Name: facile synthesis of worm-like micelles by visible light mediated dispersion polymerization using photoredox catalyst
Uploaded: 2016-06-08T15:00:00
Description: Watch this Scientific Journal Video about Facile Synthesis of Worm-like Micelles by Visible Light Mediated Dispersion Polymerization Using Photoredox Catalyst at JoVE.com

CB is thankful for his Future Fellowship from Australian Research Council (ARC-FT12010096) and UNSW Australia.

1. 합성 및 POEGMA의 특성 매크로 CTA <ol><li> 올리고 (에틸렌 글리콜) 메틸 에테르 메타 크릴 레이트 (OEGMA) (12g, 4 × 10-2 몰), 4- 시아 노 -4- (phenylcarbonothioylthio) 펜 탄산 (CPADB) (0.224 g, 8 × 10-4 몰)을 추가 2,2&#39;- 아조 비스 (2- 메틸 프로 피오 니트릴) (AIBN)을 100 ㎖ 둥근 바닥 플라스크 (16.4 ㎎, 0.1 mmol) 및 50 mL의 아세토 니트릴 (MeCN 중). </li><li> 적절한 크기의 고무 격막 및 강선 플라스크를 밀?...

<ol>
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Soc. 135 (36), 13574-13581 (2013).</li><li>Sugihara, S., Blanazs, A., Armes, S. P., Ryan, A. J., Lewis, A. L. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Aqueous+Dispersion+Polymerization:+A+New+Paradigm+for+in+Situ+Block+Copolymer+Self-Assembly+in+Concentrated+Solution.">Aqueous Dispersion Polymerization: A New Paradigm for in Situ Block Copolymer Self-Assembly in Concentrated Solution.</a> J. Am. Chem. Soc. 133 (39), 15707-15713 (2011).</li><li>Wan, W. M., Hong, C. Y., Pan, C. Y. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=One-pot+synthesis+of+nanomaterials+via+RAFT+polymerization+induced+self-assembly+and+morphology+transition.">One-pot synthesis of nanomaterials via RAFT polymerization induced self-assembly and morphology transition.</a> Chem. Comm. (39), 5883-5885 (2009).</li><li>Semsarilar, M., Jones, E. R., Blanazs, A., Armes, S. P. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Efficient+Synthesis+of+Sterically-Stabilized+Nano-Objects+via+RAFT+Dispersion+Polymerization+of+Benzyl+Methacrylate+in+Alcoholic+Media.">Efficient Synthesis of Sterically-Stabilized Nano-Objects via RAFT Dispersion Polymerization of Benzyl Methacrylate in Alcoholic Media.</a> Adv. Mater. 24 (25), 3378-3382 (2012).</li><li>Karagoz, B., 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=Polymerization-Induced+Self-Assembly+(PISA)+-+control+over+the+morphology+of+nanoparticles+for+drug+delivery+applications.">Polymerization-Induced Self-Assembly (PISA) - control over the morphology of nanoparticles for drug delivery applications.</a> Polym. Chem. 5 (2), 350-355 (2014).</li><li>Geng, Y., 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=Shape+effects+of+filaments+versus+spherical+particles+in+flow+and+drug+delivery.">Shape effects of filaments versus spherical particles in flow and drug delivery.</a> Nat Nano. 2 (4), 249-255 (2007).</li><li>Blanazs, 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=Sterilizable+gels+from+thermoresponsive+block+copolymer+worms.">Sterilizable gels from thermoresponsive block copolymer worms.</a> J. Am. Chem. Soc. 134 (23), 9741-9748 (2012).</li><li>Pei, Y., Thurairajah, L., Sugita, O. R., Lowe, A. B. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=RAFT+Dispersion+Polymerization+in+Nonpolar+Media:+Polymerization+of+3-Phenylpropyl+Methacrylate+in+n-Tetradecane+with+Poly(stearyl+methacrylate)+Homopolymers+as+Macro+Chain+Transfer+Agents.">RAFT Dispersion Polymerization in Nonpolar Media: Polymerization of 3-Phenylpropyl Methacrylate in n-Tetradecane with Poly(stearyl methacrylate) Homopolymers as Macro Chain Transfer Agents.</a> Macromolecules. 48 (1), 236-244 (2015).</li><li>Fielding, L. A., Lane, J. A., Derry, M. J., Mykhaylyk, O. O., Armes, S. P. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Thermo-responsive+Diblock+Copolymer+Worm+Gels+in+Non-polar+Solvents.">Thermo-responsive Diblock Copolymer Worm Gels in Non-polar Solvents.</a> J. Am. Chem. Soc. 136 (15), 5790-5798 (2014).</li><li>Yeow, J., Xu, J., Boyer, C. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Polymerization-Induced+Self-Assembly+Using+Visible+Light+Mediated+Photoinduced+Electron+Transfer-Reversible+Addition-Fragmentation+Chain+Transfer+Polymerization.">Polymerization-Induced Self-Assembly Using Visible Light Mediated Photoinduced Electron Transfer-Reversible Addition-Fragmentation Chain Transfer Polymerization.</a> ACS Macro Lett. 4 (9), 984-990 (2015).</li><li>Xu, J., Jung, K., Corrigan, N. A., Boyer, C. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Aqueous+photoinduced+living/controlled+polymerization:+tailoring+for+bioconjugation.">Aqueous photoinduced living/controlled polymerization: tailoring for bioconjugation.</a> Chem. Sci. 5 (9), 3568-3575 (2014).</li><li>Pei, Y., 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=RAFT+dispersion+polymerization+of+3-phenylpropyl+methacrylate+with+poly[2-(dimethylamino)ethyl+methacrylate]+macro-CTAs+in+ethanol+and+associated+thermoreversible+polymorphism.">RAFT dispersion polymerization of 3-phenylpropyl methacrylate with poly[2-(dimethylamino)ethyl methacrylate] macro-CTAs in ethanol and associated thermoreversible polymorphism.</a> Soft Matter. 10 (31), 5787-5796 (2014).</li></ol>

이 시각 프로토콜은 단순히 겔상 동작의 개시를 관찰함으로써 웜 같은 미셀의 형성을 모니터링하는 능력을 보여준다. 이 접근 방법의 유용성은 다른 방법에 비해 중합시 벌레의 형성을 모니터링 할 수있는 능력에있다. 이 과정은 자기 조립 POEGMA- ㄴ -PBzMA 양친 성 블록 공중 합체를 수득 개의 시판 단량체 (OEGMA 및 BZMA)의 2 단계 중합을 사용하여 수행 될 수있다. 도...

비구면 (및 기타) 나노 입자 모폴로지의 합성은 전통적으로 잘 정의 된 양친 성 이중 블록 (또는 다중 블록) 공중 합체의 합성과 정제로 시작하는 다단계 자기 조립 과정을 사용하여 달성되었다. 일반적인 자기 조립 기술 중 하나는 1990 년 아이젠 대중화와 블록 1-3 중 하나의 용제 선택의 느린 첨가하여 두 중합체 블록에 대한 공통 용매에 양친 성 블록 공중 합체의 용해를 포함시켰다 . 선택적 용매 (전형적으로 물)를 첨가함에 따라, 상기 블록 공중 합체는 중합체 나노 입자를 형성하기 위해 자기 조립을 겪는다. 최종 형태 (또는 모폴로지의 혼합물) 나노 입자는 예컨대, 각 중합체 블록의 물 첨가 속도와 공통 용매의 성질의 상대 길이로 많은 요소에 의해 결정된다. 그러나이 방법은 일반적으로 단지 nanopar의 생산을 허용상대적으로 낮은 고체 함량 (이하 1 중량 %)에 ticles 등의 실제적인 확장 성 (4)를 제한한다. 또, 웜 형상 미셀 같은 &quot;중간&quot;단계의 재현 형성이 비구면 형태 (5)을 안정화하기 위해 필요한 파라미터의 좁은 범위로 인해 어려울 수있다. 중합 유도 자기 조립 (PISA) 방식은 부분적으로 나노 입자의 합성을 가능 시츄 자기 조립체를 구동하기 위해 중합 공정을 훨씬 높은 고형분 자체를 이용하여 아이젠 방법의 단점을 해결 (전형적으로 10 내지 30 중량 %) 6 -8. 전형적인 PISA 접근법에서, 리빙 중합 방법은 반응 매질에서 가용성이지만 초기에 불용성 중합체를 형성하는 단량체와 용매 가용성 매크로 개시제 (또는 매크로 CTA)을 쇄 연장 사용된다. 피사 방식 체계적 예들을 테스트하여 웜 같은 미셀을 합성하는데 사용 된<html> perimental 매개 변수와 합성 &quot;로드맵&quot;5,9 등 자세한 위상 다이어그램을 사용하여. 그들의 도전 합성에도 불구하고, 그들의 구면 대응에 대해 자신의 흥미로운 속성에 벌레 모양의 나노 입자에 큰 관심이있다. 예를 들어, 우리는 PISA 접근법을 사용하여 합성 약물로드 짧고 긴 웜 같은 미셀이 구형 또는 미셀에 비해 소포 10 시험 관내 세포 독성에 상당히 높은 있다고 설명했다. 기타 생체 내 모델 (11)에 나노 입자의 종횡비 및 혈액 순환 시간 사이의 상관 관계를 보여 주었다. 기타 적절한 PISA 방법론을 이용하여 웜과 같은 나노 입자의 합성에 의한 나노 섬유의 얽힘에 나노 거시적 겔을 얻을 수 있음을 보여 주었다. 이 젤은 열 가역 졸 - 겔 (sol-gel) 동작 (12)에 의해 살균 젤 잠재적 증명하고있다. &quot;ontent&gt;이 프로토콜은 단순히 중합시 용액 점도를 관찰함으로써 웜 같은 미셀의 형성 시츄 모니터링을 허용하는 방법을 설명한다. 유사한 웜 형상 미셀 겔의 이전 연구는 임계 온도 이상으로, 이들을 증명 나노 입자는 가역적 웜 구 천이를 겪게 때문에 고온에서 자유 유동 분산액을 형성한다. 현재까지 이러한 시스템이 겔화 용이 이러한 시스템에서 관찰되지 않을 수있다 (13, 14) 등 제어 중합 개시 감열 아조 화합물을 이용했다 열 중합.이 연구 동안, 낮은 온도에서 PISA 유도 된 나노 입자를 합성하는 반응계이 겔화 거동의 관찰을 허용 할 수 있다고 가정 하였다. 최근 우리의 나노 입자를 수득 할 PISA 과정을 중재하는 손쉬운 실온 광중합 기술의 사용을보고다른 형태학 15. 여기서, 시각 프로토콜은 중합시 용액 점도 거동을 관찰함으로써 웜 같은 미셀의 재현성이 합성되게된다. 분산 중합으로 진행 용이하게 시판되는 발광 다이오드 (LED)를 사용하여 (λ = 460 nm의, 0.7 mW의 / cm 2).

<table border="1" fo:keep-together.within-page="1" fo:keep-with-next.within-page="always">
	<tbody>
		<tr>
			<td>4-Cyano-4-(phenylcarbonothioylthio)pentanoic acid (CPADB)</td>
			<td>Sigma-Aldrich</td>
			<td>722995-5G</td>
			<td></td>
		</tr>
		<tr>
			<td>Oligo(ethylene glycol) methyl ether methacrylate (OEGMA)</td>
			<td>Sigma-Aldrich</td>
			<td>447935-500ML</td>
			<td>Average Mn 300, contains 100&#160;ppm MEHQ as inhibitor, 300&#160;ppm BHT as inhibitor</td>
		</tr>
		<tr>
			<td>2,2&#8242;-Azobis(2-methylpropionitrile) (AIBN)</td>
			<td>Sigma-Aldrich</td>
			<td></td>
			<td></td>
		</tr>
		<tr>
			<td>Ru(bpy)3Cl2.6H2O</td>
			<td>Sigma-Aldrich</td>
			<td>544981-1G</td>
			<td></td>
		</tr>
		<tr>
			<td>Benzyl methacrylate (BzMA)</td>
			<td>Sigma-Aldrich</td>
			<td>409448-1L</td>
			<td>Contains monomethyl ether hydroquinone as inhibitor</td>
		</tr>
		<tr>
			<td>Aluminium oxide (basic)</td>
			<td>Chem-Supply Pty Ltd Australia</td>
			<td>AL08371000</td>
			<td></td>
		</tr>
		<tr>
			<td>95% Ethanol (EtOH)</td>
			<td>Sucrogen Bio Ethanol</td>
			<td>80889</td>
			<td></td>
		</tr>
		<tr>
			<td>Acetonitrile (MeCN)</td>
			<td>Chem-Supply Pty Ltd Australia</td>
			<td>RP1005-G2.5L</td>
			<td></td>
		</tr>
		<tr>
			<td>Tetrahydrofuran (THF)</td>
			<td>Chem-Supply Pty Ltd Australia</td>
			<td>TA011-2.5L</td>
			<td></td>
		</tr>
		<tr>
			<td>Petroleum Spirits (40-60oC)</td>
			<td>Chem-Supply Pty Ltd Australia</td>
			<td>PA044-2.5L</td>
			<td></td>
		</tr>
		<tr>
			<td>Diethyl Ether</td>
			<td>Chem-Supply Pty Ltd Australia</td>
			<td>EA0362.5L</td>
			<td></td>
		</tr>
		<tr>
			<td>Dimethylacetamide (DMAc)</td>
			<td>VWR International Australia</td>
			<td>ALFA22916.M1</td>
			<td>For GPC analysis</td>
		</tr>
		<tr>
			<td>Pasteur pipettes (230 mm)</td>
			<td>Labtek</td>
			<td>355.050.503</td>
			<td></td>
		</tr>
		<tr>
			<td>Glass beakers</td>
			<td>Labtek</td>
			<td>025.01.902 (2L)/ 2110654 (1L)</td>
			<td>2L beaker is for attaching LED strips to form the circular reactor</td>
		</tr>
		<tr>
			<td>Commercial LED strip</td>
			<td>EcoLab</td>
			<td>n/a</td>
			<td>&#955; = 460 nm, 4.8 W/m</td>
		</tr>
		<tr>
			<td>4 mL Glass Vials</td>
			<td>Labtek</td>
			<td>APC502214B</td>
			<td></td>
		</tr>
		<tr>
			<td>0.9 mL Quartz Cuvette</td>
			<td>Starna Scientific Ltd</td>
			<td>21/Q/2</td>
			<td></td>
		</tr>
		<tr>
			<td>Needle (0.8 mm x 38 mm)</td>
			<td>Beckton Dickson</td>
			<td>302017</td>
			<td>For deoxygenating reactions</td>
		</tr>
		<tr>
			<td>Needle (0.8 mm x 120 mm)</td>
			<td>B Braun Australia</td>
			<td>4665643</td>
			<td>For deoxygenating reactions</td>
		</tr>
		<tr>
			<td>Sleeve stopper septa (rubber septum)</td>
			<td>Sigma-Aldrich</td>
			<td>z564680/z564702</td>
			<td></td>
		</tr>
		<tr>
			<td>Stirring hotplates</td>
			<td>VWR International Australia/In Vitro Technologies</td>
			<td>97018-488/RADRR91200</td>
			<td></td>
		</tr>
		<tr>
			<td>Vortex mixer</td>
			<td>VWR International Australia</td>
			<td>412-0098</td>
			<td></td>
		</tr>
		<tr>
			<td>Vacuum oven</td>
			<td>In Vitro Technologies</td>
			<td>MEMVO200</td>
			<td></td>
		</tr>
	</tbody>
</table>

facile synthesis of worm-like micelles by visible light mediated dispersion polymerization using photoredox catalyst

Presented herein is a protocol for the facile synthesis of worm-like micelles by visible light mediated dispersion polymerization. This approach begins with the synthesis of a hydrophilic poly(oligo(ethylene glycol) methyl ether methacrylate) (POEGMA) homopolymer using reversible addition-fragmentation chain-transfer (RAFT) polymerization. Under mild visible light irradiation (&#955; = 460 nm, 0.7 mW/cm2), this macro-chain transfer agent (macro-CTA) in the presence of a ruthenium based photoredox catalyst, Ru(bpy)3Cl2 can be chain extended with a second monomer to form a well-defined block copolymer in a process known as Photoinduced Electron Transfer RAFT (PET-RAFT). When PET-RAFT is used to chain extend POEGMA with benzyl methacrylate (BzMA) in ethanol (EtOH), polymeric nanoparticles with different morphologies are formed in situ according to a polymerization-induced self-assembly (PISA) mechanism. Self-assembly into nanoparticles presenting POEGMA chains at the corona and poly(benzyl methacrylate) (PBzMA) chains in the core occurs in situ due to the growing insolubility of the PBzMA block in ethanol. Interestingly, the formation of highly pure worm-like micelles can be readily monitored by observing the onset of a highly viscous gel in situ due to nanoparticle entanglements occurring during the polymerization. This process thereby allows for a more reproducible synthesis of worm-like micelles simply by monitoring the solution viscosity during the course of the polymerization. In addition, the light stimulus can be intermittently applied in an ON/OFF manner demonstrating temporal control over the nanoparticle morphology.

본 연구에서는, 두 단계의 중합 프로토콜은 PISA 방법 (도 1)를 이용하여 웜 같은 미셀의 합성에 사용된다. 첫 번째 단계에서, OEGMA의 중합 후의 중합 공정에서 안정제로서 사용될 수 POEGMA 매크로 CTA를 산출을 행한다. 궁극적으로 나노 입자의 형성을 유도 PBzMA 에탄올 중 불용성으로 인해 분산 된 상태에서 PET-RAFT 중합을 진행한다. 중합 동안, 초기에 투명한 반응 ?...

Watch this Scientific Journal Video about Facile Synthesis of Worm-like Micelles by Visible Light Mediated Dispersion Polymerization Using Photoredox Catalyst at JoVE.com

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

This article describes a process for producing polymeric self-assembled nanoparticles using visible light mediated dispersion polymerization. Using low energy visible light to control the polymerization allows for the reproducible formation of self-assembled worm-like micelles at high solids content.

Photoredox 촉매를 사용하여 가시 광선 중재 분산 중합에 의해 웜 형상 미셀 손쉬운 합성

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

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JoVE Journal

Chemistry

Facile and Efficient Preparation of Tri-component Fluorescent Glycopolymers via RAFT-controlled Polymerization

RAFT 중합 제어를 통해 트라이 구성 요소 형광 Glycopolymers의 손쉬운 및 효율적인 준비

Synthetic glycopolymers are instrumental and versatile tools used in various biochemical and biomedical research fields. An example of a facile and ...

연구

화학

Facile Preparation of Internally Self-assembled Lipid Particles Stabilized by Carbon Nanotubes

탄소 나노 튜브에 의해 안정화 내부 자기 조립 된 지질 입자의 용이 한 제조

We present a facile method to prepare nanostructured lipid particles stabilized by carbon nanotubes (CNTs). Single-walled (pristine) and multi-walled ...

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

가시광 광촉매 페 릴렌 사용 관능 비닐 모노머의 원자 이동 라디칼 중합

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

Facile Preparation of 4-Substituted Quinazoline Derivatives

4 치환 된 퀴나 졸린 파생 상품의 손쉬운 준비

Reported in this paper is a very simple method for direct preparation of 4-substituted quinazoline derivatives from a reaction between substituted ...

HKUST-1 as a Heterogeneous Catalyst for the Synthesis of Vanillin

HKUST 바닐린-1의 합성에 대해 불균일 촉매로서

Vanillin (4-hydoxy-3-methoxybenzaldehyde) is the main component of the extract of vanilla bean. The natural vanilla scent is a mixture of approximately ...

Anionic Polymerization of an Amphiphilic Copolymer for Preparation of Block Copolymer Micelles Stabilized by &#960;-&#960; Stacking Interactions

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π-π 스태킹 상호 작용에 의해 안정화 된 블록 공중 합체 미셀 준비하는 양친 매성 공중 합체의 음이온 중합

In this study, an amphiphilic copolymer that includes a core-forming block with phenyl groups was synthesized by living anionic polymerization of phenyl ...

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

손쉬운 준비 (2<em&gt; Z</em&gt;, 4<em&gt; E</em&gt;) - 알렌 아세테이트를 이용한 전자 불충분 알켄의 합성에 의한 디에나 미이드

Direct cross-coupling between two alkenes via vinylic C-H bond activation represents an efficient strategy for the synthesis of butadienes with high ...

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

O-Carboxyanhydrides Ni/Zn 단지 중재의 Photoredox 반지 개통 중 합 제어

Here, we describe an effective protocol that combines photoredox Ni/Ir catalysis with the use of a Zn-alkoxide for efficient ring-opening polymerization, ...

Synthesis and Performance Characterizations of Transition Metal Single Atom Catalyst for Electrochemical CO2 Reduction

Synthesis and Performance Characterizations of Transition Metal Single Atom Catalyst for Electrochemical CO2 Reduction

합성 및 전기 화학적 CO2 감소를 위한 전이 금속 단일 원자 촉매의 성능 Characterizations

This protocol presents both the synthesis method of the Ni single atom catalyst, and the electrochemical testing of its catalytic activity and selectivity ...

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

반도체 Gyroidal 금속-황 프레임 워크의 결정 화에 대 한 Thiol 빌딩 블록의 합성

We present a method for preparing thioester molecules as the masked form of the thiol linkers and their utilization for accessing a semiconducting and ...