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Crystal design using multipolar electrostatic interactions: A concept study for organic electronics.

Peer Kirsch1, Qiong Tong1, Harald Untenecker1

  • 1Merck KGaA, Liquid Crystal R&D Chemistry, Frankfurter Str. 250, D-64392 Darmstadt, Germany, Tel: (+49)6151-72-41118.

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|December 25, 2013
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Summary
This summary is machine-generated.

New heterohexacene analogues with quadrupolar charges are synthesized. Their unique brickwork crystal packing enables more isotropic charge transport, beneficial for organic semiconductors.

Keywords:
aromatic stackingcharge carrier transportcrystal designelectrostatic controlorganic semiconductororgano-fluorine

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Solid-State Physics

Background:

  • Acenes are a class of organic compounds with potential applications in organic electronics.
  • Traditional acene packing, such as herringbone, can limit charge transport efficiency.
  • Controlling molecular packing is crucial for optimizing semiconductor performance.

Purpose of the Study:

  • To synthesize novel heterohexacene analogues with specific charge distributions.
  • To investigate the crystallization behavior and packing motifs of these analogues.
  • To evaluate the impact of molecular packing on charge transport properties.

Main Methods:

  • A straightforward synthetic protocol was employed for heterohexacene analogue synthesis.
  • X-ray crystallography was used to determine the solid-state structures and packing arrangements.
  • Charge transport properties were assessed based on the observed crystal packing.

Main Results:

  • Heterohexacene analogues with a quadrupolar charge distribution were successfully synthesized.
  • These compounds exhibit a slipped-stack, brickwork-like crystal packing, distinct from typical acenes.
  • Electrostatic interactions were identified as the primary driver for this unique packing.
  • The brickwork packing facilitates more isotropic charge transport compared to herringbone motifs.

Conclusions:

  • Simple synthesis provides access to heterohexacene analogues with tunable electronic properties.
  • The quadrupolar charge distribution promotes a brickwork packing, enhancing charge mobility.
  • This finding offers a new strategy for designing high-performance organic semiconductor materials.