S. Gladiali, M. Beller et al.
J=8.0 Hz, 1H), 8.30–8.24 (m, 4H), 8.06 (d, J=5.3 Hz, 1H), 7.97–7.81 (m,
4H), 7.74–7.71 (m, 2H), 7.50 (d, J=6.2 Hz, 1H), 7.21–7.16 (m, 1H),
7.12–7.08 (m, 1H), 7.05–6.99 (m, 1H), 6.91–6.86 (m, 2H), 6.73 (t, J=
7.5 Hz, 1H), 6.07 (d, J=7.3 Hz, 1H), 5.98 ppm (d, J=7.7 Hz, 1H);
13C NMR (100 MHz, [D6]DMSO): d=167.6, 165.9, 158.1, 154.7, 150.6,
150.4, 149.6, 148.7, 147.0, 143.7, 143.2, 141.0, 139.9, 139.0, 135.8, 134.8,
131.9, 130.5, 130.1, 130.1, 129.2, 128.4, 126.3, 125.1, 125.0, 124.2, 124.1,
123.4, 122.8, 122.2, 120.2, 119.9, 113.7 ppm (-CN); ATR-IR: n˜ =3043 (w),
1607 (w), 1583 (w), 1479 (w), 1446 (w), 1165(w), 836 (s), 759 (m), 736
(m), 556 cmÀ1 (m); HRMS (ESI): m/z calcd for [C33H23IrN5]+: 682.1579;
found: 682.1588 [M]+.
[D6]DMSO): d=9.72 (d, J=0.7 Hz, 1H), 8.95 (d, J=8.0 Hz, 1H), 8.46 (d,
J=0.7 Hz, 1H), 8.40–8.36 (m, 1H), 8.28–8.26 (m, 2H), 8.20–8.19 (m,
1H), 7.99–7.91 (m, 6H), 7.64–7.62 (m, 1H), 7.20–7.13 (m, 2H), 7.06–7.01
(m, 2H), 6.91 (dt, J=1.0, 7.4 Hz, 2H), 6.21 (d, J=7.6 Hz, 1H), 6.14 ppm
(d, J=7.5 Hz, 1H); 13C NMR (75 MHz, [D6]DMSO): d=171. 6, 167.3,
166.5, 166.3, 165.2, 151.0, 150.3, 150.8, 149.8, 148.8, 146.8, 144.0, 143.8,
140.4, 139.0, 132.6, 131.3, 130.8, 130.3, 130.2, 128.6, 125.1, 124.1, 123.8,
122.7, 122.6, 120.2, 112.0 ppm (several signals in the aromatic region over-
lapped); ATR-IR: n˜ =3045 (w), 1608 (w), 1558 (w), 1527 (w), 1479 (w),
1426 (m), 1387 (w), 1269 (w), 1165 (w), 1031 (w), 836 (s), 756 (m), 738
(w), 661 (w), 556 (m), 418 cmÀ1 (w); HRMS (ESI): m/z calcd for
[C30H22IrN6]+: 657.1506; found: 657.1505 [M]+.
Synthesis of PS4: Prepared by using method A (CH2Cl2, EtOH proce-
dure) to give PS4 as
a
yellow solid (90%). 1H NMR (400 MHz,
Synthesis of PS9: Prepared by using method B (ethylene glycol proce-
dure) to give PS9 as a red solid (76%).1H NMR (300 MHz, [D6]DMSO):
d=9.58 (s, 1H), 8.51 (d, J=7.6 Hz, 1H), 8.46 (d, J=5.0 Hz, 1H), 8.32–
8.27 (m, 2H), 8.09 (d, J=7.9 Hz, 1H), 8.00–7.90 (m, 3H), 7.83–7.75 (m,
2H), 7.62–7.59 (m, 2H), 7.35–7.22 (m, 2H), 7.19–6.98 (m, 4H), 6.94–6.85
(m, 3H), 6.84–6.70 (m, 2H), 6.11 (dd, J=7.6, 0.9 Hz, 1H), 6.02 ppm (dd.
J=7.4, Hz, 1.1 Hz, 1H); 13C NMR (75 MHz, [D6]DMSO): d=169.8,
166.9, 166.5, 155.4, 150.7, 150.1, 149.9, 149.3, 148.7, 147.6, 143.7, 143.4,
139.7, 138.8, 131.2, 130.9, 130.8, 130.4, 130.3, 129.6, 128.5, 128.3, 125.1,
124.5, 124.1, 123.8, 122.5, 122.4, 121.7, 120.1, 119.6 ppm (several signals in
the aromatic region overlapped); ATR-IR: n˜ =3043 (w), 1608 (w), 1584
(w), 1479 (m), 1421 (w), 1269 (w), 1164 (w), 1064 (w), 1031 (w), 836 (s),
757 (m), 738 (m), 693 (w), 556 cmÀ1 (m); HRMS (ESI): m/z: calcd for
[C34H26IrN4]+: 683.1781; found: 683.1783 [M]+.
[D6]DMSO): d=8.86 (d, J=8.0 Hz, 2H), 8.31–8.23 (m, 4H), 8.12 (d, J=
5.5 Hz, 1H), 8.00–7.88 (m, 3H), 7.82–7.78 (m, 2H), 7.73–7.65 (m, 2H),
7.54 (d, J=5.5 Hz, 1H), 7.23 (t, J=6.4 Hz, 1H), 7.13 (t, J=6.4 Hz, 1H),
7.01 (t, J=7.4 Hz, 1H), 6.89–6.84 (m, 2H), 6.74 (t, J=7.3 Hz, 1H), 6.07
(d, J=7.5 Hz, 1H), 5.96 ppm (d, J=7.6 Hz, 1H); 13C NMR (100 MHz,
[D6]DMSO): d=167.6, 165.9, 157.0, 155.9, 154.6, 152.2, 150.8, 149.4,
148.5, 146.1, 143.3, 143.1, 142.4, 139.7, 138.8, 131.5, 130.4, 129.8, 129.2,
129.2, 128.5, 126.0, 125.1, 124.6, 124.1, 123.7, 123.4, 122.6, 121.3, 120.2,
119.8 ppm (several signals in the aromatic region overlapped); ATR-IR:
n˜ =3042 (w), 1607 (w), 1595 (w), 1478 (w), 1436 (w), 1269 (w), 1230 (w),
1166 (w), 1085 (w), 1029 (w), 834 (s), 773 (w), 757 (m), 731 (m), 702 (w),
556 cmÀ1 (m); HRMS (ESI): m/z: calcd for [C32H23IrN4]+: 689.1212;
found: 689.1214 [M]+.
Synthesis of PS5: Prepared by using method A (CH2Cl2, EtOH proce-
dure) to give PS5 as
a
yellow solid (99%). 1H NMR (400 MHz,
Synthesis of PS10: Prepared by using method B to give PS10 as a yellow
solid (90%).1H NMR (300 MHz, [D6]DMSO): d=9.31 (d, J=3.0 Hz,
1H), 8.54 (d, J=8.5 Hz, 1H), 8.36–8.33 (m, 1H), 8.28 (d, J=8.3 Hz, 2H),
7.99–7.87 (m, 4H), 7.78 (d, J=5.8 Hz, 1H), 7.73 (d, J=5.8 Hz, 1H), 7.66
(dd, J=5.6, 1.2 Hz, 1H), 7.56 (dt, J=7.3, 1.0 Hz, 1H), 7.29 (d, J=2.0 Hz,
1H), 7.23–7.19 (m, 2H), 7.02–6.99 (m, 2H), 6.98–6.85 (m, 3H), 6.21–
6.19 ppm (m, 2H); 13C NMR (75 MHz, [D6]DMSO): d=166.8, 166.7,
149.2, 149.2, 149.1, 148.7, 148.2, 146.1, 144.1, 144.0, 143.3, 141.7, 138.9,
138.8, 132.7, 131.3, 131.1, 130.1, 129.7, 125.3, 125.1, 124.7, 123.9, 123.8,
122.3, 122.1, 112.0, 119.9, 113.5, 111.5 ppm; ATR-IR: n˜ =3041 (w), 1610
(w), 1583 (w), 1479 (w), 1409 (w), 1354 (w), 1269 (w), 1067 (w), 881 (w),
834 (s), 776 (w), 755 (s), 729 (w), 670 (w), 556 (s), 416 cmÀ1 (w); HRMS
(ESI): m/z calcd for [C30H23IrN5]+: 646.1577; found: 646.1592 [M]+.
[D6]DMSO): d=8.88–8.85 (m, 2H), 8.34 (t, J=7.9 Hz, 1H), 8.26–8.22
(m, 1H), 8.14–8.09 (m, 2H), 8.00–7.96 (m, 1H), 7.92–7.88 (m, 1H), 7.78
(d, J=5.6 Hz, 1H), 7.74–7.70 (m, 3H), 7.61–7.54 (m, 2H), 7.36 (d, J=
7.4 Hz, 1H), 7.25–7.22 (m, 1H), 7.18–7.15 (m, 1H), 6.93–6.87 (m, 2H),
6.70–6.71 (m, 3H), 6.59–6.49 (m, 3H), 6.30–6.26 (m, 1H), 5.82 (d, J=
7.5 Hz, 1H), 5.43 ppm (d, J=7.6, 1H); 13C NMR (100 MHz, [D6]DMSO):
d=168.0, 166.2, 164.6, 156.7, 156.4, 151.1, 149.7, 149.2, 149.0, 147.0, 143.0,
142.8, 139.8, 139.5, 138.7, 138.4, 138.0, 130.9, 130.3, 129.8, 129.6, 128.8,
128.4, 127.9, 127.4, 127.2, 125.4, 124.7, 124.3, 123.9, 122.8, 122.4, 120.0,
112.0, 119.9 ppm (several signals in the aromatic region overlapped);
ATR-IR: n˜ =3047 (w), 1607 (w), 1582 (w), 1477 (m), 1450 (w), 1423 (w),
1269 (w), 1226 (w), 1169 (w), 1064 (w), 836 (s), 781 (w), 758 (m), 738
(m), 696 (w), 557 cmÀ1 (m); HRMS (ESI): m/z: calcd for [C38H28IrN4]+:
733.1940; found: 733.1939 [M]+.
Synthesis of PS11: Prepared by using method B to give PS11 as a yellow
solid (81%).1H NMR (300 MHz, [D6]DMSO): d=8.94 (s, 1H), 8.38 (d,
J=6. 5 Hz, 1H), 8.28–8.20 (m, 4H), 7.99–7.78 (m, 5H), 7.73–7.68 (m,
1H), 7.58 (d, J=5.7 Hz, 1H), 7.32 (t, J=6.3 Hz, 1H), 7.22 (t, J=6.3 Hz,
1H), 6.99–6.83 (m, 3H), 6.77 (t, J=7.4 Hz, 1H), 6.22 (d, J=7.5 Hz, 1H),
6.16 (d, J=7.5 Hz, 1H), 3.96–3.89 (m, 1H), 3.78–3.62 (m, 2H), 3.09–
3.01 ppm (m, 1H); 13C NMR (75 MHz, [D6]DMSO): d=168.4, 167.3,
167.1, 152.9, 150.4, 150.1, 149.0, 147.7, 146.6, 144.5, 143.8, 139.4, 138.4,
138.2, 131.4, 131.1, 130.0, 129.9, 129.3, 125.7, 124.9, 124.5, 123.7, 121.8,
121.4, 119.6, 119.4, 51.6, 44.9 ppm (several signals in the aromatic region
overlapped); ATR-IR: n˜ =3409 (w), 1606 (w), 1583 (w), 1451 (w), 1418
(w), 1286 (w), 1267 (w), 1164 (w), 1033 (w), 832 (s), 756 (s), 736 (s), 668
(w), 630 (w), 555 (s), 416 cmÀ1 (w); HRMS (ESI): m/z calcd for
[C30H25IrN5]+: 646.1710; found: 646.1716 [M]+.
Synthesis of PS6:[25] Prepared by using method A (CH2Cl2, EtOH proce-
1
dure) to give PS6 as a yellow solid (99%). H NMR (300 MHz, CD2Cl2):
d=8.42 (d, J=8.0 Hz, 2H), 8.26 (d, J=5.7 Hz, 2H), 8.15 (t, J=7.9 Hz,
2H), 7.83 (t, J=7.8 Hz, 2H), 7.65 (d, J=8.2 Hz, 2H), 7.34 (d, J=7.7 Hz,
2H), 7.16 (t, J=6.6 Hz, 2H), 7.11 (d, J=7.8 Hz, 2H), 7.01 (t, J=6.3 Hz,
2H), 6.76 (t, J=7.8, 5.9 Hz, 4H), 6.60 (d, J=6.2 Hz, 4H), 6.55 (t, J=
6.1 Hz, 2H), 6.21 (t, J=6.2 Hz, 2H), 5.24 (d, J=7.8 Hz, 2H); ATR-IR:
n˜ =3043 (w), 1607 (w), 1583 (w), 1478 (w), 1450 (w), 1269 (w), 1227 (w),
1165 (w), 1064 (w), 1031 (w), 836 (s), 757 (m), 733 (m), 696 (w), 556 (m),
491 cmÀ1 (w).
Synthesis of PS7: Prepared by using method A to give PS7 as a yellow
powder (99%). 1H NMR (400 MHz, [D6]DMSO): d=8.79 (d, J=8.2 Hz,
1H), 8.41 (d, J=7.5 Hz, 1H), 8.30–8.14 (m, 4H), 7.96–7.84 (m, 4H), 7.81
(d, J=6.7 Hz, 1H), 7.73 (d, J=4.6 Hz, 1H), 7.60 (t, J=6.0 Hz, 1H), 7.48
(d, J=5.1 Hz, 1H), 7.20–7.13 (m, 2H), 7.09 (t, J=6.6 Hz, 1H), 6.98 (t,
J=7.5 Hz, 1H), 6.85 (t, J=7.5 Hz, 2H), 6.78 (t, J=7.3 Hz, 1H), 6.08–6.00
(m, 2H), 3.16 ppm (s, 3H); 13C NMR (100 MHz, [D6]DMSO): d=167.9,
166.4, 165.9, 156.2, 153.7, 152.2, 150.0, 149.4, 149.3, 148.3, 143.4, 143.0,
142.7, 139.3, 138.5, 138.4, 130.6, 130.3, 130.1, 128.9, 128.1, 125.2, 125.0,
124.1, 123.9, 123.1, 122.1, 120.4, 119.9, 119.5, 117.3, 110.0, 56.2 ppm;
ATR-IR: n˜ =3042 (w), 1606 (w), 1581 (w), 1473 (w), 1435 (w), 1288 (w),
1138 (w), 836 (s), 773 (w), 758 (m), 731 (m), 642 (w), 557 cmÀ1 (m);
HRMS (ESI): m/z calcd for [C33H26IrN4O]+: 685.1707; found: 685.1715
[M]+.
Synthesis of PS12: Prepared by using method B to give PS12 as a solid
(99%). 1H NMR (300 MHz, [D6]DMSO): d=8.29–8.23 (m, 5H), 8.04–
7.94 (m, 2H), 7.90–7.75 (m, 4H), 7.60 (d, 1H, JHH =7.3 Hz), 7.31 (t, 1H,
J
J
HH =6.9 Hz), 7.25 (t, 1H, JHH =6.2 Hz), 7.02–6.80 (m, 4H), 6.18 (d, 1H,
HH =7.5 Hz), 6.13 (d, 1H, JHH =7.5 Hz), 4.27–4.16 (m, 1H), 3.97–3.87 (m,
1H), 3.74–3.65 (m, 1H), 3.55–3.43 ppm (m, 1H); 13C NMR (75 MHz,
[D6]DMSO) d=176.5, 166.9, 166.7, 150.3, 150.3, 150.2, 150.0, 149.3, 147.1,
143.9, 143.9, 140.2, 138.8, 131.2, 130.9, 130.7, 130.0, 129.6, 128.8, 125.0,
124.7, 124.0, 124.0, 122.3, 122.0, 119.8, 119.7, 61.8, 33.8 ppm (several sig-
nals in the aromatic region overlapped); ATR-IR: n˜ =3044 (w), 1607 (w),
1582 (w), 1478 (w), 1420 (w), 1269 (w), 1247 (w), 1164 (w), 1054 (w),
1032 (w), 836 (s), 758 (m), 738 (m), 670 (w), 556 cmÀ1 (m); HRMS (ESI):
m/z: calcd for [C30H24IrN4S]+: 663.1222; found: 663.1324 [M]+.
Synthesis of PS8: Prepared by using method A (CH2Cl2, EtOH proce-
dure) to give PS8 as
a
brown solid (60%). 1H NMR (300 MHz,
7004
ꢄ 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Chem. Eur. J. 2011, 17, 6998 – 7006