Chapter 3. All-benzenoid Polycyclic Aromatic Hydrocarbons: Synthesis, Self-assembly and Applications in Organic Electronics

  1. Prof. Michael M. Haley2 and
  2. Prof. Rik R. Tykwinski3
  1. Jishan Wu and
  2. Klaus Müllen

Published Online: 13 JUN 2006

DOI: 10.1002/3527607994.ch3

Carbon-Rich Compounds: From Molecules to Materials

Carbon-Rich Compounds: From Molecules to Materials

How to Cite

Wu, J. and Müllen, K. (2006) All-benzenoid Polycyclic Aromatic Hydrocarbons: Synthesis, Self-assembly and Applications in Organic Electronics, 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.ch3

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. Max-Planck-Institut für Polymerforschung, Ackermannweg 10, 55128 Mainz, Germany

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:

  • carbon-rich compounds;
  • all-benzenoid polycyclic aromatic hydrocarbons (PAHs);
  • synthesis;
  • self-assembly;
  • structural characterizations;
  • applications in organic electronics

Summary

This chapter contains sections titled:

  • A Brief Introduction to Polycyclic Aromatic Hydrocarbons

  • All-benzenoid PAHs – Synthesis, Structural Characterizations and Electronic Properties

    • Hexa-peri-hexabenzocoronene – An Old Story with New Discoveries

    • All-benzenoid Graphitic PAHs Larger than HBCs

    • PAHs with Varying Peripheries

    • “Superbenzene” Chemistry and Others

  • Self-assembly and Application of Columnar Liquid Crystals based on PBAHs

    • Columnar Superstructures in the Bulk State

    • Alignment on Substrates and Device Applications of Columnar Liquid Crystals

    • Controlled Self-assembly in Solution

    • Two-dimensional Crystals at the Solid/Liquid Interface

  • Conclusion

  • Experimental: Selected Procedures

    • Synthesis of hexa-peri-hexabenzocoronene 10 by Cu(II)-mediated oxidative cyclodehydrogenation – a general procedure to prepare unsubstituted graphitic molecules

    • Synthesis of hexakis(4-n-dodecylphenyl)-peri-hexabenzocoronene (HBC-PhC12) – a general synthetic method towards six-fold alkyl- and alkylphenyl-substituted HBCs

    • Functionalization of insoluble HBC building blocks 30–32 by Sonogashira coupling reactions. Synthesis of hexakis(1-dodecynylphenyl)-peri-hexabenzocoronene (34a) as a representative example

    • Synthesis of C96-C12 precursor 1,3,5-tris[3′,4′-di(4″-dodecylphenyl)-2′,5′-diphenylphenyl]benzene (44a) by Diels-Alder cycloaddition reaction – a representative procedure for the synthesis of branched oligophenylenes

    • Hydrogenation of hexakis-dodecyl-peri-hexabenzo-coronenes

    • Synthesis of HBC dimer 38 by Yamamoto coupling reaction