Acid‐Induced Shift of Intramolecular Hydrogen Bonding Responsible for Excited‐State Intramolecular Proton Transfer

Wang Qin; Niu Yahui; Wang Rong; Wu Haoran; Zhang Yanrong

摘要

Abstract >The significant progress recently achieved in designing smart acid‐responsive materials based on intramolecular charge transfer inspired us to utilize excited‐state intramolecular proton transfer (ESIPT) for developing a turn‐on acid‐responsive fluorescent system with an exceedingly large Stokes shift. Two ESIPT‐active fluorophores, 2‐(2‐hydroxyphenyl)pyridine (HPP) and 2‐(2‐hydroxyphenyl)benzothiazole (HBT), were fused into a novel dye (HBT‐HPP) fluorescent only in the protonated state. Moreover, we also synthesized three structurally relevant control compounds to compare their steady‐state fluorescence spectra and optimized geometric structures in neutral and acidic media. The results suggest that the fluorescence turn‐on was caused by the acid‐induced shift of the ESIPT‐responsible intramolecular hydrogen bond from the HPP to HBT moiety. This work presents a systematic comparison of the emission efficiencies and basicity of HBT and HPP for the first time, thereby utilizing their differences to construct an acid‐responsive smart organic fluorescent material. As a practical application, red fluorescent letters can be written using the acid as an ink on polymer film. </abstract> </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”xml：lang =“en”> <标题类型=“main”>抽象</ title> >最近在基于分子内电荷转移设计智能酸性响应材料时实现的显着进展激发了我们利用兴奋状态分子内质子转移（ESIPT），用于开发带有非常大的斯托克斯换档的开启酸性响应荧光系统。两个eSipti活性荧光团，2-（2-羟基苯基）吡啶（HPP）和2-（2-羟基苯基）苯并噻唑（HBT）仅在质子化状态下融合成新型染料（HBT-HPP）荧光。此外，我们还合成了三种结构相关的对照化合物，以比较它们的稳态荧光光谱和中性和酸性介质的优化几何结构。结果表明，荧光开启是由来自HPP到HBT部分的依es敏感性分子内氢键的酸诱导的差移引起的。这项工作首次提出了对HBT和HPP的排放效率和碱度的系统性比较，从而利用它们的差异来构建酸响应性智能有机荧光材料。作为实际应用，可以使用酸作为聚合物膜上的墨水写入红色荧光字母。</ p> </摘要> </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-16161/'>《Chemistry, an Asian journal》</a> <b style="margin: 0 2px;">|</b><span>2018年第13期</span><b style="margin: 0 2px;">|</b><span>共9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=Wang Qin&option=202" target="_blank" rel="nofollow">Wang Qin;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Niu Yahui&option=202" target="_blank" rel="nofollow">Niu Yahui;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Wang Rong&option=202" target="_blank" rel="nofollow">Wang Rong;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Wu Haoran&option=202" target="_blank" rel="nofollow">Wu Haoran;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhang Yanrong&option=202" target="_blank" rel="nofollow">Zhang Yanrong;</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>College of Chemistry &</p> <p>PharmacyNorthwest A&</p> <p>F UniversityYangling Shaanxi 712100 P. R. China;</p> <p>College of Chemistry &</p> <p>PharmacyNorthwest A&</p> <p>F UniversityYangling Shaanxi 712100 P. R. China;</p> <p>College of Chemistry &</p> <p>PharmacyNorthwest A&</p> <p>F UniversityYangling Shaanxi 712100 P. R. China;</p> <p>Innovation Experimental CollegeNorthwest A&</p> <p>F UniversityYangling Shaanxi 712100 P. R. China;</p> <p>College of Chemistry &</p> <p>PharmacyNorthwest A&</p> <p>F UniversityYangling Shaanxi 712100 P. R. China;</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/159.html" title="化学">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=density functional calculations&option=203" rel="nofollow">density functional calculations;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=fluorescence&option=203" rel="nofollow">fluorescence;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=hydrogen bonds&option=203" rel="nofollow">hydrogen bonds;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=protonation&option=203" rel="nofollow">protonation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=theoretical calculations&option=203" rel="nofollow">theoretical calculations;</a> </p> <div class="translation"> 机译：密度函数计算;荧光;氢键;质子化;理论计算; </div> </li> </ul> </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/0704022087268.html">Acid‐Induced Shift of Intramolecular Hydrogen Bonding Responsible for Excited‐State Intramolecular Proton 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</span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-29680_thesis/020222245372.html">基于激发态分子间质子转移响应机理的阴离子荧光传感</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=郭琳&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 郭琳</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=张晗&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,张晗</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=张煊&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,张煊</a> <span> <a href="/conference-cn-29680/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 第八届中国化学会分析化学年会暨第八届全国原子光谱学术会议 </a> <span> <span> . 2003</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020315863864.html">激发态分子内和分子间多质子转移机理与调控</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=赵金峰&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 赵金峰</a> <span> . 2020</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120109821417.html">一种基于聚集诱导发光和激发态分子内质子转移化合物及其制备方法和应用</a> <b>[P]</b> . <span> 中国专利： CN107311957A </span> <span> . 2017-11-03</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/061201377475.html">利用激发态分子内质子转移特性的白色发光单分子化合物、及包含该化合物的有机电致发光元件及激光元件</a> <b>[P]</b> . <span> 中国专利： CN102395647B </span> <span> . 2014.05.14</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130403980686.html">INITIATORS OF RADICAL POLYMERIZATION BY FLUORESCENT ATTRAN TRANSFER VIA THE INTRAMOLECULAR PROTONIC TRANSFER IN THE EXCITED STATE (ESIPT) AND FLUORESCENT POLYMERS OBTAINED BY THIS METHOD</a> <b>[P]</b> . <span> 外国专利：  BR102017026077A2 </span> <span> . 2019-06-25</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：通过激发态的分子内质子转移（ESIPT）和通过这种方法获得的含氟聚合物，通过荧光原子转移进行自由基聚合的引发剂 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130501402214.html">COMPOUNDS HAVING EXCITED STATE INTRAMOLECULAR PROTON TRANSFER (ESIPT) CHARACTER FOR USE IN TREATING AND/OR PREVENTING SUNBURN AND/OR PREVENTING U.V. 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