Photoelectric properties of novel amide-functionalized Ir(III) complexes

Wei Shen, Wen Wen Tian, Zheng Jian Qi, Yue Ming Sun

Research output: Contribution to journalArticleResearchpeer-review

Abstract

A series of luminescent cyclometalated Ir(III) complexes functionalized with amide derivatives were prepared and compared with [Ir(ppy)2phen-NH2]Cl. The complexes were [Ir(ppy)2phen-Br]Cl, [Ir(ppy)2phen-COOH]Cl, and [Ir(ppy)2phen-Si]Cl, where ppy is 2-phenylpyridine, phen-NH2 is 5-amino-[1,10]-phenanthroline, phen-Br is 2-bromo-2-methyl-N-(1,10-phenanthrolin-5-yl)propanamide, phen-COOH is 4-[(1,10-phenanthrolin-5-yl)amino]-4-oxobut-2-enoic acid, and phen-Si is 5-[N,N-bis-3-(triethoxysilyl) propyl]ureyl-1,10-phenanthroline. They were characterized using nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), ultraviolet-visible (UV-Vis) absorption spectroscopy, photoluminescence (PL) spectroscopy, and cyclic voltammetry (CV). The three novel complexes have intense absorptions in the blue-purple region. The complexes show bright yellow to orange PL emissions under UV irradiation, and the quantum yields (Φ) of these complexes are higher than 12%. The excited-state lifetimes of the novel complexes are 9.18–12.00 μs, much longer than that of [Ir(ppy)2phen-NH2]Cl (5.78 μs). With both the highest quantum yield (32%) and longest lifetime (12.00 μs), [Ir(ppy)2phen-Br]Cl also shows the best oxygen-sensing properties and the largest I0/I factor, 10.91 (I0: the PL intensity of the complex in the absence of O2, I: the PL intensity of the complex under pure oxygen). These results suggest that [Ir(ppy)2phen-Br]Cl may be a promising candidate for use in oxygen sensors based on covalent grafting. Time-dependent density functional theory (TD-DFT) calculations were used to supplement the photoelectric property studies. Theoretical calculations indicate that all the mononuclear complexes have approximately octahedral structures with Ir(III) as the coordination center. The computational results agree well with the experimental data.

Original languageEnglish
Pages (from-to)2174-2182
Number of pages9
JournalWuli Huaxue Xuebao/ Acta Physico - Chimica Sinica
Volume31
Issue number11
DOIs
Publication statusPublished - 13 Nov 2015
Externally publishedYes

Keywords

  • Ir(III) complex
  • Luminescence sensor
  • Oxygen quenching
  • Phenanthroline
  • Photoelectric property

Cite this

Shen, Wei ; Tian, Wen Wen ; Qi, Zheng Jian ; Sun, Yue Ming. / Photoelectric properties of novel amide-functionalized Ir(III) complexes. In: Wuli Huaxue Xuebao/ Acta Physico - Chimica Sinica. 2015 ; Vol. 31, No. 11. pp. 2174-2182.
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title = "Photoelectric properties of novel amide-functionalized Ir(III) complexes",
abstract = "A series of luminescent cyclometalated Ir(III) complexes functionalized with amide derivatives were prepared and compared with [Ir(ppy)2phen-NH2]Cl. The complexes were [Ir(ppy)2phen-Br]Cl, [Ir(ppy)2phen-COOH]Cl, and [Ir(ppy)2phen-Si]Cl, where ppy is 2-phenylpyridine, phen-NH2 is 5-amino-[1,10]-phenanthroline, phen-Br is 2-bromo-2-methyl-N-(1,10-phenanthrolin-5-yl)propanamide, phen-COOH is 4-[(1,10-phenanthrolin-5-yl)amino]-4-oxobut-2-enoic acid, and phen-Si is 5-[N,N-bis-3-(triethoxysilyl) propyl]ureyl-1,10-phenanthroline. They were characterized using nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), ultraviolet-visible (UV-Vis) absorption spectroscopy, photoluminescence (PL) spectroscopy, and cyclic voltammetry (CV). The three novel complexes have intense absorptions in the blue-purple region. The complexes show bright yellow to orange PL emissions under UV irradiation, and the quantum yields (Φ) of these complexes are higher than 12{\%}. The excited-state lifetimes of the novel complexes are 9.18–12.00 μs, much longer than that of [Ir(ppy)2phen-NH2]Cl (5.78 μs). With both the highest quantum yield (32{\%}) and longest lifetime (12.00 μs), [Ir(ppy)2phen-Br]Cl also shows the best oxygen-sensing properties and the largest I0/I factor, 10.91 (I0: the PL intensity of the complex in the absence of O2, I: the PL intensity of the complex under pure oxygen). These results suggest that [Ir(ppy)2phen-Br]Cl may be a promising candidate for use in oxygen sensors based on covalent grafting. Time-dependent density functional theory (TD-DFT) calculations were used to supplement the photoelectric property studies. Theoretical calculations indicate that all the mononuclear complexes have approximately octahedral structures with Ir(III) as the coordination center. The computational results agree well with the experimental data.",
keywords = "Ir(III) complex, Luminescence sensor, Oxygen quenching, Phenanthroline, Photoelectric property",
author = "Wei Shen and Tian, {Wen Wen} and Qi, {Zheng Jian} and Sun, {Yue Ming}",
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Photoelectric properties of novel amide-functionalized Ir(III) complexes. / Shen, Wei; Tian, Wen Wen; Qi, Zheng Jian; Sun, Yue Ming.

In: Wuli Huaxue Xuebao/ Acta Physico - Chimica Sinica, Vol. 31, No. 11, 13.11.2015, p. 2174-2182.

Research output: Contribution to journalArticleResearchpeer-review

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T1 - Photoelectric properties of novel amide-functionalized Ir(III) complexes

AU - Shen, Wei

AU - Tian, Wen Wen

AU - Qi, Zheng Jian

AU - Sun, Yue Ming

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N2 - A series of luminescent cyclometalated Ir(III) complexes functionalized with amide derivatives were prepared and compared with [Ir(ppy)2phen-NH2]Cl. The complexes were [Ir(ppy)2phen-Br]Cl, [Ir(ppy)2phen-COOH]Cl, and [Ir(ppy)2phen-Si]Cl, where ppy is 2-phenylpyridine, phen-NH2 is 5-amino-[1,10]-phenanthroline, phen-Br is 2-bromo-2-methyl-N-(1,10-phenanthrolin-5-yl)propanamide, phen-COOH is 4-[(1,10-phenanthrolin-5-yl)amino]-4-oxobut-2-enoic acid, and phen-Si is 5-[N,N-bis-3-(triethoxysilyl) propyl]ureyl-1,10-phenanthroline. They were characterized using nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), ultraviolet-visible (UV-Vis) absorption spectroscopy, photoluminescence (PL) spectroscopy, and cyclic voltammetry (CV). The three novel complexes have intense absorptions in the blue-purple region. The complexes show bright yellow to orange PL emissions under UV irradiation, and the quantum yields (Φ) of these complexes are higher than 12%. The excited-state lifetimes of the novel complexes are 9.18–12.00 μs, much longer than that of [Ir(ppy)2phen-NH2]Cl (5.78 μs). With both the highest quantum yield (32%) and longest lifetime (12.00 μs), [Ir(ppy)2phen-Br]Cl also shows the best oxygen-sensing properties and the largest I0/I factor, 10.91 (I0: the PL intensity of the complex in the absence of O2, I: the PL intensity of the complex under pure oxygen). These results suggest that [Ir(ppy)2phen-Br]Cl may be a promising candidate for use in oxygen sensors based on covalent grafting. Time-dependent density functional theory (TD-DFT) calculations were used to supplement the photoelectric property studies. Theoretical calculations indicate that all the mononuclear complexes have approximately octahedral structures with Ir(III) as the coordination center. The computational results agree well with the experimental data.

AB - A series of luminescent cyclometalated Ir(III) complexes functionalized with amide derivatives were prepared and compared with [Ir(ppy)2phen-NH2]Cl. The complexes were [Ir(ppy)2phen-Br]Cl, [Ir(ppy)2phen-COOH]Cl, and [Ir(ppy)2phen-Si]Cl, where ppy is 2-phenylpyridine, phen-NH2 is 5-amino-[1,10]-phenanthroline, phen-Br is 2-bromo-2-methyl-N-(1,10-phenanthrolin-5-yl)propanamide, phen-COOH is 4-[(1,10-phenanthrolin-5-yl)amino]-4-oxobut-2-enoic acid, and phen-Si is 5-[N,N-bis-3-(triethoxysilyl) propyl]ureyl-1,10-phenanthroline. They were characterized using nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), ultraviolet-visible (UV-Vis) absorption spectroscopy, photoluminescence (PL) spectroscopy, and cyclic voltammetry (CV). The three novel complexes have intense absorptions in the blue-purple region. The complexes show bright yellow to orange PL emissions under UV irradiation, and the quantum yields (Φ) of these complexes are higher than 12%. The excited-state lifetimes of the novel complexes are 9.18–12.00 μs, much longer than that of [Ir(ppy)2phen-NH2]Cl (5.78 μs). With both the highest quantum yield (32%) and longest lifetime (12.00 μs), [Ir(ppy)2phen-Br]Cl also shows the best oxygen-sensing properties and the largest I0/I factor, 10.91 (I0: the PL intensity of the complex in the absence of O2, I: the PL intensity of the complex under pure oxygen). These results suggest that [Ir(ppy)2phen-Br]Cl may be a promising candidate for use in oxygen sensors based on covalent grafting. Time-dependent density functional theory (TD-DFT) calculations were used to supplement the photoelectric property studies. Theoretical calculations indicate that all the mononuclear complexes have approximately octahedral structures with Ir(III) as the coordination center. The computational results agree well with the experimental data.

KW - Ir(III) complex

KW - Luminescence sensor

KW - Oxygen quenching

KW - Phenanthroline

KW - Photoelectric property

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