Synthesis, characterization and DFT calculation of 4-fluorophenyl substituted tris(8-hydroxyquinoline)aluminum(III) complexes

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

New 4-fluorophenyl substituted 8-hydroxyquinoline derivatives, 5-(4-fluorophenyl)quinolin-8-ol and 5,7-bis(4-fluorophenyl)quinolin-8-ol, were synthesized and characterized by spectroscopic methods. The aluminum complexes of 5-(4-fluorophenyl)quinolin-8-ol (AlQF) and of 5,7-bis(4-fluorophenyl) quinolin-8-ol (AlQF2) exhibit strong fluorescence emission centered at 525 nm and 530 nm respectively. The quantum yield of both complexes were enhanced compared to the parent tris(8-hydroxyquinolinato)aluminum(III) complex. Electronic structures and photophysical properties of the new complexes were investigated theoretically by ab initio and density functional theory (DFT) and time dependent DFT (TD-DFT). Geometries of the ground state (S0) and the first excited state (S1) of the new complexes were optimized at the B3LYP/6-31G(d) functional and configuration interaction singles (CIS) method respectively. The aryl substituents were found to contribute significantly to the frontier molecular orbitals (FMOs). We have observed that in both cases the lowest occupied molecular orbital (LUMO) energy decreases while the energy of the highest occupied molecular orbital is slightly increased. The most significant increase was observed for AlQF2.

Original languageEnglish
Pages (from-to)66-72
Number of pages7
JournalSpectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Volume118
DOIs
Publication statusPublished - 2014

Fingerprint

quinoline
Molecular orbitals
Aluminum
Density functional theory
density functional theory
aluminum
Oxyquinoline
molecular orbitals
synthesis
Fluorescence
Quantum yield
Excited states
Ground state
Electronic structure
configuration interaction
Derivatives
Geometry
electronic structure
fluorescence
ground state

Keywords

  • 8-Hydroxyquinoline
  • Aluminum(III) complexes
  • Fluorescence
  • OLEDs
  • TD-DFT

ASJC Scopus subject areas

  • Instrumentation
  • Atomic and Molecular Physics, and Optics
  • Analytical Chemistry
  • Spectroscopy
  • Medicine(all)

Cite this

@article{4c9d93b0240849818673bac6cb50ae10,
title = "Synthesis, characterization and DFT calculation of 4-fluorophenyl substituted tris(8-hydroxyquinoline)aluminum(III) complexes",
abstract = "New 4-fluorophenyl substituted 8-hydroxyquinoline derivatives, 5-(4-fluorophenyl)quinolin-8-ol and 5,7-bis(4-fluorophenyl)quinolin-8-ol, were synthesized and characterized by spectroscopic methods. The aluminum complexes of 5-(4-fluorophenyl)quinolin-8-ol (AlQF) and of 5,7-bis(4-fluorophenyl) quinolin-8-ol (AlQF2) exhibit strong fluorescence emission centered at 525 nm and 530 nm respectively. The quantum yield of both complexes were enhanced compared to the parent tris(8-hydroxyquinolinato)aluminum(III) complex. Electronic structures and photophysical properties of the new complexes were investigated theoretically by ab initio and density functional theory (DFT) and time dependent DFT (TD-DFT). Geometries of the ground state (S0) and the first excited state (S1) of the new complexes were optimized at the B3LYP/6-31G(d) functional and configuration interaction singles (CIS) method respectively. The aryl substituents were found to contribute significantly to the frontier molecular orbitals (FMOs). We have observed that in both cases the lowest occupied molecular orbital (LUMO) energy decreases while the energy of the highest occupied molecular orbital is slightly increased. The most significant increase was observed for AlQF2.",
keywords = "8-Hydroxyquinoline, Aluminum(III) complexes, Fluorescence, OLEDs, TD-DFT",
author = "Suliman, {Fakhreldin O.} and Isehaq Al-Nafai and Al-Busafi, {Saleh N.}",
year = "2014",
doi = "10.1016/j.saa.2013.08.055",
language = "English",
volume = "118",
pages = "66--72",
journal = "Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy",
issn = "1386-1425",
publisher = "Elsevier",

}

TY - JOUR

T1 - Synthesis, characterization and DFT calculation of 4-fluorophenyl substituted tris(8-hydroxyquinoline)aluminum(III) complexes

AU - Suliman, Fakhreldin O.

AU - Al-Nafai, Isehaq

AU - Al-Busafi, Saleh N.

PY - 2014

Y1 - 2014

N2 - New 4-fluorophenyl substituted 8-hydroxyquinoline derivatives, 5-(4-fluorophenyl)quinolin-8-ol and 5,7-bis(4-fluorophenyl)quinolin-8-ol, were synthesized and characterized by spectroscopic methods. The aluminum complexes of 5-(4-fluorophenyl)quinolin-8-ol (AlQF) and of 5,7-bis(4-fluorophenyl) quinolin-8-ol (AlQF2) exhibit strong fluorescence emission centered at 525 nm and 530 nm respectively. The quantum yield of both complexes were enhanced compared to the parent tris(8-hydroxyquinolinato)aluminum(III) complex. Electronic structures and photophysical properties of the new complexes were investigated theoretically by ab initio and density functional theory (DFT) and time dependent DFT (TD-DFT). Geometries of the ground state (S0) and the first excited state (S1) of the new complexes were optimized at the B3LYP/6-31G(d) functional and configuration interaction singles (CIS) method respectively. The aryl substituents were found to contribute significantly to the frontier molecular orbitals (FMOs). We have observed that in both cases the lowest occupied molecular orbital (LUMO) energy decreases while the energy of the highest occupied molecular orbital is slightly increased. The most significant increase was observed for AlQF2.

AB - New 4-fluorophenyl substituted 8-hydroxyquinoline derivatives, 5-(4-fluorophenyl)quinolin-8-ol and 5,7-bis(4-fluorophenyl)quinolin-8-ol, were synthesized and characterized by spectroscopic methods. The aluminum complexes of 5-(4-fluorophenyl)quinolin-8-ol (AlQF) and of 5,7-bis(4-fluorophenyl) quinolin-8-ol (AlQF2) exhibit strong fluorescence emission centered at 525 nm and 530 nm respectively. The quantum yield of both complexes were enhanced compared to the parent tris(8-hydroxyquinolinato)aluminum(III) complex. Electronic structures and photophysical properties of the new complexes were investigated theoretically by ab initio and density functional theory (DFT) and time dependent DFT (TD-DFT). Geometries of the ground state (S0) and the first excited state (S1) of the new complexes were optimized at the B3LYP/6-31G(d) functional and configuration interaction singles (CIS) method respectively. The aryl substituents were found to contribute significantly to the frontier molecular orbitals (FMOs). We have observed that in both cases the lowest occupied molecular orbital (LUMO) energy decreases while the energy of the highest occupied molecular orbital is slightly increased. The most significant increase was observed for AlQF2.

KW - 8-Hydroxyquinoline

KW - Aluminum(III) complexes

KW - Fluorescence

KW - OLEDs

KW - TD-DFT

UR - http://www.scopus.com/inward/record.url?scp=84883732835&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84883732835&partnerID=8YFLogxK

U2 - 10.1016/j.saa.2013.08.055

DO - 10.1016/j.saa.2013.08.055

M3 - Article

VL - 118

SP - 66

EP - 72

JO - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

JF - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

SN - 1386-1425

ER -