Theoretical Study of the Diels-Alder Dimerization of C₃₀H₁₀

Abstract

The development of new techniques for the synthesis of fullerenes is needed to reduce the production cost and the availability of those materials.[1-10] In this work we study, using the density functional theory (DFT) and the nudge elastic band (NEB) method, a route to obtain the C60 from two pentacyclopentacorannulene C30H10 fragments. The accessible precursor of C60, is a C60H20 molecule, which is a C60 fullerene wrapped by a double belt of twenty H atoms forming C-H bonds around the equatorial plane of C60 (the poles are occupied by the central pentagons of the two fragments). The proposed C60H20 molecule has a synthetic analogue reported by Boltalina et al.[11] Our theoretical justification for the dimerization of the C30H10 fragments supports the achievable synthetic route for the C60.[12] References. 1.- Diederich, Y. Rubin, Angew. Chem. Int. Ed., 1992, 31, 1101. 2.- T. Scott, Angew. Chem. Int. Ed., 2004, 43, 4994. 3.- M. Tsefrikas, L. T. Scott, Chem. Rev., 2006, 106, 4868. 4.- Mojica, F., J. A. Alonso, J. Phys. Org. Chem., 2013, 26, 526. 5.- T. Scott, M. M. Boorum, B. J. McMahon, S. Hagen, J. Mack, J. Blank, H. Wegner, A. de Meijere, Science, 2002, 295, 1500. 6.- Otero, G. Biddau, C. Sánchez-Sánchez, R. Caillard, M. F. López, C. Rogero, F. J. Palomares, N. Cabello, M. A. Basanta, J. Ortega, J. Méndez, A. M. Echavarren, R. Pérez, B. Gómez-Lor, J. A. Martín-Gago, Nature, 2008, 454, 865. 7.- B. M. Ansems, L. T. Scott, J. Am. Chem. Soc., 2000, 122, 2719. 8.- H. F. Bunz, Y. Rubin, Y. Tobe, Chem. Soc. Rev., 1999, 28,107. 9.- L. Chapman, M. R. Engel, J. P. Springer, J. C. Clardy, J. Am. Chem. Soc., 1971, 93, 6696 10.- T. Scott, M. A. Petrukhina, Preface in Fragments of Fullerenes and Carbon Nanotubes: Designed Synthesis, Unusual Reactions and Coordination Chemistry; L. T. Scott, M. A. Petrukhina, Eds.; John Wiley & Sons Inc., Hoboken, New Jersey, 2012, pp. vii–x. 11.- V. Boltalina, V. Yu. Markov, P. A. Troshin, A. D. Darwish, J. M. Street, and R. Taylor, Angew. Chem. Int. Ed., 2001, 40, 787. 12.- A. Richaud, M. J. López, M. Mojica, J. A. Alonso, F. Méndez. RSC Adv., 2020, 10, 3689-3693. https://doi.org/10.1039/C9RA09804F.