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J Phys Chem A. 2017 Jan 19;121(2):523-531. doi: 10.1021/acs.jpca.6b10231. Epub 2017 Jan 5.

Theoretical Study on the Reactivity and Regioselectivity of the Diels-Alder Reaction of Fullerene: Effects of Charges and Encapsulated Lanthanum on the Bis-Functionalization of C70.

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Postdoctoral Research Base, School of Chemistry and Chemical Engineering, Henan Institute of Science and Technology , Xinxiang 453003, China.
Henan University of Technology , Zhengzhou 450001, China.
Key Laboratory of Theoretical and Computational Photochemistry, Ministry of Education, College of Chemistry, Beijing Normal University , Beijing 100875, China.


Bis-adducts of fullerenes are important for both material and biological science. The first added substituent greatly impacts the reactivity and regioselectivity of fullerene. What determines the bond reactivity and how to control the regioselectivity are two crucial questions in synthesizing bis-adduct of C70. Recently, an unexpected 12 o'clock isomer of anthracene bis-adduct of C70 was prepared with high yield by the Diels-Alder (DA) reaction although three possible isomers (12, 2, and 5 o'clock isomers) may be formed. In the current study, the beneath mechanism is systematically investigated by density functional theory methods. Moreover, effects of charges and encapsulated lanthanum atom on the regioselectivity are reported. The computational results successfully rationalize experimental observations by Venkata et al. A possible way to change the regioselectivity of DA reaction is put forward. The kinetical promotion effect of an encapsulated La atom on the 12 o'clock reaction is elucidated.


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