Detail publikace

Implementation of polycyclic cycloalkane systems: a path to highperforming, soluble, versatile and sustainable organic semiconducting materials

KOVALENKO, A.YUMASAK, C. HEINRICHOVÁ, P. STŘÍTESKÝ, S. VALA, M. WEITER, M. SARICIFCI N.S. KRAJČOVIČ, J.

Originální název

Implementation of polycyclic cycloalkane systems: a path to highperforming, soluble, versatile and sustainable organic semiconducting materials

Typ

abstrakt

Jazyk

angličtina

Originální abstrakt

Soluble organic semiconducting materials have a particular application potential for easily processed lowcost organic electronics devices. Solubility of organic pi-conjugated small molecule derivatives, such as diketopyrrolopyrroles (DPPs), indigos, epindolidiones, squaraines and many other, is usually attained by a sidechain alkyl substitution, which is meant to interrupt inter- and intramolecular H-bonds. Due to these bonds insoluble organic semiconducting materials are usually more stable; moreover as a result of tight aggregation of -conjugated cores through intermolecular H-bond insoluble materials have shown remarkable thermal stability as well as high charge carrier mobilities for both electrons and holes [1]. However insolubility brings its obverse case: such materials are difficult to purify and they can’t be deposited by coating or printing techniques, which is a promising way towards cheap production organic electronics. In this work, we offer a strategy to synthesize thermally stable and soluble high-performing materials for a wide range of organic electronics applications. The crucial component of the present approach is using adamantyl substitutions in solubilization side-groups. Ability of adamantane molecule to self-organize into crystals with unusually high melting point was used to reinforce packing of -conjugated dyes in the solid state. As a result materials with adamantyl containing sidechains possess superior electrical and optical properties, and at the same time high thermal stability. Abovementioned side chain can improve solid-state fluorescence quantum yields of the materials [2] and significantly increase the melting point. Considering electrical properties, soluble DPP derivative with ethyl-adamantyl solubilization side-groups showed abmipolar behavior with both hole and electron mobilities higher than the insoluble analogue. How it was confirmed by XRD analysis a distance between - conjugated cores is shorted than the one of insoluble material due to adamantyl-adamantyl aggregations, which resulted in high charge carrier mobilities. It has to be added that this approach can be applied for a large portfolio of the organic dyes (indigos, epindolidiones, squaraines, oligothiophenes etc.), where solubility can be reached by a side-group substitution [3].

Klíčová slova

diketopyrrolopyrroles, ethyl-adamantyl, charge carrier mobilities

Autoři

KOVALENKO, A.;YUMASAK, C.; HEINRICHOVÁ, P.; STŘÍTESKÝ, S.; VALA, M.; WEITER, M.; SARICIFCI N.S.; KRAJČOVIČ, J.

Vydáno

12. 9. 2018

Nakladatel

Vysoké učení technické v Brně, Fakulta chemická

Místo

Purkyňova 464/118, 612 00 Brno

ISBN

978-80-214-5488-0

Kniha

7th Meeting on Chemistry and Life 2018. Book of abstracts

Číslo edice

první

Strany od

93

Strany do

93

Strany počet

1

BibTex

@misc{BUT156095,
  author="KOVALENKO, A. and YUMASAK, C. and HEINRICHOVÁ, P. and STŘÍTESKÝ, S. and VALA, M. and WEITER, M. and SARICIFCI N.S. and KRAJČOVIČ, J.",
  title="Implementation of polycyclic cycloalkane systems: a path to highperforming,
soluble, versatile and sustainable organic
semiconducting materials",
  booktitle="7th Meeting on Chemistry and Life 2018. Book of abstracts",
  year="2018",
  edition="první",
  pages="93--93",
  publisher="Vysoké učení technické v Brně, Fakulta chemická",
  address="Purkyňova 464/118, 612 00 Brno",
  isbn="978-80-214-5488-0",
  note="abstract"
}