Publication detail

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

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

Original Title

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

English Title

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

Language

en

Original Abstract

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.

English abstract

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.

Keywords

adamantane, organic electronics, photoluminescence quantum yield

Released

23.10.2019

Publisher

Nanocon

Location

Brno

Pages count

1

Documents

BibTex


@misc{BUT160950,
  author="Ján {Jančík} and Anna {Jančík Procházková} and Cigdem {Yumusak} and Niyazi Serdar {Sariciftci} and Jozef {Krajčovič}",
  title="Adamantyl Substitutions as Powerful Tool for Improvement of Thermal and Optical Properties of Organic Solid-State Fluorescent Dyes",
  annote="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.
",
  address="Nanocon",
  chapter="160950",
  howpublished="online",
  institution="Nanocon",
  year="2019",
  month="october",
  publisher="Nanocon"
}