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

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › 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. © 2010 American Chemical Society.

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

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Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected].

Funding

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.

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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{bfcfbcb58b8e4d348741e113be77764c,

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. {\textcopyright} 2010 American Chemical Society.",

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

note = "Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected].",

year = "2010",

month = oct,

day = "12",

doi = "10.1021/ma1009319",

language = "English",

volume = "43",

pages = "7936--7949",

journal = "Macromolecules",

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publisher = "American Chemical Society",

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Goudreault, T, He, Z, Guo, Y, Ho, C-L, Zhan, H, Wang, Q, Ho, KY-F, Wong, K-L, Fortin, D, Yao, B, Xie, Z, Wang, L, Kwok, W-M, Harvey, PD & 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, 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 - Publication details (e.g. title, author(s), publication statuses and dates) are captured on an “AS IS” and “AS AVAILABLE” basis at the time of record harvesting from the data source. Suggestions for further amendments or supplementary information can be sent to [email protected].

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. © 2010 American Chemical Society.

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. © 2010 American Chemical Society.

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U2 - 10.1021/ma1009319

DO - 10.1021/ma1009319

M3 - RGC 21 - Publication in refereed journal

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

Abstract

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