Issue 30, 2012

Double stranded polymeric ladderphanes with 16-π-electron antiaromatic metallocycle linkers

Abstract

Three double stranded polymeric ladderphanes with 16-π-electron antiaromatic metallocycle linkers are synthesised by ring opening metathesis polymerisation of the corresponding bisnorbornene monomers. Scanning tunnelling microscopic (STM) images indicate that these polymers can assemble nicely on a graphite surface to form a highly ordered pattern which has been observed in other ladderphanes with different kinds of aromatic linkers. Little change in 1H NMR, absorption spectra and electrochemical oxidation potential between these polymers and the corresponding monomers suggest that there would be no interactions between adjacent antiaromatic linkers in these polymeric ladderphanes. Presumably, the distance between two antiaromatic rings in these ladderphanes (5–6 Å) is far too long in comparison with that between two rings in methylene-bridged antiaromatic superphanes (2.5 Å<), where stabilisation is predicted by theoretical calculations.

Graphical abstract: Double stranded polymeric ladderphanes with 16-π-electron antiaromatic metallocycle linkers

Supplementary files

Article information

Article type
Paper
Submitted
15 yan 2012
Accepted
20 fev 2012
First published
21 fev 2012

Org. Biomol. Chem., 2012,10, 5948-5953

Double stranded polymeric ladderphanes with 16-π-electron antiaromatic metallocycle linkers

H. Huang, C. Chao, S. Lee, H. Wu, C. Chen and T. Luh, Org. Biomol. Chem., 2012, 10, 5948 DOI: 10.1039/C2OB25114K

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