BN‐Embedded Polycyclic Aromatic Hydrocarbon Oligomers: Synthesis, Aromaticity, and Reactivity

Chen Yijing; Chen Weinan; Qiao Yanjun; Lu Xuefeng; Zhou Gang

摘要

Abstract >BN‐embedded oligomers with different pairs of BN units were synthesized by electrophilic borylation. Up to four pairs of BN units were incorporated in the large polycyclic aromatic hydrocarbons (PAHs). Their geometric, photophysical, electrochemical, and Lewis acidic properties were investigated by X‐ray crystallography, optical spectroscopy, and cyclic voltammetry. The B?N bonds show delocalized double‐bond characteristics and the conjugation can be extended through the trans‐orientated aromatic azaborine units. Calculations reveal the relatively lower aromaticity for the inner azaborine rings in the BN‐embedded PAH oligomers. The frontier orbitals of the longer oligomers are delocalized over the inner aromatic rings. Consequently, the inner moieties of the BN‐embedded PAH oligomers are more active than the outer parts. This is confirmed by a simple oxidation reaction, which has significant effects on the aromaticity and the intramolecular charge‐transfer interactions. </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> 用电泳促进硼酸化合成具有不同成对的BN单元的BN嵌入的低聚物。在大的多环芳烃（PAH）中掺入了最多四对BN单元。通过X射线晶体学，光学光谱学和循环伏安法研究了它们的几何，光药，电化学和路易斯酸性特性。 B？N键显示分层的双键特性，并且可以通过横型芳族氮杂硼胺单元延伸缀合。计算揭示了BN嵌入式PAH低聚物中内氮杂环环的相对较低的芳香性。较长低聚物的前轨道在内芳环上划分。因此，BN嵌入式PAH低聚物的内部部分比外部部分更有效。这是通过简单的氧化反应来证实，这对芳香性和分子内电荷转移相互作用具有显着影响。</ 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-19011/'>《Angewandte Chemie》</a> <b style="margin: 0 2px;">|</b><span>2020年第18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=Chen Yijing&option=202" target="_blank" rel="nofollow">Chen Yijing;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Chen Weinan&option=202" target="_blank" rel="nofollow">Chen Weinan;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Qiao Yanjun&option=202" target="_blank" rel="nofollow">Qiao Yanjun;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Lu Xuefeng&option=202" target="_blank" rel="nofollow">Lu Xuefeng;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhou Gang&option=202" target="_blank" rel="nofollow">Zhou Gang;</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>Lab of Advanced MaterialsFudan UniversityShanghai 200438 P. R. China;</p> <p>Lab of Advanced MaterialsFudan UniversityShanghai 200438 P. R. China;</p> <p>Department of Materials ScienceFudan UniversityShanghai 200438 P. R. China;</p> <p>Department of Materials ScienceFudan UniversityShanghai 200438 P. R. China;</p> <p>Lab of Advanced MaterialsFudan UniversityShanghai 200438 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/1188.html" title="应用化学">应用化学;</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=aromaticity&option=203" rel="nofollow">aromaticity;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=azaborine&option=203" rel="nofollow">azaborine;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=heterocycles&option=203" rel="nofollow">heterocycles;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=oligomers&option=203" rel="nofollow">oligomers;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=polycyclic aromatic hydrocarbons&option=203" rel="nofollow">polycyclic aromatic hydrocarbons;</a> </p> <div class="translation"> 机译：芳香;氮杂曲调;杂环;低聚物;多环芳烃; </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/0704028161877.html">BN‐Embedded Polycyclic Aromatic Hydrocarbon Oligomers: Synthesis, Aromaticity, and Reactivity</a> <b>[J]</b> . 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