Syntheses, Structures, and Properties of Phosphorescent Iridium(III) Complexes Containing N-Heterocyclic Carbene Ligands

Ler Chun Shiu, Shin Hung, I-Jy Chang, Kom Bei Shiu

Research output: Contribution to journalArticle

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Abstract

The organic salts 1-(2-pyridylmethyl)-3-alkylbenzimidazolium halide (pm-RbH+X) and 1-(2-pyridylmethyl)-3-alkylimidazolium halide (pm-R′iH+X′) were prepared (where R = 4-, 3-, 2-fluorobenzyl (4f, 3f, and 2f, respectively), 4-, 3-, 2-chlorobenzyl (4c, 3c, and 2c, respectively); 4-methoxybenzyl (4mo); 2,3,4,5,6-pentafluorobenzyl (f5); benzyl (b); and methyl (m)); X = Cl and Br; R′ = benzyl (b) and methyl (m); and X′ = Cl and I. From these salts, heteroleptic Ir(III) complexes containing one N-heterocyclic carbene (NHC) ligand [Ir(κ2-ppy)22-(pm-Rb))]PF6 (R = 4f, 1(PF6); 3f, 2(PF6); 2f, 3(PF6); f5b, 4(PF6); 4c, 5(PF6); 3c, 6(PF6); 2c, 7(PF6); 4mo, 8(PF6); b, 9(PF6); m, 10(PF6)) and [Ir(κ2-ppy)22-(pm-R′i))]PF6 (R = b, 11(PF6); m, 12(PF6)), were synthesized, and the crystal structures of 1(PF6), 2(PF6), 3(PF6), 5(PF6), 6(PF6), 7(PF6), 9(PF6), 10(PF6), and 12(PF6) were determined by X-ray diffraction. The neutral NHC ligands 1-(2-pyridylmethyl)-3-alkylbenzimidazolin-2-ylidene (pm-Rb) and 1-(2-pyridylmethyl)-3-alkylimidazolin-2-ylidene (pm-R′i) of all cations were found to be involved in the intermolecular π−π stacking interactions with the surrounding cations in the solid state, thereby probably influencing the photophysical behavior in the solid state and in solution. The absorption and emission properties of all the complexes show only small variations.

Original languageEnglish
Pages (from-to)843-850
Number of pages8
JournalJournal of the Chinese Chemical Society
Volume64
Issue number7
DOIs
Publication statusPublished - 2017 Jul 1

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Iridium
Cations
Salts
Ligands
Crystal structure
X ray diffraction
carbene

Keywords

  • Carbenes
  • Iridium
  • Luminescence
  • Solid-state structures

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Syntheses, Structures, and Properties of Phosphorescent Iridium(III) Complexes Containing N-Heterocyclic Carbene Ligands. / Shiu, Ler Chun; Hung, Shin; Chang, I-Jy; Shiu, Kom Bei.

In: Journal of the Chinese Chemical Society, Vol. 64, No. 7, 01.07.2017, p. 843-850.

Research output: Contribution to journalArticle

@article{ab92211c8fa5443799576edb1a7ed136,
title = "Syntheses, Structures, and Properties of Phosphorescent Iridium(III) Complexes Containing N-Heterocyclic Carbene Ligands",
abstract = "The organic salts 1-(2-pyridylmethyl)-3-alkylbenzimidazolium halide (pm-RbH+X−) and 1-(2-pyridylmethyl)-3-alkylimidazolium halide (pm-R′iH+X′−) were prepared (where R = 4-, 3-, 2-fluorobenzyl (4f, 3f, and 2f, respectively), 4-, 3-, 2-chlorobenzyl (4c, 3c, and 2c, respectively); 4-methoxybenzyl (4mo); 2,3,4,5,6-pentafluorobenzyl (f5); benzyl (b); and methyl (m)); X = Cl and Br; R′ = benzyl (b) and methyl (m); and X′ = Cl and I. From these salts, heteroleptic Ir(III) complexes containing one N-heterocyclic carbene (NHC) ligand [Ir(κ2-ppy)2(κ2-(pm-Rb))]PF6 (R = 4f, 1(PF6); 3f, 2(PF6); 2f, 3(PF6); f5b, 4(PF6); 4c, 5(PF6); 3c, 6(PF6); 2c, 7(PF6); 4mo, 8(PF6); b, 9(PF6); m, 10(PF6)) and [Ir(κ2-ppy)2(κ2-(pm-R′i))]PF6 (R = b, 11(PF6); m, 12(PF6)), were synthesized, and the crystal structures of 1(PF6), 2(PF6), 3(PF6), 5(PF6), 6(PF6), 7(PF6), 9(PF6), 10(PF6), and 12(PF6) were determined by X-ray diffraction. The neutral NHC ligands 1-(2-pyridylmethyl)-3-alkylbenzimidazolin-2-ylidene (pm-Rb) and 1-(2-pyridylmethyl)-3-alkylimidazolin-2-ylidene (pm-R′i) of all cations were found to be involved in the intermolecular π−π stacking interactions with the surrounding cations in the solid state, thereby probably influencing the photophysical behavior in the solid state and in solution. The absorption and emission properties of all the complexes show only small variations.",
keywords = "Carbenes, Iridium, Luminescence, Solid-state structures",
author = "Shiu, {Ler Chun} and Shin Hung and I-Jy Chang and Shiu, {Kom Bei}",
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TY - JOUR

T1 - Syntheses, Structures, and Properties of Phosphorescent Iridium(III) Complexes Containing N-Heterocyclic Carbene Ligands

AU - Shiu, Ler Chun

AU - Hung, Shin

AU - Chang, I-Jy

AU - Shiu, Kom Bei

PY - 2017/7/1

Y1 - 2017/7/1

N2 - The organic salts 1-(2-pyridylmethyl)-3-alkylbenzimidazolium halide (pm-RbH+X−) and 1-(2-pyridylmethyl)-3-alkylimidazolium halide (pm-R′iH+X′−) were prepared (where R = 4-, 3-, 2-fluorobenzyl (4f, 3f, and 2f, respectively), 4-, 3-, 2-chlorobenzyl (4c, 3c, and 2c, respectively); 4-methoxybenzyl (4mo); 2,3,4,5,6-pentafluorobenzyl (f5); benzyl (b); and methyl (m)); X = Cl and Br; R′ = benzyl (b) and methyl (m); and X′ = Cl and I. From these salts, heteroleptic Ir(III) complexes containing one N-heterocyclic carbene (NHC) ligand [Ir(κ2-ppy)2(κ2-(pm-Rb))]PF6 (R = 4f, 1(PF6); 3f, 2(PF6); 2f, 3(PF6); f5b, 4(PF6); 4c, 5(PF6); 3c, 6(PF6); 2c, 7(PF6); 4mo, 8(PF6); b, 9(PF6); m, 10(PF6)) and [Ir(κ2-ppy)2(κ2-(pm-R′i))]PF6 (R = b, 11(PF6); m, 12(PF6)), were synthesized, and the crystal structures of 1(PF6), 2(PF6), 3(PF6), 5(PF6), 6(PF6), 7(PF6), 9(PF6), 10(PF6), and 12(PF6) were determined by X-ray diffraction. The neutral NHC ligands 1-(2-pyridylmethyl)-3-alkylbenzimidazolin-2-ylidene (pm-Rb) and 1-(2-pyridylmethyl)-3-alkylimidazolin-2-ylidene (pm-R′i) of all cations were found to be involved in the intermolecular π−π stacking interactions with the surrounding cations in the solid state, thereby probably influencing the photophysical behavior in the solid state and in solution. The absorption and emission properties of all the complexes show only small variations.

AB - The organic salts 1-(2-pyridylmethyl)-3-alkylbenzimidazolium halide (pm-RbH+X−) and 1-(2-pyridylmethyl)-3-alkylimidazolium halide (pm-R′iH+X′−) were prepared (where R = 4-, 3-, 2-fluorobenzyl (4f, 3f, and 2f, respectively), 4-, 3-, 2-chlorobenzyl (4c, 3c, and 2c, respectively); 4-methoxybenzyl (4mo); 2,3,4,5,6-pentafluorobenzyl (f5); benzyl (b); and methyl (m)); X = Cl and Br; R′ = benzyl (b) and methyl (m); and X′ = Cl and I. From these salts, heteroleptic Ir(III) complexes containing one N-heterocyclic carbene (NHC) ligand [Ir(κ2-ppy)2(κ2-(pm-Rb))]PF6 (R = 4f, 1(PF6); 3f, 2(PF6); 2f, 3(PF6); f5b, 4(PF6); 4c, 5(PF6); 3c, 6(PF6); 2c, 7(PF6); 4mo, 8(PF6); b, 9(PF6); m, 10(PF6)) and [Ir(κ2-ppy)2(κ2-(pm-R′i))]PF6 (R = b, 11(PF6); m, 12(PF6)), were synthesized, and the crystal structures of 1(PF6), 2(PF6), 3(PF6), 5(PF6), 6(PF6), 7(PF6), 9(PF6), 10(PF6), and 12(PF6) were determined by X-ray diffraction. The neutral NHC ligands 1-(2-pyridylmethyl)-3-alkylbenzimidazolin-2-ylidene (pm-Rb) and 1-(2-pyridylmethyl)-3-alkylimidazolin-2-ylidene (pm-R′i) of all cations were found to be involved in the intermolecular π−π stacking interactions with the surrounding cations in the solid state, thereby probably influencing the photophysical behavior in the solid state and in solution. The absorption and emission properties of all the complexes show only small variations.

KW - Carbenes

KW - Iridium

KW - Luminescence

KW - Solid-state structures

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DO - 10.1002/jccs.201700085

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EP - 850

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JF - Journal of the Chinese Chemical Society

SN - 0009-4536

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