Helical Nanographenes Containing an Azulene Unit: Synthesis, Crystal Structures, and Properties

摘要

Abstract > Three unprecedented helical nanographenes ( 1 , 2 , and 3 ) containing an azulene unit are synthesized. The resultant helical structures are unambiguously confirmed by X‐ray crystallographic analysis. The embedded azulene unit in 2 possesses a record‐high twisting degree (16.1°) as a result of the contiguous steric repulsion at the helical inner rim. Structural analysis in combination with theoretical calculations reveals that these helical nanographenes manifest a global aromatic structure, while the inner azulene unit exhibits weak antiaromatic character. Furthermore, UV/Vis‐spectral measurements reveal that superhelicenes 2 and 3 possess narrow energy gaps ( 2 : 1.88?eV; 3 : 2.03?eV), as corroborated by cyclic voltammetry and supported by density functional theory (DFT) calculations. The stable oxidized and reduced states of 2 and 3 are characterized by in‐situ EPR/Vis–NIR spectroelectrochemistry. Our study provides a novel synthetic strategy for helical nanographenes containing azulene units as well as their associated structures and physical properties. </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> > 三个前所未有的螺旋纳米（ 1 </ b> 那 2 </ b> ，和 3 </ b> 合成含有氮素单元。由X射线结晶分析明确证实所得螺旋结构。嵌入的氮素单位 2 </ b> 由于螺旋内边缘处的连续空间排斥而具有记录高扭曲度（16.1°）。结构分析与理论计算的组合揭示了这些螺旋纳米表现出全局芳族结构，而内亚祖烯单元表现出弱的抗半导体特征。此外，UV / Vis光谱测量揭示了超咯 2 </ b> 和 3 </ b> 具有狭窄的能量差距（ 2 </ b> ：1.88？ev; 3 </ b> ：2.03？EV），通过循环伏安法证实并由密度泛函理论（DFT）计算支持。稳定的氧化和减少状态 2 </ b> 和 3 </ b> 以原位EPR / Vis-nir光谱电化学为特征。我们的研究提供了一种新的合成策略，可用于含有茉莉单位的螺旋纳米，以及它们相关的结构和物理性质。 </ 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14期</span><b style="margin: 0 2px;">|</b><span>共6页</span> </div> </li> <li> <div class="author"> <span class="lefttit">作者</span> <p id="fAuthorthree" class="threelineshidden zhankaihshouqi"> </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"> </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=azulene&option=203" rel="nofollow">azulene;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=helicenes&option=203" rel="nofollow">helicenes;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=nanographenes&option=203" rel="nofollow">nanographenes;</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> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Scholl reaction&option=203" rel="nofollow">Scholl reaction;</a> </p> <div class="translation"> 机译：亚祖琳;直升机;nanographenes;多环芳烃;Scholl反应; 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