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Dalton Transactions
DOI: 10.1039/C7DT00575J
13C NMR (CD3CN): δ 150.5, 120.6, 92.8, 61.7, 44.4, 15.5, 8.2. Anal. Calcd. for
[(η5ꢀC5Me5)Ir(L2)Cl]PF6 (712.15): C, 35.42; H, 4.39; N, 7.87. Found: C, 35.49; H, 4.35; N, 7.94.
MS: m/z 567.6 [(η5ꢀC5Me5)Ir(L2)Cl]+.
[(η5-C5Me4C6H5)Ir(L2)Cl]PF6 (2B). Yield: 30.6 mg, 39.6%. IR (KBr pellets, cmꢀ1): 1475
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(υC=N), 840 (υP–F). H NMR (500.13 MHz, CD3CN): δ 7.38 (m, J = 2.1 Hz, 5H), 7.32 (d, J = 1.6
Hz, 2H), 7.28 (s, 2H), 6.00 – 5.54 (s, 2H), 4.11 (q, J = 7.3Hz, 2H), 3.81 (q, J = 7.1 Hz, 2H), 1.84
(s, 6H), 1.79 (s, 6H), 1.23 (s , 6H). 13C NMR (CD3CN): δ 149.1, 128.2, 120.8, 92.8, 61.8, 44.4,
15.1, 8.5. Anal. Calcd. for [(η5ꢀC5Me4C6H5)Ir(L2)Cl]PF6 (774.17): C, 40.34; H, 4.30; N, 7.24.
Found: C, 40.41; H, 4.28; N, 7.29. MS: m/z 629.6 [(η5ꢀC5Me4C6H5)Ir(L2)Cl]+.
[(η5-C5Me4C6H4C6H5)Ir(L2)Cl]PF6 (2C). Yield: 30.1 mg, 35.4%. IR (KBr pellets, cmꢀ1):
1467 (υC=N), 840 (υP–F). 1H NMR (500.13 MHz, CD3CN): δ 7.66 (m, 4H), 7.49 (m, 2H), 7.41 (m,
5H), 7.30 (d, J = 2.1 Hz, 2H), 6.01 – 5.55 (s, 2H), 4.14 (q, J = 7.3 Hz, 2H), 3.83 (q, J = 7.1 Hz,
2H), 1.88 (s, 6H), 1.85 (s, 6H), 1.25 (s, 6H). 13C NMR (CD3CN): δ 149.0, 139.6, 128.7, 120.8,
93.1, 61.8, 44.5, 15.1, 8.6. Anal. Calcd. for [(η5ꢀC5Me4C6H4C6H5)Ir(L2)Cl]PF6 (850.20): C, 45.20;
H, 4.39; N, 6.59. Found: C, 45.07; H, 4.36; N, 6.55. MS: m/z 705.7
[(η5ꢀC5Me4C6H4C6H5)Ir(L2)Cl]+.
[(η5-C5Me5)Ir(L3)Cl]PF6 (3A). Yield: 25.7 mg, 33.4%. IR (KBr pellets, cmꢀ1): 1470 (υC=N),
842 (υP–F). 1H NMR (500.13 MHz, CD3CN): δ 7.34 (s, 2H), 7.30 (s, 2H), 5.96 – 5.48 (s, 2H), 4.21
(t, J = 5.2 Hz, 2H), 3.94 – 3.87 (m, 2H), 1.75 (s, 15H), 1.72 (m, 4H), 1.28 (dq, J = 14.5, 7.4Hz,
4H), 0.95 (t, J = 7.4 Hz, 6H). 13C NMR (CD3CN): δ 150.4, 120.9, 92.8, 61.7, 49.3, 32.8, 19.5, 12.8,
8.2. Anal. Calcd. for [(η5ꢀC5Me5)Ir(L3)Cl]PF6 (768.21): C, 39.09; H, 5.12; N, 7.29. Found: C,
39.17; H, 5.09; N, 7.20. MS: m/z 623.7 [(η5ꢀC5Me5)Ir(L3)Cl]+.
[(η5-C5Me4C6H5)Ir(L3)Cl]PF6 (3B). Yield: 23.9 mg, 28.9%. IR (KBr pellets, cmꢀ1): 1473
(υC=N), 840 (υP–F). 1H NMR (500.13 MHz, CD3CN): δ 7.37 (m, 7H), 7.28 (s, 2H), 6.00 – 5.55 (s,
2H), 4.10 – 4.03 (m, 2H), 3.69 – 3.62 (m, 2H), 1.85 (s, 6H), 1.82 (s, 6H), 1.65 (m, 4H), 1.23 (dq, J
= 14.9, 7.3 Hz, 4H), 0.86 (t, J = 7.4 Hz, 6H). 13C NMR (CD3CN): δ 148.9, 128.3, 121.1, 92.5, 61.8,
49.3, 32.5, 19.3, 12.8, 8.6. Anal. Calcd. for [(η5ꢀC5Me4C6H5)Ir(L3)Cl]PF6 (830.23): C, 43.40; H,
4.98; N, 6.75. Found: C, 43.49; H, 4.91; N, 6.73. MS: m/z 685.8 [(η5ꢀC5Me4C6H5)Ir(L3)Cl]+.
[(η5-C5Me4C6H4C6H5)Ir(L3)Cl]PF6 (3C). Yield: 23.0 mg, 25.4%. IR (KBr pellets, cmꢀ1):
1474 (υC=N), 839 (υP–F). 1H NMR (500.13 MHz, CD3CN): δ 7.67 (m, 4H), 7.50 (m, 4H), 7.38 (m,
3H), 7.28 (s, 2H), 6.01 – 5.57 (s, 2H), 4.10 – 4.03 (m, 2H), 3.70 (s, 2H), 1.90 (s, 6H), 1.83 (s, 6H),
1.65 (m, 4H), 1.22 (dq, J = 14.9, 7.3 Hz, 4H), 0.84 (t, J = 7.4 Hz, 6H). 13C NMR (CD3CN): δ
148.8, 139.7, 128.7, 121.1, 91.9, 61.8, 49.3, 32.5, 19.3, 12.8, 8.7. Anal. Calcd. for
[(η5ꢀC5Me4C6H4C6H5)Ir(L3)Cl]PF6 (906.26): C, 47.70; H, 5.00; N, 6.18. Found: C, 47.76; H,4.97;
N, 6.10. MS: m/z 761.8 [(η5ꢀC5Me4C6H4C6H5)Ir(L3)Cl]+.
[(η5-C5Me5)Ir(L4)Cl]PF6 (4A). Yield: 21 mg, 26.0%. IR (KBr pellets, cmꢀ1): 1471 (υC=N),
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837 (υP–F). H NMR (500.13 MHz, CD3CN): δ 7.92 (s, 2H), 7.54 – 7.48 (m, 10H), 7.36 (s, 2H),
6.15 – 5.63 (s, 2H), 1.25 (s, 15H). 13C NMR (CD3CN): δ 150.3, 138.4, 121.3, 99.5, 62.8, 8.2. Anal.
Calcd. for [(η5ꢀC5Me5)Ir(L4)Cl]PF6 (808.15): C, 43.10; H, 3.87; N, 6.93. Found: C, 43.19; H, 3.90;
N, 6.85. MS: m/z 663.7 [(η5ꢀC5Me5)Ir(L4)Cl]+.
[(η5-C5Me4C6H5)Ir(L4)Cl]PF6 (4B). Yield: 20.6 mg, 23.7%. IR (KBr pellets, cmꢀ1): 1471
(υC=N), 835 (υP–F). 1H NMR (500.13 MHz, CD3CN): δ 7.59 (s, 2H), 7.36 – 7.29 (m, 15H), 6.90 (s,
2H), 6.26 – 5.81 (s, 2H), 1.33 (s, 6H), 1.26 (s, 6H). 13C NMR (CD3CN): δ 148.8, 138.5, 127.8,
121.3, 99.2, 62.8, 8.4. Anal. Calcd for [(η5ꢀC5Me4C6H5)Ir(L4)Cl]PF6 (870.17): C, 46.92; H, 3.82;
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