A stereogenic heteroatom-containing substituent as an inducer of chirality in the derivatives of thiophenes (mono, oligo, and poly), fullerenes C₆₀, and multiwalled nanotubes

GRAPHICAL ABSTRACT

Abstract

Synthetic procedures applied recently in our laboratory for the preparation of a new thiophene, fullerene C₆₀ and multiwalled carbon nanotube (MWCNT) derivatives functionalized with a substituent containing an achiral and/or a stereogenic heteroatom are reviewed. Polymerization reactions of selected optically active 2-(3′-thienyl)ethyl aryl(alkyl) sulfoxides and tert-butyl-[2-(3′-thienyl)ethyl]phenylphosphine oxide are also mentioned. Mechanistic and stereochemical aspects of the presented protocols are discussed.

Keywords:

• Mono and polythiophenes
• multiwalled carbon nanotubes (MWCNT)
• fullerene C₆₀ derivatives
• chirality
• polymerization

Acknowledgments

Authors would like to thank Professor Piotr Kielbasinski for helpful discussions during preparation of the manuscript.

Funding

The studies presented in this account were in part financially supported by the National Science Center fund awarded based on the decisions UMO-2011/01/M/ST5/05240, UMO-2011/03/B/ST5/03233 and UMO-2011/01/B/ST5/06664.