Dicopper(I) Complexes Incorporating Acetylide-Functionalized Pyridinyl-Based Ligands: Synthesis, Structural, and Photovoltaic Studies
Heteroaryl incorporated acetylide-functionalized pyridinyl ligands (L1–L6) with the general formula Py-CC-Ar (Py = pyridine and Ar = thiophene-2-yl, 2,2′-bithiophene]-5-yl, 2,2′:5′,2″-terthiophene]-5-yl, thieno[2,3-b]thiophen-2-yl, quinoline-5-yl, benzo[c][1,2,5]thiadiazole-5-yl) have been syn...
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| Published in | Inorganic chemistry Vol. 57; no. 19; pp. 12113 - 12124 |
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| Main Authors | , , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
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United States
American Chemical Society
01.10.2018
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| Abstract | Heteroaryl incorporated acetylide-functionalized pyridinyl ligands (L1–L6) with the general formula Py-CC-Ar (Py = pyridine and Ar = thiophene-2-yl, 2,2′-bithiophene]-5-yl, 2,2′:5′,2″-terthiophene]-5-yl, thieno[2,3-b]thiophen-2-yl, quinoline-5-yl, benzo[c][1,2,5]thiadiazole-5-yl) have been synthesized by Pd(0)/Cu(I)-catalyzed cross-coupling reaction of 4-ethynylpyridine and the respective heteroaryl halide. Ligands L1–L6 were isolated in respectable yields and characterized by microanalysis, IR spectroscopy, 1H NMR spectroscopy, and ESI-MS mass spectrometry. A series of dinuclear Cu(I) complexes 1–10 have been synthesized by reacting L1–L6 with CuI and triphenylphosphine (PPh3) (R1) or with an anchored phosphine derivative, 4-(diphenylphosphino) benzoic acid (R2)/2-(diphenylphosphino)benzenesulfonic acid (R3), in a stoichiometric ratio. The complexes are soluble in common organic solvents and have been characterized by analytical, spectroscopic, and computational methods. Single-crystal X-ray structure analysis confirmed rhomboid dimeric structures for complexes 1, 2, 4, and 5, and a polymeric structure for 6. Complexes 1–6 showed oxidation potential responses close to 0.9 V vs Fc0/+, which were chemically irreversible and are likely to be associated with multiple steps and core oxidation. Preliminary photovoltaic (PV) results of these new materials indicated moderate power conversion efficiency (PCE) in the range of 0.15–1.56% in dye-sensitized solar cells (DSSCs). The highest PCE was achieved with complex 10 bearing the sulfonic acid anchoring functionality. |
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| AbstractList | Heteroaryl incorporated acetylide-functionalized pyridinyl ligands (L1-L6) with the general formula Py-C≡C-Ar (Py = pyridine and Ar = thiophene-2-yl, 2,2' -bithiophene]-5-yl, 2,2' :5',2″ -terthiophene]-5-yl, thieno[2,3- b]thiophen-2-yl, quinoline-5-yl, benzo[c][1,2,5]thiadiazole-5-yl) have been synthesized by Pd(0)/Cu(I)-catalyzed cross-coupling reaction of 4-ethynylpyridine and the respective heteroaryl halide. Ligands L1-L6 were isolated in respectable yields and characterized by microanalysis, IR spectroscopy, 1H NMR spectroscopy, and ESI-MS mass spectrometry. A series of dinuclear Cu(I) complexes 1-10 have been synthesized by reacting L1-L6 with CuI and triphenylphosphine (PPh3) (R1) or with an anchored phosphine derivative, 4-(diphenylphosphino) benzoic acid (R2)/2-(diphenylphosphino)benzenesulfonic acid (R3), in a stoichiometric ratio. The complexes are soluble in common organic solvents and have been characterized by analytical, spectroscopic, and computational methods. Single-crystal X-ray structure analysis confirmed rhomboid dimeric structures for complexes 1, 2, 4, and 5, and a polymeric structure for 6. Complexes 1-6 showed oxidation potential responses close to 0.9 V vs Fc0/+, which were chemically irreversible and are likely to be associated with multiple steps and core oxidation. Preliminary photovoltaic (PV) results of these new materials indicated moderate power conversion efficiency (PCE) in the range of 0.15-1.56% in dye-sensitized solar cells (DSSCs). The highest PCE was achieved with complex 10 bearing the sulfonic acid anchoring functionality.Heteroaryl incorporated acetylide-functionalized pyridinyl ligands (L1-L6) with the general formula Py-C≡C-Ar (Py = pyridine and Ar = thiophene-2-yl, 2,2' -bithiophene]-5-yl, 2,2' :5',2″ -terthiophene]-5-yl, thieno[2,3- b]thiophen-2-yl, quinoline-5-yl, benzo[c][1,2,5]thiadiazole-5-yl) have been synthesized by Pd(0)/Cu(I)-catalyzed cross-coupling reaction of 4-ethynylpyridine and the respective heteroaryl halide. Ligands L1-L6 were isolated in respectable yields and characterized by microanalysis, IR spectroscopy, 1H NMR spectroscopy, and ESI-MS mass spectrometry. A series of dinuclear Cu(I) complexes 1-10 have been synthesized by reacting L1-L6 with CuI and triphenylphosphine (PPh3) (R1) or with an anchored phosphine derivative, 4-(diphenylphosphino) benzoic acid (R2)/2-(diphenylphosphino)benzenesulfonic acid (R3), in a stoichiometric ratio. The complexes are soluble in common organic solvents and have been characterized by analytical, spectroscopic, and computational methods. Single-crystal X-ray structure analysis confirmed rhomboid dimeric structures for complexes 1, 2, 4, and 5, and a polymeric structure for 6. Complexes 1-6 showed oxidation potential responses close to 0.9 V vs Fc0/+, which were chemically irreversible and are likely to be associated with multiple steps and core oxidation. Preliminary photovoltaic (PV) results of these new materials indicated moderate power conversion efficiency (PCE) in the range of 0.15-1.56% in dye-sensitized solar cells (DSSCs). The highest PCE was achieved with complex 10 bearing the sulfonic acid anchoring functionality. Heteroaryl incorporated acetylide-functionalized pyridinyl ligands (L1-L6) with the general formula Py-C≡C-Ar (Py = pyridine and Ar = thiophene-2-yl, 2,2' -bithiophene]-5-yl, 2,2' :5',2″ -terthiophene]-5-yl, thieno[2,3- b]thiophen-2-yl, quinoline-5-yl, benzo[c][1,2,5]thiadiazole-5-yl) have been synthesized by Pd(0)/Cu(I)-catalyzed cross-coupling reaction of 4-ethynylpyridine and the respective heteroaryl halide. Ligands L1-L6 were isolated in respectable yields and characterized by microanalysis, IR spectroscopy, H NMR spectroscopy, and ESI-MS mass spectrometry. A series of dinuclear Cu(I) complexes 1-10 have been synthesized by reacting L1-L6 with CuI and triphenylphosphine (PPh ) (R1) or with an anchored phosphine derivative, 4-(diphenylphosphino) benzoic acid (R2)/2-(diphenylphosphino)benzenesulfonic acid (R3), in a stoichiometric ratio. The complexes are soluble in common organic solvents and have been characterized by analytical, spectroscopic, and computational methods. Single-crystal X-ray structure analysis confirmed rhomboid dimeric structures for complexes 1, 2, 4, and 5, and a polymeric structure for 6. Complexes 1-6 showed oxidation potential responses close to 0.9 V vs Fc , which were chemically irreversible and are likely to be associated with multiple steps and core oxidation. Preliminary photovoltaic (PV) results of these new materials indicated moderate power conversion efficiency (PCE) in the range of 0.15-1.56% in dye-sensitized solar cells (DSSCs). The highest PCE was achieved with complex 10 bearing the sulfonic acid anchoring functionality. Heteroaryl incorporated acetylide-functionalized pyridinyl ligands (L1–L6) with the general formula Py-CC-Ar (Py = pyridine and Ar = thiophene-2-yl, 2,2′-bithiophene]-5-yl, 2,2′:5′,2″-terthiophene]-5-yl, thieno[2,3-b]thiophen-2-yl, quinoline-5-yl, benzo[c][1,2,5]thiadiazole-5-yl) have been synthesized by Pd(0)/Cu(I)-catalyzed cross-coupling reaction of 4-ethynylpyridine and the respective heteroaryl halide. Ligands L1–L6 were isolated in respectable yields and characterized by microanalysis, IR spectroscopy, 1H NMR spectroscopy, and ESI-MS mass spectrometry. A series of dinuclear Cu(I) complexes 1–10 have been synthesized by reacting L1–L6 with CuI and triphenylphosphine (PPh3) (R1) or with an anchored phosphine derivative, 4-(diphenylphosphino) benzoic acid (R2)/2-(diphenylphosphino)benzenesulfonic acid (R3), in a stoichiometric ratio. The complexes are soluble in common organic solvents and have been characterized by analytical, spectroscopic, and computational methods. Single-crystal X-ray structure analysis confirmed rhomboid dimeric structures for complexes 1, 2, 4, and 5, and a polymeric structure for 6. Complexes 1–6 showed oxidation potential responses close to 0.9 V vs Fc0/+, which were chemically irreversible and are likely to be associated with multiple steps and core oxidation. Preliminary photovoltaic (PV) results of these new materials indicated moderate power conversion efficiency (PCE) in the range of 0.15–1.56% in dye-sensitized solar cells (DSSCs). The highest PCE was achieved with complex 10 bearing the sulfonic acid anchoring functionality. |
| Author | Khan, Muhammad S Jayapal, Maharaja Islam, Shahidul M Marken, Frank Xin, Chenghao Raithby, Paul R Haque, Ashanul Wong, Wai-Yeung Al-Suti, Mohammed K Al-Balushi, Rayya Wu, Wenjun Al-Rasbi, Nawal Al-Busaidi, Idris J |
| AuthorAffiliation | Department of Chemistry Department of Basic Sciences, College of Applied and Health Sciences A’Sharqiyah University The Hong Kong Polytechnic University University of Illinois at Chicago Institute of Molecular Functional Materials and Department of Applied Biology and Chemical Technology Key Laboratory for Advanced Materials and Institute of Fine Chemicals, Centre for Computational Chemistry, Shanghai Key Laboratory of Functional Materials Chemistry, School of Chemistry and Molecular Engineering |
| AuthorAffiliation_xml | – name: Department of Chemistry – name: Department of Basic Sciences, College of Applied and Health Sciences – name: Institute of Molecular Functional Materials and Department of Applied Biology and Chemical Technology – name: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, Centre for Computational Chemistry, Shanghai Key Laboratory of Functional Materials Chemistry, School of Chemistry and Molecular Engineering – name: The Hong Kong Polytechnic University – name: A’Sharqiyah University – name: University of Illinois at Chicago |
| Author_xml | – sequence: 1 givenname: Maharaja surname: Jayapal fullname: Jayapal, Maharaja organization: Department of Chemistry – sequence: 2 givenname: Ashanul orcidid: 0000-0002-6780-632X surname: Haque fullname: Haque, Ashanul organization: Department of Chemistry – sequence: 3 givenname: Idris J surname: Al-Busaidi fullname: Al-Busaidi, Idris J organization: Department of Chemistry – sequence: 4 givenname: Nawal surname: Al-Rasbi fullname: Al-Rasbi, Nawal organization: Department of Chemistry – sequence: 5 givenname: Mohammed K surname: Al-Suti fullname: Al-Suti, Mohammed K organization: Department of Chemistry – sequence: 6 givenname: Muhammad S surname: Khan fullname: Khan, Muhammad S email: msk@squ.edu.om organization: Department of Chemistry – sequence: 7 givenname: Rayya surname: Al-Balushi fullname: Al-Balushi, Rayya organization: A’Sharqiyah University – sequence: 8 givenname: Shahidul M surname: Islam fullname: Islam, Shahidul M email: mshahidi@uic.edu organization: University of Illinois at Chicago – sequence: 9 givenname: Chenghao surname: Xin fullname: Xin, Chenghao organization: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, Centre for Computational Chemistry, Shanghai Key Laboratory of Functional Materials Chemistry, School of Chemistry and Molecular Engineering – sequence: 10 givenname: Wenjun orcidid: 0000-0003-0044-1917 surname: Wu fullname: Wu, Wenjun organization: Key Laboratory for Advanced Materials and Institute of Fine Chemicals, Centre for Computational Chemistry, Shanghai Key Laboratory of Functional Materials Chemistry, School of Chemistry and Molecular Engineering – sequence: 11 givenname: Wai-Yeung orcidid: 0000-0002-9949-7525 surname: Wong fullname: Wong, Wai-Yeung email: wai-yeung.wong@polyu.edu.hk organization: The Hong Kong Polytechnic University – sequence: 12 givenname: Frank orcidid: 0000-0003-3177-4562 surname: Marken fullname: Marken, Frank email: f.marken@bath.ac.uk organization: Department of Chemistry – sequence: 13 givenname: Paul R orcidid: 0000-0002-2944-0662 surname: Raithby fullname: Raithby, Paul R email: p.r.raithby@bath.ac.uk organization: Department of Chemistry |
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| Snippet | Heteroaryl incorporated acetylide-functionalized pyridinyl ligands (L1–L6) with the general formula Py-CC-Ar (Py = pyridine and Ar = thiophene-2-yl,... Heteroaryl incorporated acetylide-functionalized pyridinyl ligands (L1-L6) with the general formula Py-C≡C-Ar (Py = pyridine and Ar = thiophene-2-yl, 2,2'... |
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| Title | Dicopper(I) Complexes Incorporating Acetylide-Functionalized Pyridinyl-Based Ligands: Synthesis, Structural, and Photovoltaic Studies |
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