| ¹H NMR (700 MHz, DMSO-d₆) | δ 8.34 (d, J = 8.4 Hz, 2H, H-7), 7.98 (dd, J = 8.5, 1.1 Hz, 2H, H-12), 7.94 (dd, J = 8.2, 1.4 Hz, 2H, H-9), 7.76 – 7.71 (m, 4H, H-6, H-11), 7.57 (ddd, J = 8.1, 6.8, 1.2 Hz, 2H, H-10), 4.03 (s, 4H, H-4), 3.43 (d, J = 2.4 Hz, 2H, H-3), 3.28 (t, J = 2.3 Hz, 1H, H-1) |
|---|---|
| ¹³C NMR (176 MHz, DMSO-d₆) | δ 159.49 (C-5), 146.99 (C-13), 136.55 (C-7), 129.49 (C-11), 128.59 (C-12), 127.79 (C-9), 127.04 (C-8), 126.23 (C-10), 120.95 (C-6), 78.68 (C-2), 76.38 (C-1), 59.50 (C-4), 42.31 (C-3) |
| HRMS (ESI+) | (C23H20N3)+ m/z (calculated) 338.1652, (found) 338.1661, mass difference 2.9 ppm |
| ATIR | ṽ (cm⁻¹) 3158, 3056, 1600, 1564, 1501, 1444, 1310, 952, 829, 815, 763 (s), 744 (s), 620, 475 |
| Experimental and calculated lifetime data (solid state) | t1 (Rel.%) 3.55 (22.5 %), t1 (Rel.%) 12.86 (75.1 %), t1 (Rel.%) 135.8 (2.4 %), tave (ns) 13.0 |
| Excitation (nm, solid state) | 360 |
| Emission (nm, solid state) | 444 |
| Stokes shift (cm⁻¹, solid state) | 5300 |
David R. Husbands, Gustavo Clauss, Lukas Geciauskas, Robin E. Kroon, Mmabatho L. Ledibane, Orbett Alexander, Angelo Frei. “Synthesis, physical, chemical and biological properties of a M(CO)3 (M = Cr, Mo, W, Mn, Re) matched quintet.” ChemRxiv (). https://doi.org/10.26434/chemrxiv.15007450/v1
| ¹H NMR (700 MHz, DMSO-d₆) | δ 9.23 (d, J = 8.7 Hz, 2H, H-12), 8.30 (d, J = 8.4 Hz, 2H, H-7), 7.93 (d, J = 8.0 Hz, 2H, H-9), 7.78 (t, J = 7.8 Hz, 2H, H-11), 7.59 (t, J = 7.6 Hz, 2H, H-10), 7.46 (d, J = 8.4 Hz, 2H, H-6), 4.74 (d, J = 17.1 Hz, 2H, H-4), 4.44 (s, 2H, H-3), 4.40 (d, J = 17.1 Hz, 2H, H-4), 3.63 (d, J = 2.4 Hz, 1H, H-1) |
|---|---|
| ¹³C NMR (176 MHz, DMSO-d₆) | δ 234.01 (C≡O), 231.91 (C≡O), 161.95 (C-5), 147.76 (C-13), 137.78 (C-7), 130.44 (C-11), 129.30 (C-12), 128.55 (C-9), 127.67 (C-8), 126.78 (C-10), 119.05 (C-6), 78.06 (C-1), 77.50 (C-2), 65.54 (C-4), 52.98 (C-3) |
| HRMS (LIFDI) | (C₂₆H₁₉N₃O₃Cr)⁺˙ m/z (calculated) 473.08260, (found) 473.08167, mass difference 1.97 ppm |
| ATIR | ṽ (cm⁻¹) 1886 (vs, C≡O), 1754 (vs, C≡O) |
| λmax (UV-vis, DMSO) / nm | 485.8, 368, 295.8 |
| Emission λmax (DMSO) / nm | 440 |
| Experimental and calculated lifetime data (solid state) | t1 (Rel.%) 4.03 (23.6 %), t1 (Rel.%) 12.82 (74.2 %), t1 (Rel.%) 131.9 (2.2 %), tave (ns) 13.3 |
| Excitation (nm, solid state) | 358 |
| Emission (nm, solid state) | 440 |
| Stokes shift (cm⁻¹, solid state) | 5200 |
| ¹H NMR (700 MHz, DMSO-d₆) | δ 9.08 (dd, J = 8.7, 1.1 Hz, 2H, H-12), 8.32 – 8.28 (m, 2H, H-7), 7.86 (dd, J = 8.1, 1.5 Hz, 2H, H-9), 7.77 (ddd, J = 8.6, 6.9, 1.5 Hz, 2H, H-11), 7.54 (ddd, J = 8.0, 6.9, 1.1 Hz, 2H, H-10), 7.51 (d, J = 8.5 Hz, 2H, H-6), 4.73 (d, J = 16.6 Hz, 2H, H-4), 4.54 (d, J = 16.7 Hz, 2H, H-4), 4.39 (d, J = 2.4 Hz, 2H, H-3), 3.65 (t, J = 2.4 Hz, 1H, H-1) |
|---|---|
| ¹³C NMR (176 MHz, DMSO-d₆) | δ 228.80 (C≡O), 228.25 (C≡O), 161.59 (C-5), 146.89 (C-13), 138.23 (C-7), 130.56 (C-11), 129.87 (C-12), 128.25 (C-9), 127.19 (C-10), 127.00 (C-8), 119.99 (C-6), 78.54 (C-1), 77.17 (C-2), 65.52 (C-4), 53.67 (C-3) |
| HRMS (LIFDI) | (C₂₆H₁₉N₃O₃Mo)⁺˙ m/z (calculated) 519.04750, (found) 519.04952, mass difference 3.88 ppm |
| ATIR | ṽ (cm⁻¹) 1888 (vs, C≡O), 1748 (vs, br, C≡O) |
| λmax (UV-vis, DMSO) / nm | 457, 298 |
| Emission λmax (DMSO) / nm | 442 |
| Experimental and calculated lifetime data (solid state) | t1 (Rel.%) 3.37 (21.3 %), t1 (Rel.%) 12.84 (76.5 %), t1 (Rel.%) 147.6 (2.2 %), tave (ns) 13.8 |
| Excitation (nm, solid state) | 360 |
| Emission (nm, solid state) | 442 |
| Stokes shift (cm⁻¹, solid state) | 5200 |
| ¹H NMR (700 MHz, DMSO) | δ 9.10 (dd, J = 8.6, 1.0 Hz, 2H, H-12), 8.35 – 8.32 (m, 2H, H-7), 7.87 (dd, J = 8.0, 1.5 Hz, 2H, H-9), 7.75 (ddd, J = 8.7, 6.9, 1.6 Hz, 2H, H-11), 7.55 – 7.53 (m, 4H, H-10, H-6), 4.81 – 4.74 (m, 4H, H-4), 4.47 (d, J = 2.4 Hz, 2H, H-3), 3.71 (t, J = 2.4 Hz, 1H, H-1) |
|---|---|
| ¹³C NMR (176 MHz, DMSO) | δ 224.37 (C≡O), 223.14 (C≡O), 162.66 (C-5), 146.79 (C-13), 138.25 (C-7), 130.80 (C-11), 130.62 (C-12), 128.36 (C-9), 127.25 (C-8), 127.17 (C-10), 119.98 (C-6), 78.86 (C-1), 77.51 (C-2), 66.74 (C-4), 55.16 (C-3) |
| HRMS (LIFDI) | (C₂₆H₁₉N₃O₃W)⁺˙ m/z (calculated) 605.09303, (found) 605.09267, mass difference 0.59 ppm |
| ATIR | ṽ (cm⁻¹) 1879 (vs, C≡O), 1743 (vs, C≡O) |
| λmax (UV-vis, DMSO) / nm | 478.2, 315.6, 302.6, 296.6 |
| Emission λmax (DMSO) / nm | 434 |
| Experimental and calculated lifetime data (solid state) | t1 (Rel.%) 3.66 (27.1 %), t1 (Rel.%) 12.88 (70.8 %), t1 (Rel.%) 129.13 (2.1 %), tave (ns) 12.8 |
| Excitation (nm, solid state) | 341 |
| Emission (nm, solid state) | 434 |
| Stokes shift (cm⁻¹, solid state) | 6300 |
| ¹H NMR (700 MHz, DMSO) | δ 8.62 (d, J = 8.4 Hz, 2H, H-7), 8.35 (d, J = 8.7 Hz, 2H, H-12), 8.16 (dd, J = 8.2, 1.5 Hz, 2H, H-9), 7.92 (ddd, J = 8.7, 7.0, 1.5 Hz, 2H, H-11), 7.75 (t, J = 7.5 Hz, 2H, H-10), 7.67 (d, J = 8.4 Hz, 2H, H-6), 5.11 (d, J = 18.2 Hz, 2H, H-4), 4.80 (d, J = 18.2 Hz, 2H, H-4), 4.71 (d, J = 2.4 Hz, 2H, H-3), 3.91 (d, J = 2.3 Hz, 1H, H-1) |
|---|---|
| ¹³C NMR (176 MHz, DMSO) | δ 219.65 (C≡O), 218.41 (C≡O), 164.71 (C-5), 147.04 (C-13), 140.51 (C-7), 132.29 (C-11), 129.95 (C-9), 128.55 (C-8), 127.70 (C-10), 126.05 (C-12), 119.72 (C-6), 80.76 (C-1), 77.80 (C-2), 68.39 (C-4), 53.92 (C-3) |
| ¹⁹F NMR (659 MHz, DMSO) | δ -77.74 (s) |
| HRMS (ESI+) | (C26H19MnN3O3)+ m/z (calculated) 476.0801, (found) 476.0795, mass difference 1.9 ppm |
| LCMS retention time (ESI+, 7 min method, H2O:MeCN 0.1 % formic acid) | 2.57 min, m/z 313.11 |
| ATIR | ṽ (cm⁻¹) 2030 (vs, C≡O), 1941 (vs, C≡O), 1923 (vs, C≡O) |
| λmax (UV-vis, DMSO) / nm | 361.8, 321.2, 310 |
| Emission λmax (DMSO) / nm | 436 |
| Fluorescence quantum yield (solid state) | 11 % |
| Experimental and calculated lifetime data (solid state) | t1 (Rel.%) 3.13 (48.9 %), t1 (Rel.%) 12.97 (48.6 %), t1 (Rel.%) 137.0 (2.5 %), tave (ns) 11.3 |
| Excitation (nm, solid state) | 355 |
| Emission (nm, solid state) | 436 |
| Stokes shift (cm⁻¹, solid state) | 5200 |
| ¹H NMR (700 MHz, DMSO-d₆) | δ 8.71 (d, J = 8.4 Hz, 2H, H-7), 8.39 (d, J = 8.8 Hz, 2H, H-12), 8.16 (dd, J = 8.2, 1.5 Hz, 2H, H-9), 7.98 (ddd, J = 8.7, 7.0, 1.6 Hz, 2H, H-11), 7.79 – 7.74 (m, 4H, H-6, H-10), 5.23 (d, J = 18.0 Hz, 2H, H-4), 5.17 (d, J = 18.0 Hz, 2H, H-4), 4.77 (d, J = 2.5 Hz, 2H, H-3), 3.89 (t, J = 2.4 Hz, 1H, H-1) |
|---|---|
| ¹³C NMR (176 MHz, DMSO-d₆) | δ 196.21 (C≡O), 193.96 (C≡O), 165.55 (C-5), 146.06 (C-13), 141.40 (C-7), 132.96 (C-11), 129.86 (C-9), 128.10 (C-10), 127.59 (C-12), 120.37 (C-6), 80.99 (C-1), 77.82 (C-2), 68.84 (C-4), 55.56 (C-3) |
| ¹⁹F NMR (659 MHz, DMSO-d₆) | δ -77.75 |
| HRMS (ESI+) | (C26H19N3O3Re)+ m/z (calculated) 608.0978, (found) 608.0963, mass difference 2.3 ppm |
| LCMS retention time (ESI+, 7 min method, H2O:MeCN 0.1 % formic acid) | 2.57 min, m/z 313.11 |
| ATIR | ṽ (cm⁻¹) 2028 (vs, C≡O), 1925 (vs, C≡O), 1907 (vs, C≡O) |
| λmax (UV-vis, DMSO) / nm | 322, 315.8 |
| Emission λmax (DMSO) / nm | 436 |
| Fluorescence quantum yield (solid state) | 2.3 % |
| Experimental and calculated lifetime data (solid state) | t1 (Rel.%) 3.03 (48.7 %), t1 (Rel.%) 12.84 (48.8 %), t1 (Rel.%) 119.8 (2.5 %), tave (ns) 10.7 |
| Excitation (nm, solid state) | 363 |
| Emission (nm, solid state) | 436 |
| Stokes shift (cm⁻¹, solid state) | 4600 |
| HRMS (ESI+) | (C33H26MnN6O3)+ m/z (calculated) 609.1441, (found) 609.1444, mass difference 1.8 ppm |
|---|---|
| LCMS retention time (ESI+, 7 min method, H2O:MeCN 0.1 % formic acid) | 3.98 min, m/z 609.08 (major isomer); 3.70 min, m/z 609.07 (minor isomer) |
| ATIR | ṽ (cm⁻¹) 2032 (vs, C≡O), 1919 (vs, C≡O) |
| IR spectrum of the solid product | carbonyl bands at 2028 and 1925 cm⁻¹ |