Synthesis and photophysical characteristics of 2,7-fluorenevinylene-based trimers and their electroluminescence

John A. Mikroyannidis, Larysa Fenenko, Chihaya Adachi

Research output: Contribution to journalArticle

52 Citations (Scopus)

Abstract

Three new 2,7-fluorenevinylene-based trimers were synthesized and characterized. The synthesis was carried out by the Heck coupling reaction of 9,9-dihexyl-2,7-divinylfluorene with 2-(4-bromophenyl)-5-phenyl-1,3,4- oxadiazole, N,N-diphenyl-4-bromoaniline, or 3-bromopyrene to afford the trimers OXD, TPA, and PYR, respectively. All the trimers were readily soluble in common organic solvents such as tetrahydrofuran, dichloromethane, chloroform, and toluene. Their glass transition temperatures ranged from 33 to 60°C. The UV-vis spectra showed an absorption maximum at λa,max = 379-417 nm with optical band gap of Eg = 2.47-2.66 eV. In solution, they emitted strong blue-green photoluminescence (PL) with PL maximum at λf,max = 455-565 nm and fluorescence quantum yield of Φf = 0.65-0.74. On the other hand, in their spin-coated films, the PL efficiencies significantly decreased due to the presence of concentration quenching. All samples showed nanosecond transient lifetime containing two components, suggesting excimer formation. The organic light-emitting diodes (OLEDs) with OXD and TPA showed green emission with electroluminescence (EL) quantum efficiencies of ηEL ∼ 10-2%, while very weak EL efficiency of ηEL ∼ 10-5% was observed with PYR. The highest occupied molecular orbital (HOMO) levels of the films were found to be 5.05-5.75 eV.

Original languageEnglish
Pages (from-to)20317-20326
Number of pages10
JournalJournal of Physical Chemistry B
Volume110
Issue number41
DOIs
Publication statusPublished - Oct 19 2006

Fingerprint

Transition Temperature
Methylene Chloride
Electroluminescence
Toluene
Chloroform
trimers
electroluminescence
Glass
Fluorescence
Light
Photoluminescence
synthesis
photoluminescence
Optical band gaps
Dichloromethane
Organic light emitting diodes (OLED)
Quantum yield
Molecular orbitals
excimers
Chlorine compounds

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Surfaces, Coatings and Films
  • Materials Chemistry

Cite this

Synthesis and photophysical characteristics of 2,7-fluorenevinylene-based trimers and their electroluminescence. / Mikroyannidis, John A.; Fenenko, Larysa; Adachi, Chihaya.

In: Journal of Physical Chemistry B, Vol. 110, No. 41, 19.10.2006, p. 20317-20326.

Research output: Contribution to journalArticle

@article{49cc2aaafbce4ebcaebcfb7d38747860,
title = "Synthesis and photophysical characteristics of 2,7-fluorenevinylene-based trimers and their electroluminescence",
abstract = "Three new 2,7-fluorenevinylene-based trimers were synthesized and characterized. The synthesis was carried out by the Heck coupling reaction of 9,9-dihexyl-2,7-divinylfluorene with 2-(4-bromophenyl)-5-phenyl-1,3,4- oxadiazole, N,N-diphenyl-4-bromoaniline, or 3-bromopyrene to afford the trimers OXD, TPA, and PYR, respectively. All the trimers were readily soluble in common organic solvents such as tetrahydrofuran, dichloromethane, chloroform, and toluene. Their glass transition temperatures ranged from 33 to 60°C. The UV-vis spectra showed an absorption maximum at λa,max = 379-417 nm with optical band gap of Eg = 2.47-2.66 eV. In solution, they emitted strong blue-green photoluminescence (PL) with PL maximum at λf,max = 455-565 nm and fluorescence quantum yield of Φf = 0.65-0.74. On the other hand, in their spin-coated films, the PL efficiencies significantly decreased due to the presence of concentration quenching. All samples showed nanosecond transient lifetime containing two components, suggesting excimer formation. The organic light-emitting diodes (OLEDs) with OXD and TPA showed green emission with electroluminescence (EL) quantum efficiencies of ηEL ∼ 10-2{\%}, while very weak EL efficiency of ηEL ∼ 10-5{\%} was observed with PYR. The highest occupied molecular orbital (HOMO) levels of the films were found to be 5.05-5.75 eV.",
author = "Mikroyannidis, {John A.} and Larysa Fenenko and Chihaya Adachi",
year = "2006",
month = "10",
day = "19",
doi = "10.1021/jp0631477",
language = "English",
volume = "110",
pages = "20317--20326",
journal = "Journal of Physical Chemistry B",
issn = "1520-6106",
number = "41",

}

TY - JOUR

T1 - Synthesis and photophysical characteristics of 2,7-fluorenevinylene-based trimers and their electroluminescence

AU - Mikroyannidis, John A.

AU - Fenenko, Larysa

AU - Adachi, Chihaya

PY - 2006/10/19

Y1 - 2006/10/19

N2 - Three new 2,7-fluorenevinylene-based trimers were synthesized and characterized. The synthesis was carried out by the Heck coupling reaction of 9,9-dihexyl-2,7-divinylfluorene with 2-(4-bromophenyl)-5-phenyl-1,3,4- oxadiazole, N,N-diphenyl-4-bromoaniline, or 3-bromopyrene to afford the trimers OXD, TPA, and PYR, respectively. All the trimers were readily soluble in common organic solvents such as tetrahydrofuran, dichloromethane, chloroform, and toluene. Their glass transition temperatures ranged from 33 to 60°C. The UV-vis spectra showed an absorption maximum at λa,max = 379-417 nm with optical band gap of Eg = 2.47-2.66 eV. In solution, they emitted strong blue-green photoluminescence (PL) with PL maximum at λf,max = 455-565 nm and fluorescence quantum yield of Φf = 0.65-0.74. On the other hand, in their spin-coated films, the PL efficiencies significantly decreased due to the presence of concentration quenching. All samples showed nanosecond transient lifetime containing two components, suggesting excimer formation. The organic light-emitting diodes (OLEDs) with OXD and TPA showed green emission with electroluminescence (EL) quantum efficiencies of ηEL ∼ 10-2%, while very weak EL efficiency of ηEL ∼ 10-5% was observed with PYR. The highest occupied molecular orbital (HOMO) levels of the films were found to be 5.05-5.75 eV.

AB - Three new 2,7-fluorenevinylene-based trimers were synthesized and characterized. The synthesis was carried out by the Heck coupling reaction of 9,9-dihexyl-2,7-divinylfluorene with 2-(4-bromophenyl)-5-phenyl-1,3,4- oxadiazole, N,N-diphenyl-4-bromoaniline, or 3-bromopyrene to afford the trimers OXD, TPA, and PYR, respectively. All the trimers were readily soluble in common organic solvents such as tetrahydrofuran, dichloromethane, chloroform, and toluene. Their glass transition temperatures ranged from 33 to 60°C. The UV-vis spectra showed an absorption maximum at λa,max = 379-417 nm with optical band gap of Eg = 2.47-2.66 eV. In solution, they emitted strong blue-green photoluminescence (PL) with PL maximum at λf,max = 455-565 nm and fluorescence quantum yield of Φf = 0.65-0.74. On the other hand, in their spin-coated films, the PL efficiencies significantly decreased due to the presence of concentration quenching. All samples showed nanosecond transient lifetime containing two components, suggesting excimer formation. The organic light-emitting diodes (OLEDs) with OXD and TPA showed green emission with electroluminescence (EL) quantum efficiencies of ηEL ∼ 10-2%, while very weak EL efficiency of ηEL ∼ 10-5% was observed with PYR. The highest occupied molecular orbital (HOMO) levels of the films were found to be 5.05-5.75 eV.

UR - http://www.scopus.com/inward/record.url?scp=33751272763&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33751272763&partnerID=8YFLogxK

U2 - 10.1021/jp0631477

DO - 10.1021/jp0631477

M3 - Article

C2 - 17034213

AN - SCOPUS:33751272763

VL - 110

SP - 20317

EP - 20326

JO - Journal of Physical Chemistry B

JF - Journal of Physical Chemistry B

SN - 1520-6106

IS - 41

ER -