TY - JOUR
T1 - Dicopper(I) Complexes Incorporating Acetylide-Functionalized Pyridinyl-Based Ligands
T2 - Synthesis, Structural, and Photovoltaic Studies
AU - Jayapal, Maharaja
AU - Haque, Ashanul
AU - Al-Busaidi, Idris J.
AU - Al-Rasbi, Nawal
AU - Al-Suti, Mohammed K.
AU - Khan, Muhammad S.
AU - Al-Balushi, Rayya
AU - Islam, Shahidul M.
AU - Xin, Chenghao
AU - Wu, Wenjun
AU - Wong, Wai Yeung
AU - Marken, Frank
AU - Raithby, Paul R.
PY - 2018/10/1
Y1 - 2018/10/1
N2 -
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,
1
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
3
) (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
0/+
, 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.
AB -
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,
1
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
3
) (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
0/+
, 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.
UR - http://www.scopus.com/inward/record.url?scp=85053669261&partnerID=8YFLogxK
U2 - 10.1021/acs.inorgchem.8b01684
DO - 10.1021/acs.inorgchem.8b01684
M3 - Journal article
C2 - 30222331
AN - SCOPUS:85053669261
SN - 0020-1669
VL - 57
SP - 12113
EP - 12124
JO - Inorganic Chemistry
JF - Inorganic Chemistry
IS - 19
ER -
