Publication detail

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.

Original Title

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

English Title

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

Type

abstract

Language

en

Original Abstract

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].

English abstract

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].

Keywords

diketopyrrolopyrroles, ethyl-adamantyl, charge carrier mobilities

Released

12.09.2018

Publisher

Vysoké učení technické v Brně, Fakulta chemická

Location

Purkyňova 464/118, 612 00 Brno

ISBN

978-80-214-5488-0

Book

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

Edition number

první

Pages from

93

Pages to

93

Pages count

1

Documents

BibTex


@misc{BUT156095,
  author="Alexander {Kovalenko} and Patricie {Heinrichová} and Stanislav {Stříteský} and Martin {Vala} and Martin {Weiter} and Jozef {Krajčovič}",
  title="Implementation of polycyclic cycloalkane systems: a path to highperforming,
soluble, versatile and sustainable organic
semiconducting materials",
  annote="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].",
  address="Vysoké učení technické v Brně, Fakulta chemická",
  booktitle="7th Meeting on Chemistry and Life 2018. Book of abstracts",
  chapter="156095",
  howpublished="print",
  institution="Vysoké učení technické v Brně, Fakulta chemická",
  year="2018",
  month="september",
  pages="93--93",
  publisher="Vysoké učení technické v Brně, Fakulta chemická",
  type="abstract"
}