DNA-templated assembly of naphthalenediimide arrays

Abstract

π-Stacked naphthalenediimide (NDI) arrays are of interest as charge-transport materials. We have designed and synthesized an NDI derivative with two ZnII-cyclens that act as receptors for the thymine base in DNA. UV/Vis and CD spectroscopy, gel filtration, and molecular-modeling studies have shown that the bis(ZnII-cyclen)-NDI can be assembled in the presence of oligo-dT to form π-stacked NDI arrays. The assembly of the NDI arrays was found to be dependent on the length of the oligo-dT and the temperature. The NDI-oligo-dT assembly on a gold substrate exhibits photocurrent responses due to electron transfer through the π-stacked array. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.