The five nucleobases foster nucleic acid self-assembly. Since this process occurs on a molecular scale, it suggests potential applications in nanotechnology. The question of self-assembly of hybrid nucleobases was explored computationally with compounds that had complementary head-tail interactions. Hydrogen and halogen bonding were explored for their potential contributions to association. Because graphene is the ultimate polynuclear aromatic hydrocarbon, and provides the possibility for ?-? interactions similar to those found in DNA, it was chosen as a matrix for self-assembly. Bonding a hydrid nucleobase to the graphene surface by means of reaction with an azomethine ylide (1) to initiate assembly was also considered (2). Calculations were performed with DMol3 using model supercells to represent graphene. Rather large supercells are required (7x7x1 in the figure.) The planarity of this graphene model is distorted by the presence of the hydrogen bonded hybrid nucelobases. Corrections for BSSE and dispersion interactions were incorporated.(1) See (a) Banks, H.D. Org. Biomol. Chem. 2011  , 6335. (b) Banks, H.D. J. Org. Chem. 2010  , 75, 2510 and references cited therein.(2) Cao, Y.; Houk, K.N. J. Mater. Chem. 2011  , 21, 1503.

Can graphene promote the self-assembly of hybrid nucleobases?

243rd National Meeting (2012)

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