Synthesis, light-emitting, and two-photon absorption properties of platinum-containing poly(arylene-ethynylene)s linked by 1,3,4-oxadiazole units

Thomas Goudreault; Ze He; Yanhe Guo; Cheuk Lam Ho; Hongmei Zhan; Qiwei Wang; Keith Yat Fung Ho; Ka Leung Wong; Daniel Fortin; Bing Yao; Zhiyuan Xie; Lixiang Wang; Wai Ming Kwok; Pierre D. Harvey; Wai Yeung Wong

doi:10.1021/ma1009319

Synthesis, light-emitting, and two-photon absorption properties of platinum-containing poly(arylene-ethynylene)s linked by 1,3,4-oxadiazole units

Thomas Goudreault, Ze He, Yanhe Guo, Cheuk Lam Ho, Hongmei Zhan, Qiwei Wang, Keith Yat Fung Ho, Ka Leung Wong, Daniel Fortin, Bing Yao, Zhiyuan Xie, Lixiang Wang, Wai Ming Kwok, Pierre D. Harvey, Wai Yeung Wong

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

62 Citations (Scopus)

Abstract

A series of soluble and thermally stable group 10 platinum(II) polyyne polymers of the type [-C≡C-Pt(PBu₃)₂-C≡C-Ar- Ox-Ar-]_n (where Ox = 1,3,4-oxadiazole; Ar = p-C₆H ₄ or 2,7-dihexyl-9,9-fluorene) and [-C≡C-Pt(PBu ₃)₂-C≡C-Ar-Ox-Ar-Ox-Ar-]_n (where Ar = 2,7-dihexyl-9,9-fluorene) along with their corresponding dinuclear model compounds [Ph-Pt(PEt₃)₂-C≡C-Ar-]₂-Ox- (where Ar = p-C₆H₄ or 2,7-dihexyl-9,9-fluorene) and [Ph-Pt(PEt₃)₂-C≡C-Ar-Ox-]₂-Ar- (where Ar = 2,7-dihexyl-9,9-fluorene) were prepared and characterized. The regiochemical structure of the polymers has been ascertained by single-crystal X-ray analysis on the model compound [Ph-Pt(PEt₃)₂-C≡C-p-C ₆H₄-]₂-Ox-. The photophysical properties (absorption, excitation, emission, and nanosecond transient absorption spectra) of these metalated compounds in 2MeTHF at 298 and 77 K are reported. These findings are correlated by density functional theory (DFT) calculations. Geometry optimizations predict totally planar molecules for these metalated complexes and polymers, allowing better π-conjugation across the main chain. The ligands are strongly fluorescent but become also phosphorescent when the Pt atom is introduced in the backbone of the conjugated organometallic complexes and polymers. These emissions are assigned to ππ* transitions in all cases involving the Pt d_xy orbitals. These Pt compounds exhibit two-photon absorption (2PA), and their 2PA cross sections (σ₂) have been determined. The potential of exploiting such metallopolymers for the design of electrophosphorescent polymer light-emitting devices (PLEDs) and their use as single-dopant for white PLEDs have also been discussed.

Original language	English
Pages (from-to)	7936-7949
Number of pages	14
Journal	Macromolecules
Volume	43
Issue number	19
DOIs	https://doi.org/10.1021/ma1009319
Publication status	Published - 12 Oct 2010

Scopus Subject Areas

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials Chemistry

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10.1021/ma1009319

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Goudreault, T., He, Z., Guo, Y., Ho, C. L., Zhan, H., Wang, Q., Ho, K. Y. F., Wong, K. L., Fortin, D., Yao, B., Xie, Z., Wang, L., Kwok, W. M., Harvey, P. D., & Wong, W. Y. (2010). Synthesis, light-emitting, and two-photon absorption properties of platinum-containing poly(arylene-ethynylene)s linked by 1,3,4-oxadiazole units. Macromolecules, 43(19), 7936-7949. https://doi.org/10.1021/ma1009319

@article{6c6c6e77e6f443b7a570425295346a44,

title = "Synthesis, light-emitting, and two-photon absorption properties of platinum-containing poly(arylene-ethynylene)s linked by 1,3,4-oxadiazole units",

abstract = "A series of soluble and thermally stable group 10 platinum(II) polyyne polymers of the type [-C≡C-Pt(PBu3)2-C≡C-Ar- Ox-Ar-]n (where Ox = 1,3,4-oxadiazole; Ar = p-C6H 4 or 2,7-dihexyl-9,9-fluorene) and [-C≡C-Pt(PBu 3)2-C≡C-Ar-Ox-Ar-Ox-Ar-]n (where Ar = 2,7-dihexyl-9,9-fluorene) along with their corresponding dinuclear model compounds [Ph-Pt(PEt3)2-C≡C-Ar-]2-Ox- (where Ar = p-C6H4 or 2,7-dihexyl-9,9-fluorene) and [Ph-Pt(PEt3)2-C≡C-Ar-Ox-]2-Ar- (where Ar = 2,7-dihexyl-9,9-fluorene) were prepared and characterized. The regiochemical structure of the polymers has been ascertained by single-crystal X-ray analysis on the model compound [Ph-Pt(PEt3)2-C≡C-p-C 6H4-]2-Ox-. The photophysical properties (absorption, excitation, emission, and nanosecond transient absorption spectra) of these metalated compounds in 2MeTHF at 298 and 77 K are reported. These findings are correlated by density functional theory (DFT) calculations. Geometry optimizations predict totally planar molecules for these metalated complexes and polymers, allowing better π-conjugation across the main chain. The ligands are strongly fluorescent but become also phosphorescent when the Pt atom is introduced in the backbone of the conjugated organometallic complexes and polymers. These emissions are assigned to ππ* transitions in all cases involving the Pt dxy orbitals. These Pt compounds exhibit two-photon absorption (2PA), and their 2PA cross sections (σ2) have been determined. The potential of exploiting such metallopolymers for the design of electrophosphorescent polymer light-emitting devices (PLEDs) and their use as single-dopant for white PLEDs have also been discussed.",

author = "Thomas Goudreault and Ze He and Yanhe Guo and Ho, {Cheuk Lam} and Hongmei Zhan and Qiwei Wang and Ho, {Keith Yat Fung} and Wong, {Ka Leung} and Daniel Fortin and Bing Yao and Zhiyuan Xie and Lixiang Wang and Kwok, {Wai Ming} and Harvey, {Pierre D.} and Wong, {Wai Yeung}",

note = "This research was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC), Le Fonds Qu{\'e}b{\'e}cois de la Recherche sur la Nature et les Technologies (FQRNT), and the Centre d'{\'E}tudes des Mat{\'e}riaux Optiques et Photoniques de l'Universit{\'e} de Sherbrooke. W.-Y.W. acknowledges the support from a GRF grant from the Hong Kong Research Grants Council (grant no: HKBU 202709), a FRG grant from Hong Kong Baptist University (FRG2/08-09/111), and the Croucher Senior Research Fellowship from the Croucher Foundation. The work was also supported by State Administration of Foreign Experts Affairs International Partnership Program for Creative Research Teams, Chinese Academy of Sciences.",

year = "2010",

month = oct,

day = "12",

doi = "10.1021/ma1009319",

language = "English",

volume = "43",

pages = "7936--7949",

journal = "Macromolecules",

issn = "0024-9297",

publisher = "American Chemical Society",

number = "19",

}

Goudreault, T, He, Z, Guo, Y, Ho, CL, Zhan, H, Wang, Q, Ho, KYF, Wong, KL, Fortin, D, Yao, B, Xie, Z, Wang, L, Kwok, WM, Harvey, PD & Wong, WY 2010, 'Synthesis, light-emitting, and two-photon absorption properties of platinum-containing poly(arylene-ethynylene)s linked by 1,3,4-oxadiazole units', Macromolecules, vol. 43, no. 19, pp. 7936-7949. https://doi.org/10.1021/ma1009319

TY - JOUR

T1 - Synthesis, light-emitting, and two-photon absorption properties of platinum-containing poly(arylene-ethynylene)s linked by 1,3,4-oxadiazole units

AU - Goudreault, Thomas

AU - He, Ze

AU - Guo, Yanhe

AU - Ho, Cheuk Lam

AU - Zhan, Hongmei

AU - Wang, Qiwei

AU - Ho, Keith Yat Fung

AU - Wong, Ka Leung

AU - Fortin, Daniel

AU - Yao, Bing

AU - Xie, Zhiyuan

AU - Wang, Lixiang

AU - Kwok, Wai Ming

AU - Harvey, Pierre D.

AU - Wong, Wai Yeung

N1 - This research was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC), Le Fonds Québécois de la Recherche sur la Nature et les Technologies (FQRNT), and the Centre d'Études des Matériaux Optiques et Photoniques de l'Université de Sherbrooke. W.-Y.W. acknowledges the support from a GRF grant from the Hong Kong Research Grants Council (grant no: HKBU 202709), a FRG grant from Hong Kong Baptist University (FRG2/08-09/111), and the Croucher Senior Research Fellowship from the Croucher Foundation. The work was also supported by State Administration of Foreign Experts Affairs International Partnership Program for Creative Research Teams, Chinese Academy of Sciences.

PY - 2010/10/12

Y1 - 2010/10/12

N2 - A series of soluble and thermally stable group 10 platinum(II) polyyne polymers of the type [-C≡C-Pt(PBu3)2-C≡C-Ar- Ox-Ar-]n (where Ox = 1,3,4-oxadiazole; Ar = p-C6H 4 or 2,7-dihexyl-9,9-fluorene) and [-C≡C-Pt(PBu 3)2-C≡C-Ar-Ox-Ar-Ox-Ar-]n (where Ar = 2,7-dihexyl-9,9-fluorene) along with their corresponding dinuclear model compounds [Ph-Pt(PEt3)2-C≡C-Ar-]2-Ox- (where Ar = p-C6H4 or 2,7-dihexyl-9,9-fluorene) and [Ph-Pt(PEt3)2-C≡C-Ar-Ox-]2-Ar- (where Ar = 2,7-dihexyl-9,9-fluorene) were prepared and characterized. The regiochemical structure of the polymers has been ascertained by single-crystal X-ray analysis on the model compound [Ph-Pt(PEt3)2-C≡C-p-C 6H4-]2-Ox-. The photophysical properties (absorption, excitation, emission, and nanosecond transient absorption spectra) of these metalated compounds in 2MeTHF at 298 and 77 K are reported. These findings are correlated by density functional theory (DFT) calculations. Geometry optimizations predict totally planar molecules for these metalated complexes and polymers, allowing better π-conjugation across the main chain. The ligands are strongly fluorescent but become also phosphorescent when the Pt atom is introduced in the backbone of the conjugated organometallic complexes and polymers. These emissions are assigned to ππ* transitions in all cases involving the Pt dxy orbitals. These Pt compounds exhibit two-photon absorption (2PA), and their 2PA cross sections (σ2) have been determined. The potential of exploiting such metallopolymers for the design of electrophosphorescent polymer light-emitting devices (PLEDs) and their use as single-dopant for white PLEDs have also been discussed.

AB - A series of soluble and thermally stable group 10 platinum(II) polyyne polymers of the type [-C≡C-Pt(PBu3)2-C≡C-Ar- Ox-Ar-]n (where Ox = 1,3,4-oxadiazole; Ar = p-C6H 4 or 2,7-dihexyl-9,9-fluorene) and [-C≡C-Pt(PBu 3)2-C≡C-Ar-Ox-Ar-Ox-Ar-]n (where Ar = 2,7-dihexyl-9,9-fluorene) along with their corresponding dinuclear model compounds [Ph-Pt(PEt3)2-C≡C-Ar-]2-Ox- (where Ar = p-C6H4 or 2,7-dihexyl-9,9-fluorene) and [Ph-Pt(PEt3)2-C≡C-Ar-Ox-]2-Ar- (where Ar = 2,7-dihexyl-9,9-fluorene) were prepared and characterized. The regiochemical structure of the polymers has been ascertained by single-crystal X-ray analysis on the model compound [Ph-Pt(PEt3)2-C≡C-p-C 6H4-]2-Ox-. The photophysical properties (absorption, excitation, emission, and nanosecond transient absorption spectra) of these metalated compounds in 2MeTHF at 298 and 77 K are reported. These findings are correlated by density functional theory (DFT) calculations. Geometry optimizations predict totally planar molecules for these metalated complexes and polymers, allowing better π-conjugation across the main chain. The ligands are strongly fluorescent but become also phosphorescent when the Pt atom is introduced in the backbone of the conjugated organometallic complexes and polymers. These emissions are assigned to ππ* transitions in all cases involving the Pt dxy orbitals. These Pt compounds exhibit two-photon absorption (2PA), and their 2PA cross sections (σ2) have been determined. The potential of exploiting such metallopolymers for the design of electrophosphorescent polymer light-emitting devices (PLEDs) and their use as single-dopant for white PLEDs have also been discussed.

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U2 - 10.1021/ma1009319

DO - 10.1021/ma1009319

M3 - Journal article

AN - SCOPUS:77957773146

SN - 0024-9297

VL - 43

SP - 7936

EP - 7949

JO - Macromolecules

JF - Macromolecules

IS - 19

ER -

Synthesis, light-emitting, and two-photon absorption properties of platinum-containing poly(arylene-ethynylene)s linked by 1,3,4-oxadiazole units

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