Dicopper(I) Complexes Incorporating Acetylide-functionalized Pyridinyl-based Ligands: Synthesis, Structural and Photovoltaic Studies

Jayapal Maharaja, Ashanul Haque, Idris Juma Al-Busaidi, Nawal A-Rasbi, Mohammed K Al-Suti, Muhammad S Khan, Rayya A. Al-Balushi, Shahidul Islam, Chenghao Xin, Wenjun Wu, Wai-Yeung Wong, Frank Marken, Paul Raithby

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Abstract

Hetero-aryl incorporated acetylide-functionalized pyridinyl ligands (L1-6) 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. 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-(diphenyl phosphino) 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.
Original languageEnglish
Pages (from-to)12113-12124
Number of pages12
JournalInorganic Chemistry
Volume57
Issue number19
Early online date17 Sep 2018
DOIs
Publication statusPublished - 1 Oct 2018

Keywords

  • copper compounds
  • Acetylide
  • Pyridynyl
  • x-ray crystal structure
  • Photovoltaic

ASJC Scopus subject areas

  • Inorganic Chemistry

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    Maharaja, J., Haque, A., Al-Busaidi, I. J., A-Rasbi, N., Al-Suti, M. K., Khan, M. S., Al-Balushi, R. A., Islam, S., Xin, C., Wu, W., Wong, W-Y., Marken, F., & Raithby, P. (2018). Dicopper(I) Complexes Incorporating Acetylide-functionalized Pyridinyl-based Ligands: Synthesis, Structural and Photovoltaic Studies. Inorganic Chemistry, 57(19), 12113-12124. https://doi.org/10.1021/acs.inorgchem.8b01684