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PubMed1995

Hydrophilization of porous polystyrene-based continuous rod column.

Reactive porous rods of poly[(chloromethyl)styrene-co-divinylbenzene] have been prepared for the first time by copolymerization of the monomers in the presence of a porogenic diluent. A two-step modification process involving reaction with ethylenediamine followed by reaction with gamma-gluconolactone leads to a porous medium that has highly hydrophilic surface functionalities. Preliminary chromatographic evaluation with both small molecules such as alkylbenzenes in reversed-phase mode and large proteins in hydrophobic adsorption and ion-exchange modes demonstrates that the surface of the modified rods possesses a hydrophilicity that is comparable to that of the best hydrophilic HPLC packings.

Chromatography, High Pressure Liquid↗
PubMedDate not supplied

Deazapurine solid-phase synthesis: combinatorial synthesis of a library of N3,N5,C6-trisubstituted pyrrolo[3,2-d]pyrimidine derivatives on cross-linked polystyrene bearing a cysteamine linker.

Solid-phase methodology for the preparation of pyrrolo[3,2-d]pyrimidine-6-carboxylates with diversity at the N3 pyrmidine nitrogen has now been elaborated to allow for the generation of pyrrolopyrimidine libraries with members possessing diversity at the N3, N5, and C6 positions. The diversification of the N5 position was achieved by treating the parent resin-bound pyrrolo[3,2-d]pyrimidines 3 with an alkyl halide in the presence of Cs2CO3 in DMF. Modification of the C6 carboxylate of resin-bound pyrrolopyrimidines 3-5 was first achieved by hydrolysis of the benzyl ester using LiOH in a mixture of THF/H2O/MeOH. Further alteration of the C6 position of resin-bound pyrrolo[3,2-d]pyrimidine-6-carboxylic acids 6-8 was then performed by activation with triphosgene and treatment with an amine to furnish resin-bound pyrrolo[3,2-d]pyrimidine-6-amides. Twenty-two pyrrolo[3,2-d]pyrimidines 1a-v with different substituents at the N3, N5, and C6 positions were obtained in yields of 21-83% and purities of 61-98% after cleavage from the solid support.

Journal Article↗
PubMed2003

Preparation and pH triggered inversion of vesicles from poly(acrylic acid)-block-polystyrene-block-poly(4-vinyl pyridine).

The aggregate morphologies of the biamphiphilic triblock PAA(26)-b-PS(890)-b-P4VP(40) have been studied by TEM as a function of pH in DMF/THF/H(2)O mixtures. The outside surfaces of the aggregates were characterized by zeta potential measurements. Starting at the apparent pH (pH) of 1, and increasing gradually to pH14, the aggregate morphologies of this triblock change progressively from vesicles (pH1), to solid spherical or ellipsoidal aggregates (pH3 approximately 11), and finally back to vesicles (pH14). Vesicles prepared at pH1 contain P4VP chains on the outside and PAA chains on the inside, while those prepared from the same triblock at pH14 contain PAA outside and P4VP inside. The segregation is based on the difference in repulsive interactions within the PAA or P4VP corona under different pH conditions. At low pH, the curvature is stabilized through increased repulsive interactions between the P4VP chains on the outside relative to the less repulsive interactions between the PAA chains on the inside. At pH14, by contrast, the PAA is preferentially segregated to the outside and the P4VP to the inside because of the increased repulsive interaction between PAA chains and the decreased repulsive interaction between P4VP chains at high pH. Most importantly, vesicles with PAA on the outside can be inverted to P4VP on the outside by changing the pH while the vesicles have swollen cores and are under dynamic conditions. The conversion mechanism is suggested to involve a whole vesicle process because the CMC is far too low for single chain reassembly to be involved.

Journal Article↗
PubMed2005

Polystyrene-supported (R)-2-piperazino-1,1,2-triphenylethanol: a readily available supported ligand with unparalleled catalytic activity and enantioselectivity.

A very active and highly enantioselective catalytic resin, designed for minimal perturbation of the catalytic center by the polymer matrix, has been assembled in two steps from (S)-triphenylethylene oxide, piperazine, and Merrifield resin and tested in the enantioselective ethylation of aldehydes. 1-Arylpropanols of 94-95% ee are obtained in high yield by the use of only 2 mol % of catalytic resin at 0 degrees C for 4 h.

Journal Article↗
PubMed1998

High Catalytic Activity of Chiral Amino Alcohol Ligands Anchored to Polystyrene Resins.

Enantiomerically pure (2S,3S)-2,3-epoxy-3-phenylpropanol (3) has been anchored to Merrifield resins with different degrees of cross-linking and functionalization. The resulting epoxy-functionalized resins 4 have been submitted to completely regioselective (C-3 attack) and stereospecific ring-opening with secondary amines [piperidine (a), N-methylpiperazine (b), and cis-2,6-dimethylpiperidine (c)] in the presence of lithium perchlorate to afford (2R,3R)-3-(dialkylamino)-2-hydroxy-3-phenylpropoxy resin ethers 5a-c. The progress of these two processes has been monitored by (13)C gel-phase NMR spectroscopy. Polymer-supported amino alcohols 5a-c have been evaluated as catalytic ligands in the enantioselective addition of diethylzinc to benzaldehyde, best results being obtained with the cis-2,6-dimethylpiperidine containing ligand 5c. Analogously, (2R,3R)-3-(cis-2,6-dimethylpiperidino)-3-phenyl-1,2-propanediol (11) has been anchored to a 2-chlorotrityl chloride resin (Barlos resin) in dichloromethane in the presence of diisopropylethylamine, and the anchoring process has been also monitored by (13)C gel-phase NMR spectroscopy. The resulting resin 12 has subsequently been used as a chiral ligand in the catalytic addition at 0 degrees C of diethylzinc to a family of fourteen representative aromatic and aliphatic aldehydes 8a-n, to afford the corresponding (S)-1-substituted 1-propanols 10a-n with a mean enantiomeric excess of 92%.

Journal Article↗
PubMed2006

Catalyzed radical polymerization of styrene vapor on nanoparticle surfaces and the incorporation of metal and metal oxide nanoparticles within polystyrene polymers.

We present a novel approach to polymerize olefin vapors on the surfaces of metallic and semiconductor nanoparticles. In this approach, a free radical initiator such as AIBN is dissolved in a volatile solvent such as acetone. Selected nanoparticles (prepared separately using the laser vaporization-controlled condensation method) are used to form initiator-coated nanoparticles placed on a glass substrate. The olefin (styrene) vapor is polymerized by the thermally activated initiator on the nanoparticle surfaces. Our approach also provides structural and mechanistic information on the early stages of catalyzed gas-phase polymerization, which can be used to correlate the gas-phase structural properties with the bulk properties and the performance of the polymer nanocomposites. This correlation is the key step in controlling the properties of the polymer nanocomposites. Our results clearly demonstrate the success of this method in preparing polymer coated nanoparticles for a variety of interesting applications. The precise control of the chemical functionality, thickness, and morphology of the polymer film and the size, size distribution, and properties of the core nanoparticles (photoluminescence, magnetic) may lead to major technological breakthroughs in a variety of applications including drug delivery, ultrasensitive detectors, and chemical and biological sensors.

Letter↗