当前位置：
X-MOL 学术
›
J. Am. Chem. Soc.
›
论文详情
Our official English website, www.x-mol.net, welcomes your
feedback! (Note: you will need to create a separate account there.)
[1,4]Diazocine-Embedded Electron-Rich Nanographenes with Cooperatively Dynamic Skeletons
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2023-02-16 , DOI: 10.1021/jacs.2c13823 Fuwei Gan 1 , Chengshuo Shen 2 , Wenying Cui 2 , Huibin Qiu 1
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2023-02-16 , DOI: 10.1021/jacs.2c13823 Fuwei Gan 1 , Chengshuo Shen 2 , Wenying Cui 2 , Huibin Qiu 1
Affiliation
|
Curved nanographenes (NGs) are emerging as promising candidates for organic optoelectronics, supramolecular materials, and biological applications. Here we report a distinctive type of curved NGs bearing a [1,4]diazocine core that is fused with four pentagonal rings. This is formed by Scholl-type cyclization of two adjacent carbazole moieties through an unusual diradical cation mechanism followed by C–H arylation. Owing to the strain in the unique 5–5–8–5–5-membered ring skeleton, the resulting NG adopts an interesting concave–convex cooperatively dynamic structure. By peripheral π-extension, a helicene moiety with fixed helical chirality can be further mounted to modulate the vibration of the concave–convex structure, through which the distant bay region of the curved NG inherits the chirality of the helicene moiety in a reversed fashion. The [1,4]diazocine-embedded NGs show typical electron-rich characteristics and form charge transfer complexes with tunable emissions with a series of electron acceptors. The relatively protruding armchair edge also allows the fusion of three NGs into a C2 symmetric triple diaza[7]helicene which reveals a subtle balance of fixed and dynamic chirality.
中文翻译：
[1,4]具有协同动态骨架的重氮辛嵌入富电子纳米石墨烯
弯曲的纳米石墨烯 (NG) 正在成为有机光电子学、超分子材料和生物应用的有前途的候选者。在这里，我们报告了一种独特类型的弯曲 NG，其带有 [1,4] 重氮辛核，该核与四个五角环融合。这是通过一个不寻常的双自由基阳离子机制，然后是 C-H 芳基化，通过两个相邻的咔唑部分的 Scholl 型环化形成的。由于独特的 5-5-8-5-5 元环骨架中的应变，由此产生的 NG 采用有趣的凹凸协同动态结构。通过外围π延伸，可以进一步安装具有固定螺旋手性的螺旋烯部分来调制凹凸结构的振动，通过该凹凸结构，弯曲NG的远湾区域以相反的方式继承了螺旋烯部分的手性。[1, 4]重氮辛嵌入的 NG 显示出典型的富电子特性，并与一系列电子受体形成具有可调发射的电荷转移络合物。相对突出的扶手椅边缘也让三个NG融合成一个C 2对称三重二氮杂[7]螺旋烯揭示了固定和动态手性的微妙平衡。
更新日期：2023-02-16
中文翻译：
[1,4]具有协同动态骨架的重氮辛嵌入富电子纳米石墨烯
弯曲的纳米石墨烯 (NG) 正在成为有机光电子学、超分子材料和生物应用的有前途的候选者。在这里，我们报告了一种独特类型的弯曲 NG，其带有 [1,4] 重氮辛核，该核与四个五角环融合。这是通过一个不寻常的双自由基阳离子机制，然后是 C-H 芳基化，通过两个相邻的咔唑部分的 Scholl 型环化形成的。由于独特的 5-5-8-5-5 元环骨架中的应变，由此产生的 NG 采用有趣的凹凸协同动态结构。通过外围π延伸，可以进一步安装具有固定螺旋手性的螺旋烯部分来调制凹凸结构的振动，通过该凹凸结构，弯曲NG的远湾区域以相反的方式继承了螺旋烯部分的手性。[1, 4]重氮辛嵌入的 NG 显示出典型的富电子特性，并与一系列电子受体形成具有可调发射的电荷转移络合物。相对突出的扶手椅边缘也让三个NG融合成一个C 2对称三重二氮杂[7]螺旋烯揭示了固定和动态手性的微妙平衡。
京公网安备 11010802027423号