Name: atom transfer radical polymerization of functionalized vinyl monomers using perylene as a visible light photocatalyst
Uploaded: 2016-04-22T13:00:00
Description: Watch this Scientific Journal Video about Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst at JoVE.com

The authors would like to acknowledge the University of Colorado Boulder for its support of this work.

PRECAUCIÓN: Muchas de las sustancias químicas utilizadas en este protocolo son sustancias peligrosas. Consulte las Hojas de Datos de Seguridad del Material (MSDS) y el uso de equipo de protección personal (EPP) apropiado cuando se trabaja con estas sustancias. 1. La purificación, la preparación y conservación de los reactivos <ol><li> Purificar todos los disolventes para ser utilizados con un sistema de purificación de disolvente de acuerdo con el protocolo del fabricante. Si un sis...

<ol>
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L. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=The+Convergence+of+Synthetic+Organic+and+Polymer+Chemistries.">The Convergence of Synthetic Organic and Polymer Chemistries.</a> Science. 309 (5738), 1200-1205 (2005).</li><li>di Lena, F., Matyjaszewski, K. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Transition+Metal+Catalysts+for+Controlled+Radical+Polymerization.">Transition Metal Catalysts for Controlled Radical Polymerization.</a> Prog. Polym. Sci. 35 (8), 959-1021 (2010).</li><li>Rosen, B. 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V. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Nanostructured+Functional+Materials+Prepared+by+Atom+Transfer+Radical+Polymerization.">Nanostructured Functional Materials Prepared by Atom Transfer Radical Polymerization.</a> Nat. Chem. 1 (4), 276-288 (2009).</li><li>Ouchi, M., Terashima, T., Sawamoto, M. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Precision+Control+of+Radical+Polymerization+via+Transition+Metal+Catalysis:+From+Dormant+Species+to+Designed+Catalysts+for+Precision+Functional+Polymers.">Precision Control of Radical Polymerization via Transition Metal Catalysis: From Dormant Species to Designed Catalysts for Precision Functional Polymers.</a> Acc. Chem. Res. 41 (9), 1120-1132 (2008).</li><li>Matyjaszewski, K., Xia, J. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Atom+Transfer+Radical+Polymerization.">Atom Transfer Radical Polymerization.</a> Chem. Rev. 101 (9), 2921-2990 (2001).</li><li>Magenau, A. J. D., Strandwitz, N. 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H. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Living+Radical+Polymerization+by+the+RAFT+Process-+A+Second+Update.">Living Radical Polymerization by the RAFT Process- A Second Update.</a> Aust. J. Chem. 62 (11), 1402-1472 (2009).</li><li>Moad, G., Rizzardo, E., Thang, S. H. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Radical+Addition-Fragmentation+Chemistry+in+Polymer+Synthesis.">Radical Addition-Fragmentation Chemistry in Polymer Synthesis.</a> Polymer. 49 (5), 1079-1131 (2008).</li><li>Nicolas, J., et al. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Nitroxide-Mediated+Polymerization.">Nitroxide-Mediated Polymerization.</a> Prog. Polym. Sci. 38 (1), 63-235 (2013).</li><li>Hawker, C. J., Bosman, A. W., Harth, E. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=New+Polymer+Synthesis+by+Nitroxide+Mediated+Living+Radical+Polymerizations.">New Polymer Synthesis by Nitroxide Mediated Living Radical Polymerizations.</a> Chem. Rev. 101 (12), 3661-3688 (2001).</li><li>Goto, A., Wakada, T., Fukuda, T., Tsujii, Y. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=A+Systematic+Kinetic+Study+in+Reversible+Chain+Transfer+Catalyzed+Polymerizations+(RTCPs)+with+Germanium,+Tin,+Phosphorus,+and+Nitrogen+Catalysts.">A Systematic Kinetic Study in Reversible Chain Transfer Catalyzed Polymerizations (RTCPs) with Germanium, Tin, Phosphorus, and Nitrogen Catalysts.</a> Macromol. Chem. Phys. 211 (5), 594-600 (2010).</li><li>Goto, A., Ohtsuki, A., Ohfuji, H., Tanishima, M., Kaji, H. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Reversible+Generation+of+a+Carbon-Centered+Radical+from+Alkyl+Iodide+Using+Organic+Salts+and+Their+Application+as+Organic+Catalysts+in+Living+Radical+Polymerization.">Reversible Generation of a Carbon-Centered Radical from Alkyl Iodide Using Organic Salts and Their Application as Organic Catalysts in Living Radical Polymerization.</a> J. Am. Chem. Soc. 135 (30), 11131-11139 (2013).</li><li>Goto, A., et al. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Reversible+Complexation+Mediated+Living+Radical+Polymerization+(RCMP)+Using+Organic+Catalysts.">Reversible Complexation Mediated Living Radical Polymerization (RCMP) Using Organic Catalysts.</a> Macromolecules. 44 (22), 8709-8715 (2011).</li><li>Miyake, G. M., Theriot, J. C. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Perylene+as+an+Organic+Photocatalyst+for+the+Radical+Polymerization+of+Functionalized+Vinyl+Monomers+Through+Oxidative+Quenching+With+Alkyl+Bromides+and+Visible+Light.">Perylene as an Organic Photocatalyst for the Radical Polymerization of Functionalized Vinyl Monomers Through Oxidative Quenching With Alkyl Bromides and Visible Light.</a> Macromolecules. 47 (23), 8255-8261 (2014).</li><li>Miyake, G. M. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Organocatalyzed+Photoredox+Mediated+Polymerization+Using+Visible+Light.">Organocatalyzed Photoredox Mediated Polymerization Using Visible Light.</a> US Patent Application. 14, (2013).</li><li>Treat, N. J., et al. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Metal-Free+Atom+Transfer+Radical+Polymerization.">Metal-Free Atom Transfer Radical Polymerization.</a> J. Am. Chem. Soc. 136 (45), 16096-16101 (2014).</li><li>Pan, X., Lamson, M., Yan, J., Matyjaszewski, K. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Photoinduced+Metal-Free+Atom+Transfer+Radical+Polymerization+of+Acrylonitrile.">Photoinduced Metal-Free Atom Transfer Radical Polymerization of Acrylonitrile.</a> ACS Macro Lett. 4 (2), 192-196 (2015).</li></ol>

Aunque el protocolo demuestra un ejemplo específico de esta técnica de polimerización, las opciones disponibles para el investigador que realizan esta reacción son bastante amplio. Las modificaciones se pueden hacer en una serie de puntos a lo largo del protocolo para permitir la optimización de cualquier photoredox particular, se está realizando ATRP. A medida que nuevos monómeros, iniciadores y catalizadores para esta reacción están siendo investigados, la estequiometría y el disolvente utilizado para llevar...

The synthesis of technologically advanced polymers requires precise control over polymer molecular weight, dispersity (&#208;), composition, and architecture.1,2 Controlled radical polymerizations (CRPs)3-8 have revolutionized the synthesis of well-defined polymers, with atom transfer radical polymerization (ATRP) being the most used CRP, largely due to operational simplicity and synthetic versatility.9-14 The crux of ATRP is the ability to reversibly deactivate the polymerization, controlling the equilibrium between a propagating radical and a dormant species. Enforcing a low concentration of active radicals greatly minimizes bimolecular termination pathways and allows for the synthesis of well-defined polymers. 
Traditional ATRP relies on a transition metal catalyst to mediate this equilibrium.3 These metal catalysts contaminate the polymer product and impede implementation in biomedical or electronic applications while also raising environmental concerns. Although significant strides have been made to reduce the catalyst concentration to ppm levels, these methodologies require more demanding experimental conditions and metal contamination is still not entirely eliminated.15,16
Reversible addition-fragmentation transfer17,18 and nitroxide-mediated polymerizations19,20 are CRPs that do not require metal catalysts, although they have been used less often than ATRP.3 Recently, reversible chain-transfer21 and reversible complexation22,23 variants of ATRP that can use organic catalysts were reported. However, these methodologies require the use of alkyl iodide initiators and are not effective with the alkyl bromides commonly employed in ATRP. A highly desirable CRP would match the performance, feasibility, and robustness of traditional ATRP while being catalyzed by an organic catalyst under mild conditions.
Here, we describe a methodology for the radical polymerization of functionalized vinyl monomers using perylene as a visible-light photocatalyst. Through optimization of parameters such as stoichiometry, concentration, time, and light flux, the molecular weight of the polymers can be controlled.24, 25 Similar methodologies have been recently introduced using phenothiazine derivatives as photocatalysts for metal-free ATRP.26, 27 Because researchers in the field of polymerization catalysis are constantly developing new catalytic systems, the ability to compare catalyst performance across a number of metrics is vital. This ability to make comparisons relies heavily upon procedural consistency and clarity on the part of the researchers performing the experiments. As such, it is our goal that this video will be used to help precisely communicate the methods by which these polymers are synthesized and characterized.

<table border="0" cellpadding="0" cellspacing="0" width="572">
	<tbody>
		<tr height="21">
			<td height="21" style="height:21px;width:205px;">perylene, min 98.0%</td>
			<td style="width:92px;">TCI America</td>
			<td style="width:128px;">TCP0078-025G</td>
			<td style="width:147px;">purify by sublimation</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:205px;">N,N-dimethylformamide</td>
			<td style="width:92px;">VWR</td>
			<td style="width:128px;">EM-DX1726-1</td>
			<td style="width:147px;">Omnisolv</td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;width:205px;">methyl methacrylate, 99%</td>
			<td style="width:92px;">VWR</td>
			<td style="width:128px;">200000-678</td>
			<td style="width:147px;">distilled prior to use, stored in refrigerator</td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;">ethyl &#945;-bromophenyl acetate&#160;</td>
			<td style="width:92px;">Aldrich</td>
			<td style="width:128px;">554065</td>
			<td style="width:147px;">distilled prior to use stored in refrigerator</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;">butylated hydroxytoluene&#160;</td>
			<td style="width:92px;">Aldrich</td>
			<td style="width:128px;">W218405</td>
			<td style="width:147px;"></td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;">Chloroform-D</td>
			<td style="width:92px;">Cambridge Isotope Labs</td>
			<td style="width:128px;">DLM-7-100</td>
			<td style="width:147px;"></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:205px;">tetrahydrofuran</td>
			<td style="width:92px;">VWR</td>
			<td style="width:128px;">EM-TX0279-1</td>
			<td style="width:147px;">Omnisolv</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:205px;">methanol</td>
			<td style="width:92px;">VWR</td>
			<td style="width:128px;">BDH1135</td>
			<td style="width:147px;"></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:205px;">dichloromethane</td>
			<td style="width:92px;">VWR</td>
			<td style="width:128px;">EM-DX0831-1</td>
			<td style="width:147px;">Omnisolv</td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;width:205px;">styrene, 99%</td>
			<td style="width:92px;">VWR</td>
			<td style="width:128px;">AAAA18481-0F</td>
			<td style="width:147px;">distilled prior to use, stored in refrigerator</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:205px;">glass scintillation vial, 20 mL</td>
			<td style="width:92px;">VWR</td>
			<td style="width:128px;">66022-065</td>
			<td style="width:147px;"></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:205px;">screw top vial, 2 mL</td>
			<td style="width:92px;">Agilent</td>
			<td style="width:128px;">5182-0715</td>
			<td style="width:147px;"></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:205px;">septum cap for screw top vial</td>
			<td style="width:92px;">Agilent</td>
			<td style="width:128px;">5182-0717</td>
			<td style="width:147px;"></td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;width:205px;">heavy wall pressure vessel, 100 mL</td>
			<td style="width:92px;">Synthware</td>
			<td style="width:128px;">P160005&#160;</td>
			<td style="width:147px;"></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:205px;">syringe, 1 mL norm-ject</td>
			<td style="width:92px;">VWR</td>
			<td style="width:128px;">89174-491</td>
			<td style="width:147px;"></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:205px;">NMR tube</td>
			<td style="width:92px;">New Era</td>
			<td style="width:128px;">NE-UL5-7&#39;</td>
			<td style="width:147px;"></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:205px;">nylon syringe filter, 0.45 um</td>
			<td style="width:92px;">VWR</td>
			<td style="width:128px;">28143-240</td>
			<td style="width:147px;"></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:205px;">glovebox</td>
			<td style="width:92px;">Mbraun</td>
			<td style="width:128px;">LABstar</td>
			<td style="width:147px;"></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:205px;">solvent purification system</td>
			<td style="width:92px;">Mbraun</td>
			<td style="width:128px;">MB-SPS-800</td>
			<td style="width:147px;"></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:205px;">stirplate</td>
			<td style="width:92px;">IKA</td>
			<td style="width:128px;">3582401</td>
			<td style="width:147px;"></td>
		</tr>
		<tr height="84">
			<td height="84" style="height:84px;width:205px;">light-emitting diodes</td>
			<td style="width:92px;">Creative Lighting Solutions</td>
			<td style="width:128px;">CL-FRS1210-5M-12V-WH</td>
			<td style="width:147px;">2x 12-inch strips of 5500 K white LEDs were used for illumination</td>
		</tr>
		<tr height="63">
			<td height="63" style="height:63px;width:205px;">12V DC power supply for LEDs</td>
			<td style="width:92px;">Creative Lighting Solutions</td>
			<td style="width:128px;">CL-PS16001-40W</td>
			<td style="width:147px;"></td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;width:205px;">high performance liquid chromatograph&#160;</td>
			<td style="width:92px;">Agilent</td>
			<td style="width:128px;">G1310B, G1322A, G1329B, G1316A</td>
			<td style="width:147px;"></td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;width:205px;">gel permeation size-exclusion columns</td>
			<td style="width:92px;">Agilent</td>
			<td style="width:128px;">PL1110-6500</td>
			<td style="width:147px;"></td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;width:205px;">multi-angle light scattering detector</td>
			<td style="width:92px;">Wyatt</td>
			<td style="width:128px;">WTREOS</td>
			<td style="width:147px;"></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:205px;">differential refractometer</td>
			<td style="width:92px;">Wyatt</td>
			<td style="width:128px;">WTREX</td>
			<td style="width:147px;"></td>
		</tr>
	</tbody>
</table>

atom transfer radical polymerization of functionalized vinyl monomers using perylene as a visible light photocatalyst

A standardized technique for atom transfer radical polymerization of vinyl monomers using perylene as a visible-light photocatalyst is presented. The procedure is performed under an inert atmosphere using air- and water-exclusion techniques. The outcome of the polymerization is affected by the ratios of monomer, initiator, and catalyst used as well as the reaction concentration, solvent, and nature of the light source. Temporal control over the polymerization can be exercised by turning the visible light source off and on. Low dispersities of the resultant polymers as well as the ability to chain-extend to form block copolymers suggest control over the polymerization, while chain end-group analysis provides evidence supporting an atom-transfer radical polymerization mechanism.

Tabla 1 muestra el rango de resultados de la polimerización alcanzables a través de este método. Estos datos muestran que perileno es capaz de servir como un fotocatalizador para la polimerización de un número de monómeros de vinilo funcionalizados. Para un monómero específico, el ajuste de cualquiera de un número de parámetros de reacción tales como disolvente, estequiometría, iniciador, y la fuente de luz conduce a polímeros con diferentes pesos moleculare...

Watch this Scientific Journal Video about Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst at JoVE.com

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Transferencia átomo de polimerización por radicales de monómeros funcionalizados vinilo Uso de perileno como fotocatalizador luz visible

A method for the atom transfer radical polymerization of functionalized vinyl monomers using perylene as a visible-light photocatalyst is described.

A standardized technique for atom transfer radical polymerization of vinyl monomers using perylene as a visible-light photocatalyst is presented. The ...

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Química

Synthesis and Characterization of Functionalized Metal-organic Frameworks

Marcos de síntesis y caracterización de funcionalizado metal-orgánico

Metal-organic frameworks have attracted extraordinary amounts of research attention, as they are attractive candidates for numerous industrial and ...

Real-time Monitoring of Reactions Performed Using Continuous-flow Processing: The Preparation of 3-Acetylcoumarin as an Example

Monitoreo en tiempo real de reacciones realizadas Utilizando Procesamiento de flujo continuo: La Preparación de 3-Acetylcoumarin como ejemplo

By using inline monitoring, it is possible to optimize reactions performed using continuous-flow processing in a simple and rapid way. It is also possible ...

Using Polystyrene-block-poly(acrylic acid)-coated Metal Nanoparticles as Monomers for Their Homo- and Co-polymerization

Using Polystyrene-block-polyacrylic acid-coated Metal Nanoparticles as Monomers for Their Homo- and Co-polymerization

El uso de poliestireno<em&gt; Bloque</em&gt; Poli (ácido acrílico) presenta el revestimiento de metal nanopartículas como monómeros para su homo- y co-polimerización

We present a template-free method for &#8220;polymerizing&#8221; nanoparticles into long chains without side branches. A variety of nanoparticles are ...

Ethylene Polymerizations Using Parallel Pressure Reactors and a Kinetic Analysis of Chain Transfer Polymerization

Las polimerizaciones de etileno utilizando reactores de presión paralelas y un análisis cinético de la cadena de transferencia de polimerización

We demonstrate a method for high-throughput catalyst screening using a parallel pressure reactor starting from the initial synthesis of a nickel ...

Development of a Backbone Cyclic Peptide Library as Potential Antiparasitic Therapeutics Using Microwave Irradiation

Desarrollo de un Backbone cíclica Péptido Biblioteca como Potencial Antiparasitarios Terapéutica Utilizando Microondas irradiación

Protein-protein interactions (PPIs) are intimately involved in almost all biological processes and are linked to many human diseases. Therefore, there is ...

Facile Synthesis of Worm-like Micelles by Visible Light Mediated Dispersion Polymerization Using Photoredox Catalyst

Síntesis Facile de micelas similares a gusanos de luz visible mediada por dispersión Polimerización con catalizador Photoredox

Presented herein is a protocol for the facile synthesis of worm-like micelles by visible light mediated dispersion polymerization. This approach begins ...

A Simple and Efficient Protocol for the Catalytic Insertion Polymerization of Functional Norbornenes

Un protocolo simple y eficaz para la inserción catalítico de polimerización norbornenos funcionales

Norbornene can be polymerized by a variety of mechanisms, including insertion polymerization whereby the double bond is polymerized and the bicyclic ...

Preparation of Hollow Polystyrene Particles and Microcapsules by Radical Polymerization of Janus Droplets Consisting of Hydrocarbon and Fluorocarbon Oils

Preparación de partículas de poliestireno hueco y microcápsulas por polimerización Radical de Janus gotas de hidrocarburos y aceites de fluorocarbono

In this article, we have demonstrated a method for producing hollow particles and microcapsules using oil droplets consisting of hydrocarbon oil (styrene) ...

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Construcción de Thioether/sulfuro de vinilo-atado Hydrothiolation de péptidos helicoidales mediante foto-inducida tiol-eno/Ino

Here, we describe a detailed protocol for the preparation of thioether-tethered peptides using on-resin intramolecular/intermolecular thiol-ene ...