Annelated, Chiral π-Conjugated Systems: Tetraphenylenes and Helical β-Oligothiophenes

Abstract

Compounds with highly annelated, chiral π-systems, such as tetraphenylenes and [n]helicenes, are known to possess strong chiral properties and high configurational stability, which are prerequisites for many chiral materials. This account describes the unfolding story about our research on the synthesis and X-ray crystallographic characterization of functionalized nonracemic tetra­phenylenes and helical β-oligothiophenes, as well as related [n]helicene derivatives.

• 1 Introduction

• 1.1 Riley’s Three-Dimensional Graphite

• 1.2 Annelated Helical β-Oligothiophenes: Carbon-Sulfur [n]Helicenes

• 2 Tetraarylenes

• 2.1 Double Helical Octaphenylene

• 2.2 Biphenylene Dimer

• 2.3 Enantiopure Tetranaphthylene: Binaphthyl Dimer

• 2.4 Asymmetric Synthesis of Tetraphenylenes: Greek Cross Dodecaphenylene

• 3 Synthesis of Annelated Helical β-Oligothiophenes

• 3.1 [7]Helicene

• 3.2 [7]Helicene: McMurry Reaction

• 3.3 [11]Helicene

• 3.4 Toward [n]Helicenes with n >11: Progress Report

• 4 Discovery of Conjoined Double Helicenes

• 5 Future Directions

chirality - asymmetric synthesis - enantiomeric resolution - kinetic resolution - coupling

References and Notes

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