Successive Diels-Alder Cycloadditions of Cyclopentadiene to [10]CPP⊃C₆₀: A Computational Study.

ABSTRACT: Fullerenes have potential applications in many fields. To reach their full potential, fullerenes have to be functionalized. One of the most common reactions used to functionalize fullerenes is the Diels-Alder cycloaddition. In this case, it is important to control the regioselectivity of the cycloaddition during the formation of higher adducts. In C₆₀, successive Diels-Alder cycloadditions lead to the T_h-symmetric hexakisadduct. In this work, we explore computationally using density functional theory (DFT) how the presence of a [10]cycloparaphenylene ring encapsulating C₆₀ ([10]CPP⊃C₆₀) affects the regioselectivity of multiple additions to C₆₀. Our results show that the presence of the [10]CPP ring changes the preferred sites of cycloaddition compared to free C₆₀ and leads to the formation of the tetrakisadduct. Somewhat surprisingly, our calculations predict formation of this particular tetrakisadduct to be more favored in [10]CPP⊃C₆₀ than in free C₆₀.

SUBMITTER: Pareras G 

PROVIDER: S-EPMC9016765 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature