Mobius aromaticity in N-fused [24]pentaphyrin upon Rh(I) metalation
Mobius aromaticity in N-fused [24]pentaphyrin upon Rh(I) metalation
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DOI：
10.1021/ja7100483
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发表时间：
2008-02-13
影响因子：
15
通讯作者：
Kim, Dongho
中科院分区：
文献类型：
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作者：
Park, Jong Kang;Yoon, Zin Seok;Kim, Dongho
N-稠合五卟啉（NFP 5）是内消旋芳基五卟啉的稳定形式，是实现Huckel芳香性、非芳香性和Mobius芳香性的有趣平台，其芳香性取决于π电子数、内消旋取代基和金属化。值得注意的是，五（五氟苯基）取代的[24]NFPS的Rh（1）配合物已通过晶体结构，H-1 NMR光谱，NICS计算和双光子吸收（TPA）截面表征为Mobius芳香族大环。据我们所知，该系统是迄今为止最小的Mobius芳香分子，具有明显的diatropic环电流。这项工作表明了我们的合成策略对Mobius芳香分子的巨大潜力，以及可能使用TPA值作为芳香性的定量测量。
N-fused pentaphyrins (NFP5), stable forms of meso-aryl pentaphyrins, are interesting platforms to realize Huckel aromaticity, nonaromaticity and Mobius aromaticity depending upon the number of pi-electrons, meso-substituent, and metalation. Remarkably, Rh(1) complex of pentakis(pentafluorophenyl) substituted [24]NFPS has been characterized as a Mobius aromatic macrocycle by the crystal structure, H-1 NMR spectrum, NICS calculation, and two-photon absorption (TPA) cross section. This system is, to the best of our knowledge, the smallest Mobius aromatic molecule with a distinct diatropic ring current characterized so far. This work demonstrates the great potential of our synthetic strategy toward Mobius aromatic molecules as well as the possible use of TPA value as a quantitative measure of aromaticity.