Thiazolo[5,4-]thiazoles with a spirobifluorene moiety as novel D-π-A type organic hosts: design, synthesis, structure-property relationship and applications in electroluminescent devices

A series of thiazolo[5,4- d ]thiazoles with bipolar character has been designed and synthesized. Compounds 4a-d and 5a,b consist of a central thiazolo[5,4- d ]thiazole as the electron acceptor (A) and a terminal 9,9′-spirobifluorene fragment as the electron-donor (D). Both key structural features ar...

Full description

Saved in:
Bibliographic Details
Published in:New journal of chemistry 2023-06, Vol.47 (23), p.11165-11175
Main Authors: Eckstein-Andicsová, Anita, Tokárová, Zita, Kozma, Erika, Balogh, Róbert, Vykydalová, Anna, Mróz, Wojciech, Tokár, Kamil
Format: Article
Language:English
Subjects:
Electroluminescence
Energy gap
Molecular orbitals
Optoelectronic devices
Thermal stability
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A series of thiazolo[5,4- d ]thiazoles with bipolar character has been designed and synthesized. Compounds 4a-d and 5a,b consist of a central thiazolo[5,4- d ]thiazole as the electron acceptor (A) and a terminal 9,9′-spirobifluorene fragment as the electron-donor (D). Both key structural features are connected through the thiophene π-linker. The structure of all the compounds is fully π-conjugated providing proximity of the frontier molecular orbitals (FMO). Accordingly, thiazolo[5,4- d ]thiazole-based compounds 4a-d and 5a,b exhibit excellent electronic structures with energy gaps falling in the range of 2.5-3.0 eV. Appropriate thermal stability and valuable photophysical properties make these molecules valuable for applications in optoelectronic materials. Hence, electroluminescent devices with 4b and 5b as host materials showed yellowish-green and yellow-green emissions, which is quite unique for organic-small molecules demonstrating their potential in the development of novel, low-weight and fully organic dopants for electroluminescent (EL) devices. Novel D-π-A type organic small-molecules with thiazolo[5,4- d ]thiazole and spirobifluorene units. Optoelectronical properties suggests their applications in materials. Electroluminescent devices containing the novel TzTz-based derivatives 4b , 5b show affinitive emission.
ISSN:1144-0546
1369-9261
DOI:10.1039/d3nj01633a