A new design of cleavable acetal‐containing amphiphilic block copolymers triggered by light

Huang Yu; Thanneeru Srinivas; Zhang Qian; He Jie

摘要

ABSTRACT > We report a new design of photolabile acetal‐containing amphiphilic block copolymers. Acetals as protecting groups for carbonyls or diols can be hydrolyzed under acidic condition but very stable with respect to hydrolysis at pH??7. When combining light‐capturing chromophores with acetals, the hydrolysis of acetals can be activated by light to design dual responsive acetal‐containing polymers. Using acetalization reaction of 2,3‐dihydroxypropyl methacrylate with benzaldehyde derivatives, two new acetal‐containing photolyzable monomers have been designed. Comparable to commonly used photolabile monomers containing nitrobenzyl esters, the two acetal‐containing monomers are easy to polymerize using atom transfer radical polymerization with excellent molecular weight and dispersity control. We studied the cleavage kinetics and mechanism of acetal groups in both monomers and polyethylene oxide (PEO)‐containing amphiphilic block copolymers using 1 H NMR and UV–vis spectroscopy. o ‐Nitrobenzaldehyde acetal showed a Norrish Type II rearrangement to form benzoic ester; while, 2,5‐dimethoxy benzaldehyde acetal was photolabile to completely release 2,3‐dihydroxypropyl methacrylate. The photocleavage of acetals is a zero‐order reaction in regardless of molecular states of acetals; while, the acid‐cleavage of acetals proves to be a first‐order kinetics and the cleavage becomes much slower for polymers. The self‐assembly of acetal‐containing amphiphilic block copolymers and the acid‐/light‐controlled dissociation of their vesicles have been investigated. We demonstrate that those acetal‐containing polymers are potentially useful as smart drug delivery systems where the release kinetics of payloads is tunable using light and pH as triggers. ? 2018 Wiley Periodicals, Inc. J. Po </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> <div class="translation abstracttxt"> <span class="zhankaihshouqi fivelineshidden" id="abstract"> <span>机译：</span><abstract xmlns =“http://www.wiley.com/namespaces/wiley”type =“main”> <title type =“main”>抽象</ title> >我们报告了一个新设计的光图缩醛 - 含有两亲嵌段共聚物。作为羰基或二醇的保护基团的缩醛可以在酸性条件下水解，但相对于pH值的水解非常稳定。β7。当用缩醛结合光捕获的发色团时，缩醛的水解可以通过光激活，以设计双响应缩醛的聚合物。使用与苯甲醛衍生物2,3-二羟基丙基甲基丙烯酸丙烯酸丙烯酸甲酯的缩醛反应，已经设计了两种新的含缩醛的可光脱离单体。可与含硝基苄基酯的常用光塑料单体相当，使用具有优异分子量和分散性控制的原子传递自由基聚合易于聚合两种含缩醛单体。我们研究了使用 1℃和uV-Vis光谱法在单体和聚环氧乙烷（PEO）中缩醛组和聚环氧乙烷（PEO）甲基嵌段共聚物中的缩醛基团的切割动力学和机制。 o </ i> - 硝基苯甲醛缩醛显示鼻子II型重排，形成苯甲酸苯甲酸苯甲酸酯;虽然，2,5-二甲氧基苯甲醛缩醛是光致的，以完全释放2,3-二羟基丙基甲基丙烯酸酯。无论缩醛的分子状态如何，缩醛的光荧光是零级反应;虽然，缩醛的酸性切割被证明是一阶动力学，并且聚合物的裂解变慢得多。已经研究了含缩醛的两亲嵌段共聚物的自组装和其囊泡的酸/光控制的离解。我们证明这些含缩醛的聚合物可能是可用作智能药物递送系统，其中有效载荷的释放动力学使用光和pH作为触发器可调。还是2018 Wiley期刊，Inc。J.Po </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> </div> <div class="record"> <h2 class="all_title" id="enpatent33" >著录项</h2> <ul> <li> <span class="lefttit">来源</span> <div style="width: 86%;vertical-align: text-top;display: inline-block;"> <a href='/journal-foreign-35621/'>《Journal of Polymer Science, Part A. Polymer Chemistry》</a> <b style="margin: 0 2px;">|</b><span>2018年第16期</span><b style="margin: 0 2px;">|</b><span>共11页</span> </div> </li> <li> <div class="author"> <span class="lefttit">作者</span> <p id="fAuthorthree" class="threelineshidden zhankaihshouqi"> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Huang Yu&option=202" target="_blank" rel="nofollow">Huang Yu;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Thanneeru Srinivas&option=202" target="_blank" rel="nofollow">Thanneeru Srinivas;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhang Qian&option=202" target="_blank" rel="nofollow">Zhang Qian;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=He Jie&option=202" target="_blank" rel="nofollow">He Jie;</a> </p> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zkzz" style="display: none;">展开▼</span> </div> </li> <li> <div style="display: flex;"> <span class="lefttit">作者单位</span> <div style="position: relative;margin-left: 3px;max-width: 639px;"> <div class="threelineshidden zhankaihshouqi" id="fOrgthree"> <p>Department of ChemistryUniversity of ConnecticutStorrs Connecticut 06269;</p> <p>Department of ChemistryUniversity of ConnecticutStorrs Connecticut 06269;</p> <p>Department of Applied Chemistry School of SciencesXi'an University of Technology 710048Xi'an Shaanxi People's Republic of China;</p> <p>Department of ChemistryUniversity of ConnecticutStorrs Connecticut 06269;</p> </div> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zhdw" style="display: none;">展开▼</span> </div> </div> </li> <li > <span class="lefttit">收录信息</span> <span style="width: 86%;vertical-align: text-top;display: inline-block;"></span> </li> <li> <span class="lefttit">原文格式</span> <span>PDF</span> </li> <li> <span class="lefttit">正文语种</span> <span>eng</span> </li> <li> <span class="lefttit">中图分类</span> <span><a href="https://www.zhangqiaokeyan.com/clc/1184.html" title="有机化学">有机化学;</a></span> </li> <li class="antistop"> <span class="lefttit">关键词</span> <p style="width: 86%;vertical-align: text-top;"> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=acetal&option=203" rel="nofollow">acetal;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=nitrobenzyl esters&option=203" rel="nofollow">nitrobenzyl esters;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=photolysis&option=203" rel="nofollow">photolysis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=photoresponsive polymers&option=203" rel="nofollow">photoresponsive polymers;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=responsive micelles&option=203" rel="nofollow">responsive micelles;</a> </p> <div class="translation"> 机译：缩醛;硝基苄基酯;光解;光反应聚合物;响应胶束; </div> </li> </ul> </div> </div> <div class="literature cardcommon" id="literaturereference" style="display:none"> <div class="similarity "> <h3 class="all_title" id="enpatent111">引文网络</h3> <div class="referencetab clearfix"> <ul id="referencedaohang"> <li dataid="referenceul">参考文献</li> <li dataid="citationul">引证文献</li> <li dataid="commonreferenceul">共引文献</li> <li dataid="commoncitationul">同被引文献</li> <li dataid="tworeferenceul">二级参考文献</li> <li dataid="twocitationul">二级引证文献</li> </ul> </div> <div class="reference_details" id="referenceList"> <ul id="referenceul"></ul> <ul id="citationul"></ul> <ul id="commonreferenceul"></ul> <ul id="commoncitationul"></ul> <ul id="tworeferenceul"></ul> <ul id="twocitationul"></ul> </div> </div> </div> <div class="literature cardcommon"> <div class="similarity "> <h3 class="all_title" id="enpatent66">相似文献</h3> <div class="similaritytab clearfix"> <ul> <li class="active" >外文文献</li> <li >中文文献</li> <li >专利</li> </ul> </div> <div class="similarity_details"> <ul > <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/0704020725937.html">A new design of cleavable acetal‐containing amphiphilic block copolymers triggered by light</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Huang Yu&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Huang Yu,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Thanneeru Srinivas&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Thanneeru Srinivas,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhang Qian&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Zhang Qian,</a> <a href="/journal-foreign-35621/" target="_blank" rel="nofollow" class="tuijian_authcolor">Journal of Polymer Science, Part A. 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