Chemistry of Hetera-buckybowl Trichalcogenasumanenes

Dedicated to Prof. Zhongli Liu on the occasion of his 80^th birthday

Abstract

Buckybowls attract significant attention in chemistry and materials science owing to their unique features related to both geometric and electronic aspects. Doping the π-skeleton of buckybowls with the main group elements results in hetera-buckybowls, and accordingly has a large influence on the chemical and physical properties. This account summarizes our research progress on hetera-buckybowl trichalcogenasumanenes (TCSs), including their synthesis, regioselective oxidations, transformation into various hetero polycycles (chiral π-systems, molecular spoons, etc.), and their application as optoelectronic materials.

1 Introduction

2 Synthesis of TCSs

3 Structural and Electronic Features of TCSs

4 Regioselective Oxidation of TCSs

4.1 Cleavage of the Edged Benzene Rings

4.2 Oxidation of the Thiophene Rings

4.3 Transformation of Butoxy Groups into an ortho-Quinone

4.4 Intermolecular Charge Transfer

4.5 Influence of Chalcogen Atoms on Oxidation Reactions

5 Synthesis of Hetero Polycycles from TCSs

6 Optoelectronic Properties of TCSs and Their Derivatives

7 Conclusion

Key words

conjugated polycycles - buckybowls - hetera-sumanenes - trichalcogenasumanenes - chiral π-systems - molecular spoons - regioselective oxidation - optoelectronic properties

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