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"Butterfly Wings" Stabilize Heptacene.

Matthias Müller1, Elias C Rüdiger1, Silke Koser1

  • 1Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 17, 2018
PubMed
Summary
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Researchers synthesized novel bisalkynylated heptacene and pentacene derivatives using Stille reactions. These triphenylene-winged polycyclic aromatic hydrocarbons exhibit remarkable stability and retain key electronic properties.

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Polycyclic Aromatic Hydrocarbons (PAHs)

Background:

  • Heptacenes and pentacenes are extended polycyclic aromatic hydrocarbons (PAHs) with unique electronic properties.
  • The synthesis and stabilization of larger PAHs like heptacenes remain challenging.
  • Functionalization of PAHs is crucial for tuning their optoelectronic characteristics.

Purpose of the Study:

  • To report the synthesis of novel bisalkynylated derivatives of tetrabenzo[a,c,p,r]heptacene and tetrabenzo[a,c,l,n]pentacene.
  • To investigate the stability and electronic properties of these functionalized extended PAHs.
  • To explore the utility of Stille coupling reactions for constructing complex PAH architectures.

Main Methods:

  • Employed two- and fourfold Stille coupling reactions.
Keywords:
X-ray diffractionacenesheptacenespi extensionstabilization through benzannulation

Related Experiment Videos

  • Utilized 9-stannafluorene as a key organotin reagent.
  • Reacted with suitable tetrabromoacene precursors to form the target molecules.

    • Main Results:

    • Successfully synthesized bisalkynylated derivatives of tetrabenzo[a,c,p,r]heptacene and tetrabenzo[a,c,l,n]pentacene.
    • The resulting triphenylene-winged heptacenes demonstrated surprising stability.
    • These derivatives maintained a significant portion of the intrinsic electronic properties of the parent heptacenes.

    Conclusions:

    • Stille reactions provide an effective route for synthesizing complex, functionalized extended PAHs.
    • The introduction of triphenylene wings enhances the stability of heptacene derivatives.
    • These stable, functionalized heptacenes hold potential for applications in organic electronics.