X. Wei, et al.
JournalofInorganicBiochemistry202(2020)110857
Bipy-H6′), 8.58 (d, J = 8.4 Hz, 1H, Bipy-H3), 8.51 (d, J = 4.8 Hz, 1H,
Bipy-H3′), 8.44 (td, J1 = 7.8 Hz, J2 = 1.2 Hz, 1H, Bipy-H4), 8.41 (td,
J1 = 7.8 Hz, J2 = 1.2 Hz, 1H, Bipy-H4′), 7.95 (t, J = 6.6 Hz, 1H, Bipy-
H5), 7.86 (t, J = 6.6 Hz, 1H, Bipy-H5′), 7.63 (d, J = 15.6 Hz, 1H, H6),
7.33 (d, J = 1.8 Hz, 1H, AreH2), 7.31 (dd, J1 = 7.8 Hz, J2 = 1.8 Hz,
1H, AreH6), 7.01 (d, J = 8.4 Hz, 1H, AreH5), 6.85 (d, J = 15.6 Hz, 1H,
H5), 5.91 (s, 1H, H3), 3.83 (s, 3H, OCH3-3), 3.82 (s, 3H, OCH3-4), 2.26
(s, 3H, CH3). 13C NMR (DMSO-d6, 150 MHz) δ: 187.90(C-2), 177.
C5),
127.57(Bipy-C5′),
124.03(Bipy-C3),
123.77(Bipy-C3′),
119.49(AreC6), 117.54(AreC2), 114.76(AreC4), 103.85(C-3),
25.97(C-1). ESI-MS (m/z): [M-PF6]+ calcd for C22H19N2O3Pd, 465.0;
Found: 465.0. Anal. calcd for C22H19F6N2O3PPd: C, 43.26; H, 3.14; N,
4.59. Found: C, 43.37; H, 3.27; N, 4.64%.
2.2.2.8. Complex 3h. Yellow solid, Yield: 86%. 1H NMR (600 MHz,
DMSO-d6) δ: 10.13 (br s, 1H, Ar-OH), 8.49–8.50 (m, 3H, Bipy-H6, Bipy-
H6′ and Bipy-H3), 8.38 (d, J = 5.4 Hz, 1H, Bipy-H3′), 8.32–8.36 (m,
2H, Bipy-H4 and Bipy-H4′), 7.86 (t, J = 6.6 Hz, 1H, Bipy-H5), 7.80 (t,
J = 6.6 Hz, 1H, Bipy-H5′), 7.57 (d, J = 8.4 Hz, 2H, AreH2 and AreH6),
7.48 (d, J = 15.6 Hz, 1H, H6), 6.84 (d, J = 8.4 Hz, 2H, AreH3 and
AreH5), 6.59 (d, J = 15.6 Hz, 1H, H5), 5.74 (s, 1H, H3), 2.16 (s, 3H,
CH3). 13C NMR (DMSO‑d6, 150 MHz) δ: 187.25(C-2), 177.29(C-4),
159.88(AreC4), 155.20(Bipy-C2), 155.17(Bipy-C2′), 146.65(Bipy-C6),
146.48(Bipy-C6′), 141.86(Bipy-C4 and Bipy-C4′), 141.54(C-6),
130.48(AreC2 and AreC6), 127.80(Bipy-C5), 127.46(Bipy-C5′),
125.63(C-5), 123.87(Bipy-C3), 123.84(Bipy-C3′), 120.08(AreC1),
115.84(AreC3 and AreC5), 103.39(C-3), 25.69(C-1). ESI-MS (m/z):
[M-PF6]+ calcd for C22H19N2O3Pd, 465.0; Found: 465.0. Anal. calcd for
84(C-4),
155.73(Bipy-C2),
141.71(C-6),
155.68(Bipy-C2′),
127.92(Bipy-C5),
151.14(AreC3),
127.56(Bipy-C5′),
149.00(AreC4), 146.86(Bipy-C6 and Bipy-C6′), 142.10(Bipy-C4 and
Bipy-C4′),
124.04(Bipy-C3), 124.02(Bipy-C3′), 123.53(AreC1), 121.76 (AreC6),
111.54(AreC5), 110.18(AreC2), 103.62(C-3), 55.60(OCH3-3 and
OCH3-4), 25.91(C-1). ESI-MS (m/z): [M-PF6]+ calcd for
C
C
24H23N2O4Pd,
509.1;
Found:
509.1.
Anal.
calcd
for
24H23F6N2O4PPd: C, 44.02; H, 3.54; N, 4.28. Found: C, 44.27; H,
3.32; N, 4.39%.
2.2.2.5. Complex 3e. Yellow solid, Yield: 95%. 1H NMR (600 MHz,
DMSO-d6) δ: 8.60 (d, J = 4.8 Hz, 1H, Bipy-H6), 8.58 (d, J = 4.8 Hz, 1H,
Bipy-H6′), 8.57 (d, J = 4.8 Hz, 1H, Bipy-H3), 8.47 (d, J = 4.8 Hz, 1H,
Bipy-H3′), 8.42 (t, J = 7.8 Hz, 1H, Bipy-H4), 8.39 (t, J = 7.8 Hz, 1H,
Bipy-H4′), 7.92 (t, J = 6.6 Hz, 1H, Bipy-H5), 7.85 (t, J = 6.6 Hz, 1H,
Bipy-H5′), 7.55 (d, J = 15.6 Hz, 1H, H6), 6.93 (d, J = 15.6 Hz, 1H, H5),
6.88 (s, 2H, AreH2 and AreH6), 6.53 (s, 1H, AreH4), 5.92 (s, 1H, H3),
3.78 (s, 6H, OCH3–3 and OCH3–5), 2.26 (s, 3H, CH3). 13C NMR (DMSO-
d6, 150 MHz) δ: 188.83(C-2), 177.17(C-4), 160.66 (AreC3 an AreC5),
155.63(Bipy-C2), 155.58(Bipy-C2′), 147.21(Bipy-C6), 146.77(Bipy-
C6′), 142.05(Bipy-C4 and Bipy-C4′), 141.07(C-6), 136.59 (AreC1),
127.89(Bipy-C5), 127.52(Bipy-C5′), 124.68(C-5), 123.99(Bipy-C3 and
Bipy-C3′), 106.36 (AreC2 and AreC6), 104.04(C-3), 102.09 (AreC4),
55.32(OCH3-3 and OCH3-5), 26.02(C-1). ESI-MS (m/z): [M-PF6]+ calcd
for C24H23N2O4Pd, 509.1; Found: 509.1. Anal. calcd for
C
22H19F6N2O3PPd: C, 43.26; H, 3.14; N, 4.59. Found: C, 43.31; H, 3.26;
N, 4.61%.
2.2.2.9. Complex 3i. Yellow solid, Yield: 98%. 1H NMR (600 MHz,
DMSO‑d6) δ: 9.84 (br s, 1H, Ar-OH-3), 9.21 (br s, 1H, Ar-OH-4), 8.49 (d,
J = 8.4 Hz, 1H, Bipy-H6), 8.47 (d, J = 7.8 Hz, 2H, Bipy-H6′ and Bipy-
H3), 8.39 (d, J = 4.8 Hz, 1H, Bipy-H3′), 8.34 (t, J = 7.8 Hz, 1H, Bipy-
H4), 8.32 (t, J = 8.4 Hz, 1H, Bipy-H4′), 7.86 (t, J = 6.6 Hz, 1H, Bipy-
H5), 7.79 (t, J = 6.6 Hz, 1H, Bipy-H5′), 7.41 (d, J = 15.6 Hz, 1H, H6),
7.11 (s, 1H, AreH2), 7.05 (d, J = 7.8 Hz, 1H, AreH6), 6.80 (d,
J = 7.8 Hz, 1H, AreH5), 6.50 (d, J = 15.6 Hz, 1H, H5), 5.75 (s, 1H,
H3), 2.15 (s, 3H, CH3). 13C NMR (DMSO‑d6, 150 MHz) δ: 187.08(C-2),
177.34(C-4), 155.30(Bipy-C2), 155.26(Bipy-C2′), 148.58(AreC4),
146.70(Bipy-C6), 146.46(Bipy-C6′), 145.60(AreC3), 142.06(Bipy-C4),
142.05(Bipy-C4′), 141.83(C-6), 127.76(Bipy-C5), 127.44(Bipy-C5′),
126.19(AreC1), 123.89(C-5), 122.08(AreC6), 120.05(Bipy-C3),
120.02(Bipy-C3′), 115.66(AreC5), 114.75(AreC2), 103.31(C-3),
25.70(C-1). ESI-MS (m/z): [M-PF6]+ calcd for C22H19N2O3Pd, 481.0;
Found: 481.0. Anal. calcd for C22H19F6N2O4PPd: C, 42.16; H, 3.06; N,
4.47. Found: C, 42.19; H, 3.11; N, 4.46%.
C
24H23F6N2O4PPd: C, 44.02; H, 3.54; N, 4.28. Found: C, 43.85; H,
3.62; N, 4.30%.
2.2.2.6. Complex 3f. Yellow solid, Yield: 83%. 1H NMR (600 MHz,
DMSO‑d6) δ: 8.67 (d, J = 5.4 Hz, 1H, Bipy-H6), 8.60 (d, J = 9.0 Hz, 1H,
Bipy-H6′), 8.58 (d, J = 9.0 Hz, 1H, Bipy-H3), 8.52 (d, J = 5.4 Hz, 1H,
Bipy-H3′), 8.44 (t, J = 8.4 Hz, 1H, Bipy-H4), 8.41 (t, J = 8.4 Hz, 1H,
Bipy-H4′), 7.96 (t, J = 6.6 Hz, 1H, Bipy-H5), 7.87 (t, J = 6.6 Hz, 1H,
Bipy-H5′), 7.62 (d, J = 15.6 Hz, 1H, H6), 7.07 (s, 2H, AreH2 and
AreH6), 6.94 (d, J = 15.6 Hz, 1H, H5), 5.94 (s, 1H, H3), 3.85 (s, 6H,
OCH3-3 and OCH3-5), 3.73 (s, 3H, OCH3-4), 2.28 (s, 3H, CH3). 13C NMR
(DMSO-d6, 150 MHz) δ: 188.44(C-2), 177.55(C-4), 155.72(Bipy-C2),
155.67(Bipy-C2′), 153.08(AreC3 and AreC5), 147.31(Bipy-C6),
146.86(Bipy-C6′), 142.11(Bipy-C4), 141.45(Bipy-C4′), 139.61(C-6),
130.30(AreC4), 127.97(Bipy-C5), 127.56(Bipy-C5′), 124.06(Bipy-C3),
124.03(Bipy-C3′), 123.57(C-5), 106.04 (AreC2 and AreC6), 103.89(C-
3), 60.14(OCH3-4), 56.06(OCH3-3 and OCH3-5), 25.98(C-1). ESI-MS
(m/z): [M-PF6]+ calcd for C25H25N2O5Pd, 539.1; Found: 539.1. Anal.
calcd for C25H25F6N2O5PPd: C, 43.84; H, 3.68; N, 4.09. Found: C, 43.81;
H, 3.72; N, 4.11%.
2.2.2.10. Complex 3j. Yellow solid, Yield: 89%. 1H NMR (600 MHz,
DMSO‑d6) δ: 9.46 (s, 2H, Ar-OH-3 and Ar-OH-5), 8.65 (d, J = 5.4 Hz,
1H, Bipy-H6), 8.61 (d, J = 8.4 Hz, 2H, Bipy-H6′ and Bipy-H3), 8.54 (d,
J = 6.0 Hz, 1H, Bipy-H3′), 8.45–8.41 (m, 2H, Bipy-H4 and Bipy-H4′),
7.93 (t, J = 6.0 Hz, 1H, Bipy-H5), 7.88 (t, J = 6.0 Hz, 1H, Bipy-H5′),
7.54 (d, J = 15.6 Hz, 1H, H6), 6.75 (d, J = 15.6 Hz, 1H, H5), 6.62 (d,
J = 1.8 Hz, 2H, AreH2 and AreH6), 6.36 (t, J = 1.8 Hz, 1H, AreH4),
6.00 (s, 1H, H3), 2.27 (s, 3H, CH3). 13C NMR (DMSO-d6, 150MHz) δ:
188.51(C-2), 177.27(C-4), 158.65(AreC3 and AreC5), 155.58(Bipy-
C2),
155.54(Bipy-C2′),
147.12(Bipy-C6),
146.74(Bipy-C6′),
142.03(Bipy-C4 and Bipy-C4′), 141.87(C-6), 136.40(AreC1),
127.87(Bipy-C5), 127.55(Bipy-C5′), 124.04(Bipy-C3 and Bipy-C3′),
123.60(C-5), 106.55(AreC2 and AreC6), 104.90(AreC4), 103.73(C-
3), 25.96(C-1). ESI-MS (m/z): [M-PF6]+ calcd for C22H19N2O3Pd,
481.0; Found: 481.0. Anal. calcd for C22H19F6N2O4PPd: C, 42.16; H,
3.06; N, 4.47. Found: C, 42.19; H, 3.00; N, 4.49%.
2.2.2.7. Complex 3 g. Yellow solid, Yield: 86%. 1H NMR (600 MHz,
DMSO-d6) δ: 9.66 (s, 1H, Ar-OH), 8.62 (d, J = 4.8 Hz, 1H, Bipy-H6),
8.57 (d, J = 7.8 Hz, 2H, Bipy-H6′ and Bipy-H3), 8.49 (d, J = 4.8 Hz,
1H, Bipy-H3′), 8.42 (t, J = 8.4 Hz, 1H, Bipy-H4), 8.40 (t, J = 8.4 Hz,
1H, Bipy-H4′), 7.91 (t, J = 6.6 Hz, 1H, Bipy-H5), 7.86 (t, J = 6.6 Hz,
1H, Bipy-H5′), 7.59 (d, J = 15.6 Hz, 1H, H6), 7.26 (t, J = 7.8 Hz, 1H,
AreH5), 7.19 (d, J = 7.8 Hz, 1H, AreH6), 7.13 (s, 1H, AreH2), 6.87
(dd, J1 = 7.8 Hz, J2 = 1.2 Hz, 1H, AreH4), 6.82 (d, J = 15.6 Hz, 1H,
H5), 5.95 (s, 1H, H3), 2.25 (s, 3H, CH3). 13C NMR (DMSO-d6, 150 MHz)
δ: 188.54(C-2), 177.05(C-4), 157.71(AreC3), 155.46(Bipy-C2),
155.43(Bipy-C2′), 147.01(Bipy-C6), 146.65(Bipy-C6′), 142.03(Bipy-
C4), 141.38(Bipy-C4′), 135.95(AreC1), 129.84(AreC5), 127.89(Bipy-
2.2.2.11. Complex 3k. Yellow solid, Yield: 85%. 1H NMR (600 MHz,
DMSO‑d6) δ: 9.79 (br s, 1H, Ar-OH-4), 8.46(d, J = 5.4 Hz, 1H, Bipy-
H6), 8.44 (d, J = 7.8 Hz, 1H, Bipy-H6′), 8.43 (d, J = 7.8 Hz, 1H, Bipy-
H3), 8.34(d, J = 4.8 Hz, 1H, Bipy-H3′), 8.33(t, J = 7.8 Hz, 1H, Bipy-
H4), 8.29 (t, J = 7.8 Hz, 1H, Bipy-H4′), 7.86 (t, J = 6.0 Hz, 1H, Bipy-
H5), 7.76 (t, J = 6.0 Hz, 1H, Bipy-H5′), 7.41 (d, J = 15.6 Hz, 1H, H6),
7.23 (s, 1H, AreH2), 7.13 (d, J = 8.4 Hz, 1H, AreH6), 6.80 (d,
J = 8.4 Hz, 1H, AreH5), 6.61 (d, J = 15.6 Hz, 1H, H5), 5.70 (s, 1H,
4