Does a Cyclopropane Ring Enhance the Electronic Communication in Dumbbell-Type C60 Dimers?

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• 作者：Andrea La Rosa ; Katalin Gillemot ; Edmund Leary ; Charalambos Evangeli ; Mar铆a Teresa Gonz谩lez ; Salvatore Filippone ; Gabino Rubio-Bollinger ; Nicol谩s Agra茂t ; Colin J. Lambert ; Nazario Mart铆n
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：June 6, 2014
• 年：2014
• 卷：79
• 期：11
• 页码：4871-4877
• 全文大小：450K
• 年卷期：v.79,no.11(June 6, 2014)
• ISSN：1520-6904

文摘

Two C₆₀ dumbbell molecules have been synthesized containing either cyclopropane or pyrrolidine rings connecting two fullerenes to a central fluorene core. A combination of spectroscopic techniques reveals that the cyclopropane dumbbell possesses better electronic communication between the fullerenes and the fluorene. This observation is underpinned by DFT transport calculations, which show that the cyclopropane dumbbell gives a higher calculated single-molecule conductance, a result of an energetically lower-lying LUMO level that extends deeper into the backbone. This strengthens the idea that cyclopropane behaves as a quasi-double bond.