Name: controlled photoredox ring-opening polymerization of o-carboxyanhydrides mediated by ni/zn complexes
Uploaded: 2017-11-21T15:00:00
Description: Watch this Scientific Journal Video about Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes at JoVE.com

这项工作得到了弗吉尼亚理工学院和州立大学开办资金的支持。Q.F. 承认中国国家自然科学基金 (21504047)、江苏省自然科学基金 (BK20150834)、南京邮电大学科学基金 NUPTSF (NY214179) 的支持。

警告: 使用前请查阅所有相关材料安全数据表 (MSDS)。合成中使用的许多化学物质具有剧毒和致癌性。在执行反应时, 请使用所有适当的安全做法, 包括使用工程控制 (油烟罩和手套) 和个人防护用品 (安全眼镜、手套、实验室大衣、全长长裤、闭脚趾鞋、蓝光屏蔽安全护目镜)。以下程序涉及在手套箱中的标准无处理技术。所有的解决方案都是用吸管转移的。
1. 催化剂和引发剂的?...

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协议中的关键步骤是保持反应温度在-15 ±5° c。在聚合之前, 所有的催化剂溶液和亚奥基单体都必须在-35 ° c 的手套箱冷冻库中储存。在寒冷的陷阱中, 反应瓶必须预。在反应过程中, 由于 LED 灯散热, 必须每 15-20 分钟监测反应。一旦温度上升到-10 ° c, 液态氮应加入到杜瓦瓶冷却陷阱。低温的原因是室温下镍 (CO) 络合物的形成, 这对受控的 photoredox 聚合是不利的, 并影响到兆瓦和Đ。<sup class="xr...

聚 (α-羟基酸) (PAHA) 是一类重要的生物降解和生物相容性高分子材料, 其应用范围广泛, 从医用设备到包装原料。1,2虽然 PAHAs 可以通过α-羟基酸的缩聚直接制备, 但产生的 PAHAs 的分子量 (MWs) 普遍较低。3酯 (如丙交酯和乙) 的开环聚合 (ROP) 是一种替代合成方法, 可以更好地控制 MWs 和分子量分布 (Đ), 而不是缩聚。然而, PAHAs 和酯的侧链功能的缺乏限制了物理和化学性质及其应用的多样性。4,5自2006年以来, 13--1,3--24-diones, so-called O-carboxyanhydrides (oca), 可以用丰富多样的侧链功能编写,6,7,8,9,10,11,12,13已成为聚酯聚合中一种高活性单体的替代类。14,15
oca 的催化系统可分为有机、8、12、16、17有机金属催化剂12、18、19 ,20,21和催化剂。22一般情况下, 由有机促进的 oca 的 ROP 以或多或少不受控制的方式进行, 例如异构化 (即缺少 stereoregularity), 用于 oca 轴承电子提取组,8,17不可预知的 MWs, 或慢聚合动力学。13为了解决这些问题, 研制了一种活性锌-醇络合物, 用于 oca 的 ROP。12井控保护在低聚合 (DP) 的情况下, 没有异构化。然而, 这种锌-醇催化剂不能有效地产生高聚合度的聚合物 (DP ≥ 300)。13
我们最近报告了一种有希望的方法, 大大提高了 PAHA 合成的可和效率 (图 1)。13将 photoredox 镍/Ir 催化剂与锌醇脱, 以调节环开聚合 oca。低温 (-15 ° c) 和 photoredox 镍/Ir 催化的使用, 协同加速了脱链的传播, 同时避免了不受欢迎的副反应, 如镍羰基的形成。23,24在转移与 Ni 复合体的活性锌-醇位于链终点链传播。13
在本协议中, 我们添加新鲜准备 (bpy) Ni (COD) (bpy = 22 '-吡啶, COD = 15-1,5-), Zn (HMDS)2 (HMDS = 烷),25苄醇 (BnOH) 和 Ir [dF (CF3) 吡]2(dtbbpy) PF6 (Ir-1, dF (CF3) 吡 = 2-(24-氟)-5-三氟甲基吡啶, dtbbpy = 44 "-di-叔-butyl-2,2'-bipyridine) 到单体 l-1解决方案26在一个带有冷陷阱的手套箱中, 在一个蓝色 LED 灯 (400-500 nm) 和风扇以保持温度 (图 1)。在聚合过程中, 温度保持在-15 ° c ±5° c。采用傅里叶变换红外光谱法对亚奥氏转化率进行了监测。由此产生的聚合物 MWs 和Đs 的特点是凝胶渗透色谱 (GPC)。homodecoupling 的1H 核磁共振研究确定所得到的聚合物是否是规的。由于大多数化学品对湿气高度敏感, 详细的视频协议旨在帮助新的从业者避免与 oca photoredox ROP 相关的陷阱。

<table>
	<tbody>
		<tr>
			<td>Ni(COD)2</td>
			<td>Strem</td>
			<td>28-0010</td>
			<td>Stored in the glove box freezer.</td>
		</tr>
		<tr>
			<td>2,2&#8242;-bipyridine</td>
			<td>Strem</td>
			<td>07-0290</td>
			<td>Stored in the glove box freezer.</td>
		</tr>
		<tr>
			<td>Zn(HMDS)2</td>
			<td>N/A</td>
			<td>N/A</td>
			<td>Synthesized following reported procedures.25 Stored in the glove box freezer.</td>
		</tr>
		<tr>
			<td>Benzyl alcohol</td>
			<td>Sigma-Aldrich</td>
			<td>402834</td>
			<td>Stored with 4&#197; molecular sieve</td>
		</tr>
		<tr>
			<td>Ir[dF(CF3)ppy]2(dtbbpy)PF6</td>
			<td>Strem</td>
			<td>77-0425</td>
			<td>Stored in the glove box freezer.</td>
		</tr>
		<tr>
			<td>THF</td>
			<td>Sigma-Aldrich</td>
			<td>34865</td>
			<td>Dried by alumina columns and stored with 4&#197; molecular sieve in the dark bottle in the glove box.</td>
		</tr>
		<tr>
			<td>Ethanol</td>
			<td>Sigma-Aldrich</td>
			<td>793175</td>
			<td></td>
		</tr>
		<tr>
			<td>GPC with an isocratic pump</td>
			<td>Agilent</td>
			<td>Agilent 1260 series</td>
			<td></td>
		</tr>
		<tr>
			<td>Dawn Heleos II Light Scatterer</td>
			<td>Wyatt</td>
			<td></td>
			<td></td>
		</tr>
		<tr>
			<td>Optilab rEX differential refractive index detector</td>
			<td>Wyatt</td>
			<td></td>
			<td></td>
		</tr>
		<tr>
			<td>Size exclusion columns</td>
			<td>Phenomenex</td>
			<td></td>
			<td></td>
		</tr>
		<tr>
			<td>Glass Scintillation Vials - 7 ml</td>
			<td>VWR</td>
			<td></td>
			<td></td>
		</tr>
		<tr>
			<td>FTIR spectrometer</td>
			<td>Agilent</td>
			<td></td>
			<td></td>
		</tr>
		<tr>
			<td>Stir bars</td>
			<td>VWR</td>
			<td>58948-091</td>
			<td></td>
		</tr>
		<tr>
			<td>Balance</td>
			<td></td>
			<td></td>
			<td></td>
		</tr>
		<tr>
			<td>Glove box</td>
			<td>Mbraun</td>
			<td>Labstar Pro</td>
			<td></td>
		</tr>
	</tbody>
</table>

controlled photoredox ring-opening polymerization of o-carboxyanhydrides mediated by ni/zn complexes

在这里, 我们描述一个有效的协议, 结合 photoredox 镍/Ir 催化与使用锌醇的有效开环聚合, 允许合成的规聚 (α-羟基酸) 与预期的分子量 (> 140kDa) 和窄分子量分布 (Mw/mn < 1.1)。这种环开聚合由 Ni 和锌配合物在乙醇引发剂和 photoredox 红外催化剂的存在下进行介导, 由蓝色 LED (400-500 nm) 照射。在低温 (-15 ° c) 下进行聚合以避免不受欢迎的副反应。完整的单体消耗可以在 4-8 小时内完成, 为聚合物提供接近分子量的分子量分布。结果数字平均分子量显示一个线性相关与聚合程度1000。homodecoupling 的1H 核磁共振研究证实, 所获得的聚合物是规没有异构化。本文所报告的聚合提供了一种实现快速、受控的O-carboxyanhydrides 聚合的策略, 以制备 stereoregular 聚 (α-羟基酸) 及其承载各种功能侧链基团的共聚物。

通过傅里叶变换红外光谱对亚奥的转换进行监测, 如图 2所示。在 1805 cm-1的峰值被分配为在亚奥理事会中的酸酐粘结拉伸;峰值在 1760 cm-1对应于聚合物中酯键的形成。一旦单体的峰值在1805厘米-1完全消失, 聚合完成。
所产生的聚合物的兆瓦和Đ以凝胶渗透色谱为特征。<strong c...

Watch this Scientific Journal Video about Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes at JoVE.com

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

介绍了由 Ni/锌配合物介导的受控 photoredox 环开放聚合的O-carboxyanhydrides 的协议。

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

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抗癌金属配合物的合成与细胞毒性评价MTT法

Titanium (IV) and vanadium (V) complexes are highly potent anticancer agents. A challenge in their synthesis refers to their hydrolytic instability; ...

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

通过RAFT控制聚合轻便和高效制备三组分荧光Glycopolymers

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

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

乙烯聚合中使用并联电抗器的压力和链转移聚合的动力学分析

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

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

使用苝作为可见光光催化功能化的乙烯基单体原子转移自由基聚合

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

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

使用Photoredox催化剂蠕虫状胶束的简便合成可见光介导的分散聚合

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

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

Anionic Polymerization of an Amphiphilic Copolymer for Preparation of Block Copolymer Micelles Stabilized by ÃƒÆ’Ã‚ÂÃƒÂ¢Ã¢â‚¬Å¡Ã‚Â¬-ÃƒÆ’Ã‚ÂÃƒÂ¢Ã¢â‚¬Å¡Ã‚Â¬ Stacking Interactions

一个两亲性共聚物的阴离子聚合通过π-π堆积作用稳定嵌段共聚物胶束的制备

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

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

功能性降冰片烯的催化聚合插入一种简单高效的协议

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

Extraction of Ramie Fiber in Alkali Hydrogen Peroxide System Supported by Controlled-release Alkali Source

缓释碱源负载碱性过氧化氢体系中苎麻纤维的提取

This protocol demonstrates a method for ramie fiber extraction by scouring raw ramie in an alkali hydrogen peroxide system supported by a ...

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

由烃类和氟碳油组成的同液滴的自由基聚合制备空心聚苯乙烯颗粒和微胶囊

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