Ferrocene-linked thymine/uracil conjugates: base pairing directed self-assembly and supramolecular packing

Patwa, Amit N. ; Gupta, Susmita ; Gonnade, Rajesh G. ; Kumar, Vaijayanti A. ; Bhadbhade, Mohan M. ; Ganesh, Krishna N. (2008) Ferrocene-linked thymine/uracil conjugates: base pairing directed self-assembly and supramolecular packing Journal of Organic Chemistry, 73 (4). pp. 1508-1515. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo7023416

Related URL: http://dx.doi.org/10.1021/jo7023416

Abstract

Ferrocene-linked bis(nucleobase) (1a-c) and chimeric nucleobase (1d) conjugates have been synthesized from mono- and bis(hydroxybutyl)ferrocene 6 via Mitsunobu reaction as the key step. X-ray crystallographic studies of ferrocene bis(nucleobase) conjugates reveal two-dimensional supramolecular organizations of backbones through self-assembled Watson-Crick and reverse Watson-Crick type pairs. Ferrocene-bis(thymine) conjugate self-assembles by reverse Watson-Crick pairing, while the corresponding bis(uracil) conjugate self-assembles by alternating WC and reverse WC type pairing. Such continuous assemblies are not seen in monosubstituted ferrocene nucleobase conjugates which form only planar sheets. The results are interesting from the point of understanding and engineering supramolecular assemblies through rational design of base pairing patterns.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:10811
Deposited On:09 Nov 2010 04:48
Last Modified:31 May 2011 09:32

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