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

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

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9 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)12113-12124
Number of pages12
JournalInorganic Chemistry
Volume57
Issue number19
DOIs
Publication statusPublished - Oct 1 2018

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry

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    Jayapal, M., Haque, A., Al-Busaidi, I. J., Al-Rasbi, N., Al-Suti, M. K., Khan, M., Al-Balushi, R., Islam, S. M., Xin, C., Wu, W., Wong, W. Y., Marken, F., & Raithby, P. R. (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