Side chain engineering: the role of bulky substituents towards to original properties of organic optoelectronic materials

abstrakt

angličtina

Soluble organic optolectronic materials have a particular application potential for easily processed lowcost organic electronics devices. Solubility of organic π-conjugated small molecule derivatives, such as diketopyrrolopyrroles (DPPs), indigos, epindolidiones, squaraines and many others is usually attained by a side-chain alkyl substitution. Nowadays many organic semiconductors have been developed to improve the device performance, where most of the efforts focus on the design and synthesis of new π-conjugated backbones. The alkyl side chain substitution of single molecules and polymer chains cause several important changes that are closely related to properties and directly to further use of π-conjugated systems. Adamantane and its derivatives are atypical fragments for side-chain alkyl substitution. However, adamantane is the simplest diamondoid, possesses exceptional physical characteristics and is the most stable saturated hydrocarbon isomer of such a small molecular weight. Above mentioned approach offers the synthesis of 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 π-conjugated dyes in the solid state. Above mentioned side chain can improve solid-state fluorescence quantum yields of the materials and significantly increase the melting points. Considering electrical properties, as an example, a soluble DPP derivative with ethyl adamantyl side-groups showed abmipolar behavior with both hole and electron mobilities higher than the insoluble analogue. Easily processable and convenient for upscaling and industrial processing, two novel thermodynamically stable regioregular poly-3- adamantylmethylthiophene and poly-3-adamantylethylthiophene polymers were investigated. The prepared adamantane polythiophenes possess excellent thermal and chemical stability, which are important properties to produce stable and long-life devices.

diketopyrrolopyrrole; adamantane; side-chain engineering; optoelectronics

Krajčovič, J.; Cigánek, M.; Blasi, D.; Yumusak, C.; Sariciftci, N. S.

2. 10. 2023

Universitá degli studi di Bari Aldo Moro

Bari, Itálie

978-88-94952-41-4

16th European Conference on Molecular Electronics - ABSTRACT BOOK

56

56

1

https://www.ecme2023.eu/book-of-abstract/