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

TitleFerrocene-linked thymine/uracil conjugates: base pairing directed self-assembly and supramolecular packing
Publication TypeJournal Article
Year of Publication2008
AuthorsPatwa, AN, Gupta, S, Gonnade, RG, Kumar, VA, Bhadbhade, MM, Ganesh, KN
JournalJournal of Organic Chemistry
Volume73
Issue4
Pagination1508-1515
Date PublishedFEB
Type of ArticleArticle
ISSN0022-3263
Abstract

Ferrocene-linked bis(nucleobase) (la-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.

DOI10.1021/jo7023416
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)4.785
Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry
Physical and Materials Chemistry