Chapter 12. Synthesis and Chemistry of Polycyclic Aromatic Hydrocarbons with Curved Surfaces: Buckybowls

  1. Prof. Michael M. Haley2 and
  2. Prof. Rik R. Tykwinski3
  1. Andrzej Sygula and
  2. Peter W. Rabideau

Published Online: 13 JUN 2006

DOI: 10.1002/3527607994.ch12

Carbon-Rich Compounds: From Molecules to Materials

Carbon-Rich Compounds: From Molecules to Materials

How to Cite

Sygula, A. and Rabideau, P. W. (2006) Synthesis and Chemistry of Polycyclic Aromatic Hydrocarbons with Curved Surfaces: Buckybowls, in Carbon-Rich Compounds: From Molecules to Materials (eds M. M. Haley and R. R. Tykwinski), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, FRG. doi: 10.1002/3527607994.ch12

Editor Information

  1. 2

    Department of Chemistry, University of Oregon, Eugene, Oregon 97403-1253, USA

  2. 3

    Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada

Author Information

  1. Department of Chemistry, Mississippi State University, Mississippi State, MS 39762-9573, USA

Publication History

  1. Published Online: 13 JUN 2006
  2. Published Print: 6 FEB 2006

ISBN Information

Print ISBN: 9783527312245

Online ISBN: 9783527607990

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Keywords:

  • buckybowls;
  • polycyclic aromatic hydrocarbons with curved surfaces;
  • synthesis;
  • chemistry;
  • corannulene;
  • C60;
  • organometallic derivatives of buckybowls

Summary

This chapter contains sections titled:

  • Introduction

  • Synthesis of Buckybowls

    • Corannulene: A Synthetic Travel from “Wet” Chemistry …

    • … to Flash Vacuum Pyrolysis …

    • … and Back

    • Practical Synthesis of Corannulene by Intramolecular Carbenoid Coupling of Dibromomethyl Groups

    • Beyond Corannulene

      • On the Surface of C60

      • Molecular Architectures with Corannulene Scaffolds

      • Large Systems with Corannulene Fragments

  • Bowl-to Bowl Inversion in Buckybowls

  • Organometallic Derivatives of Buckybowls

    • Alkali Metal Reduction

    • Transition Metal Complexes

  • Conclusions

  • Experimental: Selected Procedures

    • Preparation of Octabromide 11 from 10

    • Preparation of Corannulene from 11 by Low-valent Vanadium Coupling

    • Preparation of Tetrabromocorannulene from 11 by Carbenoid Coupling

    • Preparation of 43 by Double Diels–Alder Reaction

    • Preparation of 44 by Aluminum Cyclohexoxide Reduction of 43

    • Preparation of 45

    • Preparation of Dodecabromide 46

    • Preparation of Dicorannulenobarrelene 47