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Tetrasubstituted Peropyrenes Formed by Reductive Aromatization: Synthesis, Functionalization and Characterization.

Simon Werner1, Tobias Vollgraff1, Jörg Sundermeyer1

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Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 25, 2021
PubMed
Summary

Synthesized novel 1,3,8,10-tetrasubstituted peropyrenes using Zn-mediated reductive aromatization. These functionalized peropyrenes exhibit tunable optoelectronic properties, showing potential as hole transporting semiconductors.

Keywords:
crystallographycyclic voltammetryfluorescenceperopyrenesreductive aromatization

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photophysics

Background:

  • Peropyrenes are polycyclic aromatic hydrocarbons with interesting optoelectronic properties.
  • Functionalization of peropyrene backbone is crucial for tuning their properties.

Purpose of the Study:

  • To synthesize novel 1,3,8,10-tetrasubstituted peropyrenes.
  • To investigate the influence of substituents on their optoelectronic properties.
  • To evaluate their potential as semiconductors.

Main Methods:

  • Zn-mediated reductive aromatization of peropyrenequinone.
  • Transition metal-catalyzed cross-coupling reactions.
  • X-ray crystallography, UV-Vis, fluorescence spectroscopy, cyclic voltammetry, DFT, and TD-DFT calculations.

Main Results:

  • Effective synthesis of 1,3,8,10-tetrasubstituted peropyrenes with various functional groups (silylethers, pivaloyl, triflyl, phosphinite, aryl, alkynyl).
  • Tunable HOMO and LUMO energy levels observed across a 0.8 eV gap window.
  • Structure-property relationships established through experimental and computational methods.

Conclusions:

  • The developed synthetic routes provide versatile access to functionalized peropyrenes.
  • Substituent-controlled tuning of optoelectronic properties is feasible.
  • These peropyrenes are promising candidates for hole transporting semiconductor applications.