Publication detail

Effect of adamantane substitutions on para-bis(2-thienyl)phenylene solid-state organic luminescent dyes

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

Original Title

Effect of adamantane substitutions on para-bis(2-thienyl)phenylene solid-state organic luminescent dyes

English Title

Effect of adamantane substitutions on para-bis(2-thienyl)phenylene solid-state organic luminescent dyes

Language

en

Original Abstract

IDTechEx Research finds that the total market for printed, flexible and organic electronics will grow from $41.2 Billion in 2020 to $74 billion in 2030. The majority of that is OLEDs, printed biosensors, printed conductive layers. On the other hand, stretchable electronics, logic and memory, flexible batteries, organic solid-state lasers, materials for medical treatment and diagnosis, optical fibers, solid state dye-labelling for DNA and capacitive sensors are much smaller segments but with strong growth potential. The development of new materials for abovementioned applications attracts interest due to the wide range of their applications. Para-bis(2-thienyl)phenylene as a dye represent perspective alternative for application in abovementioned fields. Here, we focus on the effects of various substitutions on the phenyl and thiophenes units. Incorporation of electron-withdrawing fluorine atoms results in HOMO and LUMO energies tuning and in molecular organization. On the other hand, solubilizing groups on thiophene units have impact on solubility, thermal and chemical stability and self-assembly what has a crucial effect for the device’s fabrication and industrial applications. For example, 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 %. 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

IDTechEx Research finds that the total market for printed, flexible and organic electronics will grow from $41.2 Billion in 2020 to $74 billion in 2030. The majority of that is OLEDs, printed biosensors, printed conductive layers. On the other hand, stretchable electronics, logic and memory, flexible batteries, organic solid-state lasers, materials for medical treatment and diagnosis, optical fibers, solid state dye-labelling for DNA and capacitive sensors are much smaller segments but with strong growth potential. The development of new materials for abovementioned applications attracts interest due to the wide range of their applications. Para-bis(2-thienyl)phenylene as a dye represent perspective alternative for application in abovementioned fields. Here, we focus on the effects of various substitutions on the phenyl and thiophenes units. Incorporation of electron-withdrawing fluorine atoms results in HOMO and LUMO energies tuning and in molecular organization. On the other hand, solubilizing groups on thiophene units have impact on solubility, thermal and chemical stability and self-assembly what has a crucial effect for the device’s fabrication and industrial applications. For example, 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 %. 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

21.11.2019

Publisher

Vysoké učení technické v Brně, Fakulta chemická, Purkyňova 464/118, 61200 Brno

Location

Brno

Pages from

77

Pages to

77

Pages count

90

Documents

BibTex


@misc{BUT161523,
  author="Ján {Jančík} and Anna {Jančík Procházková} and Cigdem {Yumusak} and Niyazi Serdar {Sariciftci} and Jozef {Krajčovič}",
  title="Effect of adamantane substitutions on
 para-bis(2-thienyl)phenylene solid-state organic luminescent dyes",
  annote="IDTechEx Research finds that the total market for printed, flexible and organic electronics will grow from $41.2 Billion in 2020 to $74 billion in 2030. The majority of that is OLEDs, printed biosensors, printed conductive layers. On the other hand, stretchable electronics, logic and memory, flexible batteries, organic solid-state lasers, materials for medical treatment and diagnosis, optical fibers, solid state dye-labelling for DNA and capacitive sensors are much smaller segments but with strong growth potential. The development of new materials for abovementioned applications attracts interest due to the wide range of their applications. Para-bis(2-thienyl)phenylene as a dye represent perspective alternative for application in abovementioned fields. Here, we focus on the effects of various substitutions on the phenyl and thiophenes units. Incorporation of electron-withdrawing fluorine atoms results in HOMO and LUMO energies tuning and in molecular organization. On the other hand, solubilizing groups on thiophene units have impact on solubility, thermal and chemical stability and self-assembly what has a crucial effect for the device’s fabrication and industrial applications. For example, 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 %.
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="Vysoké učení technické v Brně, Fakulta chemická, Purkyňova 464/118, 61200 Brno",
  chapter="161523",
  howpublished="print",
  institution="Vysoké učení technické v Brně, Fakulta chemická, Purkyňova 464/118, 61200 Brno",
  year="2019",
  month="november",
  pages="77--77",
  publisher="Vysoké učení technické v Brně, Fakulta chemická, Purkyňova 464/118, 61200 Brno"
}