Effect of phosphine ligand on the optical absorption/emission properties of platinum-containing conjugated polymers

Yu, Miao; Sotani, Taichi; Yajima, Tatsuo; Sano, Natsuhiro

doi:10.1039/c7py01886j

Cited by 15 publications

(10 citation statements)

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“…Poly( 1 ) was synthesized by the Sonogashira–Hagihara coupling polymerization of the corresponding iodophenyl‐ and ethynylphenyl‐substituted monomer 1 according to Scheme . Poly( 1 ) was obtained quantitatively irrespective of catalyst amount, while the M n increased from 1400 to 9800 as decreasing the catalyst amount accompanying the increase of Đ from 3.4 to 5.9 as listed in runs 1–3 in Table .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and crosslinking reaction of a novel polymer containing benzoxazine and phenyleneethynylene moieties in the main chain

Kobayashi

Goto

Miyamoto

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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A novel polymer, poly(1) containing benzoxazine and phenyleneethynylene moieties in the main chain with number‐average molecular weights ranging from 1400 to 9800 was obtained quantitatively by the Sonogashira–Hagihara coupling polymerization of the corresponding iodophenyl‐ and ethynylphenyl‐substituted monomer 1. Poly(1) was heated at 200 °C under N2 for 2 h to obtain the cured polymer, poly(1)′ via the ring‐opening polymerization of the benzoxazine moieties. The structures of the polymer before and after curing were confirmed by 1H‐NMR, IR, and UV–vis absorption and reflectance spectroscopies. Poly(1)′ was thermally more stable than monomer 1 and poly(1). A specimen was prepared from a mixture of poly(1) and phenol‐diaminodiphenylmethane type benzoxazine 2 by heating at 200 °C for 2 h under N2. The poly(1)/2 resin was thermally stable than bisphenol‐A type benzoxazine resin 3. Poly(1) exhibited XRD peaks corresponding to the d‐spacings of 1.26–0.98 and 0.40 nm, assignable to the repeating monomer unit and alignment of polymer molecules, respectively. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 2581–2589

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Section: Resultsmentioning

confidence: 99%

Synthesis and crosslinking reaction of a novel polymer containing benzoxazine and phenyleneethynylene moieties in the main chain

Kobayashi

Goto

Miyamoto

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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“…Fratoddi and co-workers synthesized platinum- and palladium-containing helical polyynes with 2,6-diethynyl-4-nitroaniline spacers . Our group synthesized various platinum-containing photoluminescent poly(aryleneethynylene)s, whose conjugation length and emission wavelength were controlled by arylene units and phosphine ligands . We also synthesized platinum-containing poly(aryleneethynylene)s with regulated secondary structures, wherein the aggregated and folded structures were controlled by substituents, solvent, and temperature. − …”

Section: Introductionmentioning

confidence: 99%

“…17 Our group synthesized various platinum-containing photoluminescent poly-(aryleneethynylene)s, whose conjugation length and emission wavelength were controlled by arylene units 18 and phosphine ligands. 19 We also synthesized platinum-containing poly-(aryleneethynylene)s with regulated secondary structures, wherein the aggregated and folded structures were controlled by substituents, solvent, and temperature. 19 acetylide complexes are readily exchanged with various bidentate phosphine ligands.…”

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Control of Higher-Order Structures of Platinum-Containing Conjugated Polymers by Ligand Exchange Reactions: Chirality Transfer from Optically Active Ligands to Optically Inactive Polymers

et al. 2021

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This study reports chirality transfer from optically active diphosphine ligands to optically inactive platinum-containing polymers. Cis-platinum complex 1 smoothly reacted with optically active diphosphine ligands L1 and L2 to give cis-platinum complex 1-L1 and trans dimeric platinum complex 1-L2, respectively. Cyclic trans dimeric complex 1-L2 gradually isomerized to cismonomeric complex 1-L2′. Polymer 4-L2 was insoluble in common organic solvents, even though the reaction was carried out under highly dilute conditions (c = 0.1 mM). On the other hand, polymer 5-L2 was CH 2 Cl 2 -soluble when the reaction was carried out at 1 and 0.1 mM concentrations, in which intramolecular bridging predominated over intermolecular crosslinking. CD spectroscopic measurements suggested that 5-L2 adopts a folded helical conformation, which was supported by DFT calculations.

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“…Chirality is a major concern in the modern pharmaceutical industry, pesticides, flavors, food additives, nonlinear optical materials, and asymmetric reactions and catalysis . Therefore, chiral recognition/resolution is of great interest and accordingly, large efforts have been paid to the techniques suitable for this aim, for example, chromatography, membrane separation, enzyme resolution, and chemical recognition .…”

Section: Introductionmentioning

confidence: 99%

Chiral phosphoric triamide‐based polymers for enantioseparation

Ahmadabad

Pourayoubi

Bakhshi

2019

J of Applied Polymer Sci

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Novel optical isomers of phosphoramide-methacrylate monomers were synthesized and used for the preparation of corresponding polymers and hydrogels as chiral absorbents. In order to direct enantioseparation, two simple and inexpensive methods were designed: (a) immobilization of the chiral polymers on glass beads as packing material for the separation columns and (b) filling of chiral hydrogels in tea bags to fabricate separation bags. The specific rotations for R-and S-monomers were + 22.0 and − 21.8 , while those for R-and S-polymers were + 20.8 and − 22.1 , respectively. The enantioseparation of (AE)-α-methylbenzylamine, DL-alanine, DL-valine, DL-tartaric acid, DL-phenylalanine, and omeprazole was evaluated. The maximum enantioseparation (optical purity) of 97% was observed for (AE)-α-methylbenzylamine by S-hydrogel. Chiral hydrogels resulted in enantioseparations with higher purities (up to 97%) comparing to the chiral polymers, but in longer times (2-3 days). The desorption process easily occurred from the absorbed columns or bags.Phosphoramides with a P( O)(N) segment are attractive to study owing to their extensive applications in the coordination chemistry, catalysts, and medicine. [32][33][34] From our previous studies on phosphorus-oxygen, phosphorus-nitrogen, and phosphorus-sulfur compounds, 35-37 the P O group was found as the best hydrogen-bond acceptor with respect to the other possible acceptor groups, which usually exist in the molecules, typically C O, S O, N─O, P S, ester and ether oxygen atoms, nitrogen, and π-system, examined with X-ray diffraction study, statistical analysis based on the data deposited in the Cambridge structural database (CSD) 38 and quantum chemical calculations in some cases. The structures investigated include achiral, racemate, and chiral single-enantiomer phosphorus compounds. 36,37,39,40 According to Reaxys web-based tool (licensed by Elsevier) for chiral polymers, there is no report about an enantiomeric pair of phosphoric triamide-based polymers, and such polymers seem to be good chiral selectors, due to relatively strong interaction of P O with OH and NH units, as was observed in small molecules model compounds.In this work, levo-and dextro-rotatory isomers with two chiral centers, P( O)(NH-R-(−)CH(CH 3 )C 6 H 5 ) 2 (Cl) and P( O)(NH-S-(−)CH(CH 3 )C 6 H 5 ) 2 (Cl) (1 and 2), have been synthesized and reacted with 2-aminoethylmethacrylate (AEMA) to prepare phosphoric triamides monomers (3 and 4) as chiral selectors. The methacrylate moiety brought the opportunity for the radical or ionic polymerization reactions of these monomers. Through radical polymerization of these novel monomers, a pair of singleenantiomer phosphoric triamide-based polymers (P1 and P2) and hydrogels (H1 and H2) were prepared. In order to direct Additional Supporting Information may be found in the online version of this article.

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Effect of phosphine ligand on the optical absorption/emission properties of platinum-containing conjugated polymers

Abstract: The λmax values of platinum-containing poly(phenyleneethynylene)s with aryl groups bonded to P were higher than those with alkyl groups.

Cited by 15 publications

References 20 publications

Synthesis and crosslinking reaction of a novel polymer containing benzoxazine and phenyleneethynylene moieties in the main chain

Synthesis and crosslinking reaction of a novel polymer containing benzoxazine and phenyleneethynylene moieties in the main chain

Control of Higher-Order Structures of Platinum-Containing Conjugated Polymers by Ligand Exchange Reactions: Chirality Transfer from Optically Active Ligands to Optically Inactive Polymers

Chiral phosphoric triamide‐based polymers for enantioseparation

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