5,14-二芳基二茚并[2,1-f:1',2'-j]并四苯：一种具有部分双自由基特征的新型稳定[7]螺旋烯。
5,14-Diaryldiindeno[2,1- f:1',2' -j]picene: A New Stable [7]Helicene with a Partial Biradical Character.
作者信息
Hsieh Ya-Chu, Wu Cheng-Feng, Chen Yi-Ting, Fang Chia-Te, Wang Chi-Shin, Li Chia-Hsin, Chen Liang-Yu, Cheng Mu-Jeng, Chueh Chu-Chen, Chou Pi-Tai, Wu Yao-Ting
机构信息
Department of Chemistry , National Cheng Kung University , 70101 Tainan , Taiwan.
出版信息
J Am Chem Soc. 2018 Oct 31;140(43):14357-14366. doi: 10.1021/jacs.8b08840. Epub 2018 Oct 22.
5,14-Diaryldiindeno[2,1- f:1',2' -j]picene (DDP, 1), a thermally and chemically stable helical arene, can be prepared from 1,4-bis[2-(arylethynyl)phenyl]benzene in four synthetic steps. Its helical backbone, which incorporates an o-quinodimethane moiety, was verified by X-ray crystallography, and this structural feature results in a very high barrier to racemization (exceeding 50 kcal/mol). DDP possesses versatile and promising properties, including a small HOMO-LUMO energy gap (1.31 eV for the dimesityl-substituted derivative 1ab), an electron spin resonance (ESR)-active character, a small triplet-singlet energy gap (4.75 kcal/mol), broad photoabsorption covering the ultraviolet, visible, and near-infrared (NIR) regions, two-photon absorption in the NIR range, and respectable ambipolar charge-transport behavior in a solution-processed organic field-effect transistor.
5,14-二芳基二茚并[2,1-f:1',2'-j]并苯（DDP，1）是一种热稳定且化学稳定的螺旋芳烃，可通过四个合成步骤由1,4-双[2-（芳基乙炔基）苯基]苯制备而成。其螺旋主链包含一个邻醌二甲烷部分，已通过X射线晶体学得到验证，并且这种结构特征导致了非常高的外消旋化能垒（超过50千卡/摩尔）。DDP具有多种有前景的特性，包括较小的最高占据分子轨道（HOMO）-最低未占据分子轨道（LUMO）能隙（对于二甲基取代衍生物1ab为1.31电子伏特）、电子自旋共振（ESR）活性特征、较小的三线态-单线态能隙（4.75千卡/摩尔）、覆盖紫外、可见和近红外（NIR）区域的宽光吸收、近红外范围内的双光子吸收以及在溶液处理的有机场效应晶体管中可观的双极性电荷传输行为。
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