy presents a simple and strong tool for the design of high refractive index polystyrene.…”

Section: Introductionmentioning

confidence: 99%

Facile synthesis of high refractive index thiophene‐containing polystyrenes

Konishi

2011

J of Applied Polymer Sci

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High refractive index polymer films have been extensively investigated because of their wide application potentials. We now designed thiophene-containing polystyrene as colorless and transparent high-refractiveindex thin film. The copolystyrenes were synthesized by general radical polymerization with controlled mole ratios 0 : 10, 1 : 9, 3 : 7, 5 : 5, 7 : 3, 9 : 1, 10 : 0 (styrene : p-bromostyrene), respectively. Next, the thiophene-containing polystyrenes were synthesized by Suzuki-Miyaura coupling reaction. The chemical structures of synthesized thiophene-containing polystyrene in accordance with ratios were confirmed by using 1 H-NMR, 13C-NMR, and FTIR. The effect of the thiophene units on refractive index according to copolymer ratios were confirmed by using prism coupler. The thiophene-containing polystyrene showed improved refractive index ranging from 1.58 to 1.67 and birefringence in the range of 0.0001-0.0019. The thermal stability and thermal behaviors of thiophene-containing polystyrene also can be confirmed by TGA and DSC. The polymers have high glass transition temperature in the range of 108 C-177 C.

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“…GPC analysis of this Figure 24. Synthesis of optically active polyfluorenes with chiral Schiff bases in the side chain by the palla-dium-catalyzed Suzuki-Miyaura coupling polymerization [258] polymer showed M W = 41 000 and M n = 20 000. The specific optical rotation of resulting polymer was -289.4°.…”

Section: Synthesis Of Optically Active Polymers By Suzuki-miyaura Coumentioning

confidence: 99%

“…They utilized this polymer in a tandem catalytic asymmetric diethylzinc addition and asymmetric hydrogenation of p-acetylbenzaldehyde to generate a chiral diol. The synthesis of optically active poly(fluorene-altchiral iminofluorene)s using 1-phenylethylamine as a chiral auxiliary was described by Asai et al [258]. Optically active polyfluorenes were synthesized by the palladium-catalyzed Suzuki-Miyaura coupling polymerization of 9,9!-dioctylfluorene-2,7-bis(trimethyleneborate) with a chiral Schiff base monomer (imino group modified-fluorene) (Figure 24).…”

Section: Synthesis Of Optically Active Polymers By Suzuki-miyaura Coumentioning

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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Synthesis of optically active green fluorescent π-conjugated fluorenepolymers having chiral Schiff bases in the side chain

Cited by 18 publications

References 46 publications

Synthesis of a branched poly(phenylene ethylene) with bromomethyl groups as an organosoluble and functional parylene

Synthesis of a branched poly(phenylene ethylene) with bromomethyl groups as an organosoluble and functional parylene

Facile synthesis of high refractive index thiophene‐containing polystyrenes

Advances in synthetic optically active condensation polymers - A review

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