Ethynyl and Ethenyl Ferrocenyl Dyads with Acridine, Acridone, and Anthraquinone

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• 作者：Elise M. McGale ; Brian H. Robinson ; and Jim Simpson
• 刊名：Organometallics
• 出版年：2003
• 出版时间：March 3, 2003
• 年：2003
• 卷：22
• 期：5
• 页码：931 - 939
• 全文大小：227K
• 年卷期：v.22,no.5(March 3, 2003)
• ISSN：1520-6041

文摘

Ethynylferrocenyl derivatives of 2,7-acridine (1, 2), 9-N-acridone (4), and 2-anthraquinone(6) are described. (Z)-10-(2-iodo-1-ethenylferrocene)-9(10H)-acridinone (3), an intermediatein the formation of 4, N-Fc(CH₂)_n-acridone (5; n = 8, 11), 1-Fc-anthraquinone (7), and (E)-(2-FcC=C)-anthraquinone (8) were also investigated. The X-ray structures of 3 and 6 weredetermined. B3LYP calculations, UV/vis spectroelectrochemistry, cyclic voltammetry, andESR spectra were used to probe the ground and excited states of both the neutral and oxidizedcompounds. Emission is observed from oxidized, but not neutral, 4 and 6; however, 1, 2,and 8 are fluorescent. Surprisingly, emission is reduced upon oxidation of 2 and 8, whichappears to correlate with the greater distortion in the excited compared to ground states.