From Corannulene to Indacenopicene: Effect of Carbon Framework Topology on Aromaticity and Reduction Limits
From Corannulene to Indacenopicene: Effect of Carbon Framework Topology on Aromaticity and Reduction Limits
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从 Corannulene 到 Indacenopicene：碳骨架拓扑对芳香度和还原极限的影响
DOI：
10.1021/acs.organomet.6b00395
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发表时间：
2016
期刊：
影响因子：
2.8
通讯作者：
M. Petrukhina
中科院分区：
文献类型：
--
作者：
Sarah N Spisak;Jingbai Li;A. Rogachev;Zheng Wei;O. Papaianina;K. Amsharov;A. V. Rybalchenko;A. Goryunkov;M. Petrukhina
首次用理论和实验相结合的方法研究了碗状多环芳烃吲哚(C26H12，1)的电子结构、还原极限和配位能力。通过与C20H10，2的直接比较，揭示了碳骨架的拓扑结构和对称性变化对吲哚的电子性质和芳香性的影响。从理论上预测了1的两个还原步骤的可达性，并进行了实验验证。通过循环伏安法检测到两个可逆单电子还原过程，其形式还原电位分别为−1.92和−2.29 V vs FC+/0，证明了相应的单阴离子和双阴离子状态的稳定性。双还原吲哚的产物被分离出来，并进行了充分的表征。它们的X-射线衍射研究揭示了四核金属有机化合物的形成。
The electronic structure, reduction limits, and coordination abilities of a bowl-shaped polycyclic aromatic hydrocarbon, indacenopicene (C26H12, 1), have been investigated for the first time using a combination of theoretical and experimental tools. A direct comparison with the prototypical corannulene bowl (C20H10, 2) revealed the effects of carbon framework topology and symmetry change on the electronic properties and aromaticity of indacenopicene. The accessibility of two reduction steps for 1 was predicted theoretically and then confirmed experimentally. Two reversible one-electron reduction processes with the formal reduction potentials at −1.92 and −2.29 V vs Fc+/0 were detected by cyclic voltammetry measurements, demonstrating the stability of the corresponding mono- and dianionic states of 1. The products of the doubly reduced indacenopicene have been isolated as rubidium and cesium salts and fully characterized. Their X-ray diffraction study revealed the formation of tetranuclear organometallic b...
影响因子：
15
作者：
Seiders, TJ;Baldridge, KK;Siegel, JS
通讯作者：
Siegel, JS
影响因子：
8.6
作者：
Sarkar, Santanu;Moser, Matthew L.;Haddon, Robert C.
通讯作者：
Haddon, Robert C.