Synthesis of Fluoro and Cyanoaryl‐Containing Pyrene Derivatives and their Optical and Electrochemical Properties

Gong Xiaojie; Heeran Darren; Zhao Qiang; Zheng Chaoyue; Yufit Dmitry S.; Sandford Graham; Gao Deqing

摘要

Abstract >Mono‐ and 1,6‐disubstituted pyrene derivatives bearing perfluorotoluene or perfluorobenzonitrile moieties were synthesized by nucleophilic substitution processes. The compounds were characterized by NMR, UV‐vis, photoluminescence (PL), thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC), cyclic voltametry (CV) and density functional theory (DFT) calculations. It was found that derivatives substituted with perfluorobenzonitrile showed better thermal stability, stronger electron withdrawing ability and better fluorescence properties than the corresponding perfluorotoluyl‐pyrene systems </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 Type =“Main”XML：Lang =“en”> <标题类型=“main”>抽象</ title> 通过亲核取代方法合成携带全氟丙烯或全氟苄腈部分的单反二取代的芘衍生物。该化合物的特征在于NMR，UV-Vis，光致发光（PL），热重分析（TGA），差示扫描量热法（DSC），循环伏特法（CV）和密度泛函理论（DFT）计算。发现用全氟苄腈取代的衍生物显示出更好的热稳定性，较强的电子取出能力和比相应的全氟丙烯 - 芘系统更好的荧光性能</ 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-19765/'>《Asian Journal of Organic Chemistry》</a> <b style="margin: 0 2px;">|</b><span>2019年第5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=Gong Xiaojie&option=202" target="_blank" rel="nofollow">Gong Xiaojie;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Heeran Darren&option=202" target="_blank" rel="nofollow">Heeran Darren;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhao Qiang&option=202" target="_blank" rel="nofollow">Zhao Qiang;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zheng Chaoyue&option=202" target="_blank" rel="nofollow">Zheng Chaoyue;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yufit Dmitry S.&option=202" target="_blank" rel="nofollow">Yufit Dmitry S.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Sandford Graham&option=202" target="_blank" rel="nofollow">Sandford Graham;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Gao Deqing&option=202" target="_blank" rel="nofollow">Gao Deqing;</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>Key Laboratory of Flexible Electronics &</p> <p>Institute of Advanced Materials Jiangsu National synergistic Innovation Center for Advanced MaterialsNanjing Tech University NanjingJiangsu 211816 P.R. China;</p> <p>Department of ChemistryDurham UniversitySouth Road Durham DH1 3LE U.K;</p> <p>Key Laboratory of Flexible Electronics &</p> <p>Institute of Advanced Materials Jiangsu National synergistic Innovation Center for Advanced MaterialsNanjing Tech University NanjingJiangsu 211816 P.R. China;</p> <p>Key Laboratory of Flexible Electronics &</p> <p>Institute of Advanced Materials Jiangsu National synergistic Innovation Center for Advanced MaterialsNanjing Tech University NanjingJiangsu 211816 P.R. China;</p> <p>Department of ChemistryDurham UniversitySouth Road Durham DH1 3LE U.K;</p> <p>Department of ChemistryDurham UniversitySouth Road Durham DH1 3LE U.K;</p> <p>Key Laboratory of Flexible Electronics &</p> <p>Institute of Advanced Materials Jiangsu National synergistic Innovation Center for Advanced MaterialsNanjing Tech University NanjingJiangsu 211816 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/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=pyrene&option=203" rel="nofollow">pyrene;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=fluorine atom&option=203" rel="nofollow">fluorine atom;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Intramolecular charge transfer&option=203" rel="nofollow">Intramolecular charge transfer;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=n-type semiconductor&option=203" rel="nofollow">n-type semiconductor;</a> </p> <div class="translation"> 机译：芘;氟原子;分子内电荷转移;n型半导体; </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/0704022773794.html">Synthesis of Fluoro and Cyanoaryl‐Containing Pyrene Derivatives and their Optical and Electrochemical Properties</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Gong Xiaojie&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Gong Xiaojie,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Heeran Darren&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Heeran Darren,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhao Qiang&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Zhao Qiang,</a> <a href="/journal-foreign-19765/" target="_blank" rel="nofollow" class="tuijian_authcolor">Asian Journal of Organic Chemistry .</a> <span>2019</span><span>,第5期</span> </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：含氟和含氰芳基芘衍生物及其光学和电化学性能的合成</span> </p> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/0704013359278.html">Novel regular D-A-conjugated polymers based on 2,6-bis(6-fluoro-2-hexyl-2H-benzotriazol-4-yl)-4,4-bis(2-ethylhexyl)-4H-silolo[3,2-b:4,5-b']dithiophene derivatives: Synthesis, optoelectronic, and electrochemical properties</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Keshtov M. 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<span> <a href="/journal-cn-11569/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 合成化学 </a> </span> <span> . 2022</span><span>,第1期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-36144_thesis/020221425921.html">Ｎ－芳基－Ｎ′－（５－芳基－２－呋喃甲酰基）硫脲衍生物的合成及其生物活性的研究</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=陈继畴&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 陈继畴</a> <span> <a href="/conference-cn-36144/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 中国化工学会农药学会第六届年会 </a> <span> <span> . 1992</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020314314534.html">具有生物活性的含氮杂环化合物的合成(Ⅰ)：N-取代哌啶酮肟醚衍生物的合成、晶体结构及杀菌活性测定;(Ⅱ)：光学活性的N-取代吡咯烷甲醇衍生物的合成、晶体结构及杀虫活性测定</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=尹安琴&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 尹安琴</a> <span> . 2009</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120112268988.html">一类含二芳基硼和二芳基胺的Ullazine衍生物及其合成方法</a> <b>[P]</b> . <span> 中国专利： CN112279851A </span> <span> . 2021-01-29</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/061203768543.html">含三取代三聚氯氰的萘酰亚胺类衍生物及其合成方法和应用</a> <b>[P]</b> . <span> 中国专利： CN109020951B </span> <span> . 2020.06.02</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130400610091.html">4--3--5--6-4--2--3--2- VLCFA / HERBICIDAL COMPOSITIONS COMPRISING 4-AMINO-3-CHLORO-5-FLUORO-6-4-CHLORO-2-FLUORO-3-METHOXPHENYLPYRIDINE-2-CARBOXYLIC ACID OR A DERIVATIVE THEREOF AND VLCFA SYNTHESIS AND FATTY ACID/LIPID SYNTHESIS INHIBITING HERBICIDES</a> <b>[P]</b> . <span> 外国专利：  KR102118567B1 </span> <span> . 2020-06-03</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：4--3--5--6-4--2--3--2-VLCFA /包含4-AMINO-3-CHLORO-5-FLUORO-6-4-CHLORO-2-FLUORO-3的除草剂-间苯二酚-吡啶-2-羧酸或其衍生物和VLCFA合成及脂肪酸/脂类合成抑制除草剂 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130400292469.html">HERBICIDAL COMPOSITIONS COMPRISING 4-AMINO-3-CHLORO-5-FLUORO-6-(4-CHLORO-2-FLUORO-3-METHOXPHENYL)PYRIDINE-2-CARBOXYLIC ACID OR A DERIVATIVE THEREOF AND VLCFA SYNTHESIS AND FATTY ACID/LIPID SYNTHESIS INHIBITING HERBICIDES</a> <b>[P]</b> . <span> 外国专利：  KR1021185670000B1 </span> <span> . 2020.06.03</span> </div> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130403899850.html">Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid or a derivative thereof and vlcfa synthesis and fatty acid/lipid synthesis inhibiting herbicides</a> <b>[P]</b> . <span> 外国专利：  IL236854A </span> <span> . 2019-07-31</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：包含4-氨基-3-氯-5-氟-6-（4-氯-2-氟-3-甲氧基苯基）吡啶-2-羧酸或其衍生物和vlcfa合成和抑制脂肪酸/脂质合成的除草组合物除草剂 </span> </p> </li> </ul> </div> </div> </div> <div class="theme cardcommon" style="overflow: auto;display:none"> <h3 class="all_title" id="enpatent55">相关主题</h3> <ul id="subject"> </ul> </div> </div> </div> </div> <div class="right rightcon"> <div class="details_img cardcommon clearfix" style="margin-bottom: 10px;display:none;" > </div> </div> </div> <div id="thesis_get_original1" class="downloadBth" style="bottom: 19px;z-index: 999;" onclick="ywcd('0704022773794','4',7,2,1,'',this,24)" class="delivery" prompt="010401" title="通过人工服务将文献原文发送至邮箱" >获取原文</div> <div class="journalsub-pop-up" style="display: none"> <div class="journal-sub"> 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