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Issue 2, 2015
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Mixed non-covalent assemblies of ethynyl nile red and ethynyl pyrene along oligonucleotide templates

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Abstract

Ethynyl pyrene and ethynyl nile red as modifications at the 5-position of 2′-deoxyuridines self-assemble non-covalently and specifically along oligo-2′-deoxyadenosines as templates. Oligo-2′-deoxyadenosines of the lengths (dA)10–(dA)20 are able to retain nearly exactly as many ethynyl nile red units in solution as binding sites are available on these templates. In contrast, in the presence of oligo-2′-thymidines the ethynyl nile red moieties are similarly insoluble to those in the absence of any oligonucleotide and yield an aggregate. The mixed assemblies of both chromophores are highly ordered, show left-handed chirality and yield dual fluorescence. The strong excitonic coupling indicates assemblies with a high degree of order. These results show that DNA represents an important supramolecular scaffold for the templated, helical and non-covalent arrangement not only for one type of chromophore but also for mixtures of two different chromophores.

Graphical abstract: Mixed non-covalent assemblies of ethynyl nile red and ethynyl pyrene along oligonucleotide templates

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Publication details

The article was received on 31 Aug 2014, accepted on 16 Oct 2014 and first published on 17 Oct 2014


Article type: Paper
DOI: 10.1039/C4OB01860E
Citation: Org. Biomol. Chem., 2015,13, 487-492
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    Mixed non-covalent assemblies of ethynyl nile red and ethynyl pyrene along oligonucleotide templates

    P. Ensslen, Y. Fritz and H. Wagenknecht, Org. Biomol. Chem., 2015, 13, 487
    DOI: 10.1039/C4OB01860E

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