Ferrocene-linked thymine/uracil conjugates: base pairing directed self-assembly and supramolecular packing.
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.
Patwa
Amit N
AN
Division of Organic Synthesis, National Chemical Laboratory, Pune 411008, India.
Gupta
Susmita
S
Gonnade
Rajesh G
RG
Kumar
Vaijayanti A
VA
Bhadbhade
Mohan M
MM
Ganesh
Krishna N
KN
D020029:Base Pairing; D018360:Crystallography, X-Ray; D005296:Ferrous Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D000075163:Metallocenes; D015394:Molecular Structure; D013055:Spectrophotometry, Infrared; D013941:Thymine / Q000737:chemistry*; D014498:Uracil / Q000737:chemistry*
D005296:Ferrous Compounds; D000075163:Metallocenes; D014498:Uracil; D013941:Thymine; C004998:ferrocene