Adamantyl Substitutions as Powerful Tool for Improvement of Thermal and Optical Properties of Organic Solid-State Fluorescent Dyes

presentation, poster

English

The development of new solid-state organic luminescent dyes attracts particular interest due to the wide range of their applications in the field of organic solid-state lasers [1], medical treatment and diagnosis [2], optical fibers [3], and solid state dye-labeled DNA [4]. Para-bis(2-thienyl)phenylene as a dye represent perspective alternative for application in abovementioned fields. Here, we focus on the effects of fluorine atoms attached to the central phenyl unit of the para-bis(2-thienyl)phenylenes and the effect of substitutions on the thiophenes units. Generally, incorporating electron-withdrawing fluorine atoms enables HOMO and LUMO energies tuning as well as molecular organization control because of π-stacked supramolecular organization in the solid state due to strong interaction between electron-poor fluorinated aromatic rings and non-fluorinated electron-rich rings [5]. On the other hand, adamantane units bestow high thermal and chemical stability and self-assembly on the molecules what has a crucial effect for the nanoscaled films production for the applications into the functional devices. Substitutions on the thiophene units with adamantylethyl groups significantly increased melting point from 55 °C to 250 °C and photoluminescence quantum yield up to 50 % [6]. With regards to the possibility of well-targeted chemical modifications for the individual purposes, these molecules are determined for the use in organic electronics.

adamantane, organic electronics, photoluminescence quantum yield

JANČÍK, J.; JANČÍK PROCHÁZKOVÁ, A.; YUMUSAK, C.; SARICIFTCI, N.; KRAJČOVIČ, J.

23. 10. 2019

Nanocon

Brno

1