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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
Type
abstract
Language
English
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].
Keywords
diketopyrrolopyrroles, ethyl-adamantyl, charge carrier mobilities
Authors
KOVALENKO, A.;YUMASAK, C.; HEINRICHOVÁ, P.; STŘÍTESKÝ, S.; VALA, M.; WEITER, M.; SARICIFCI N.S.; KRAJČOVIČ, J.
Released
12. 9. 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
Pages count
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" }