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

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

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].

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].

diketopyrrolopyrroles, ethyl-adamantyl, charge carrier mobilities

diketopyrrolopyrroles, ethyl-adamantyl, charge carrier mobilities

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

12.09.2018

Vysoké učení technické v Brně, Fakulta chemická

Purkyňova 464/118, 612 00 Brno

978-80-214-5488-0

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

93

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