Table 1:
Computed emission wavelengths (λem, in nm) and oscillator strengths (f) of oxyluciferin and its analogs in aqueous solution at TD-ωB97X-D/6–311++G**/C-PCM level of theory. Substituent groups are ordered according to the wavelengths of the C7’-OLU analogs. Δλem is the difference between the computed emission wavelengths of the unsubstituted oxyluciferin and a substituted OLU analog.
| Group | site C7’ | site C5’ | site C4’ | ||||||
|---|---|---|---|---|---|---|---|---|---|
| λ em | Δλem | f | λ em | Δλem | f | λ em | Δλem | f | |
| NO2 | 490.5 | −88.6 | 1.232 | 583.7 | 4.6 | 1.009 | 654.0 | 74.9 | 0.635 |
| CN | 517.7 | −61.4 | 1.279 | 564.6 | −14.5 | 1.204 | 587.4 | 8.3 | 1.164 |
| COCH3 | 519.5 | −59.6 | 1.288 | 589.7 | 10.6 | 1.165 | 598.2 | 19.1 | 1.158 |
| CF3 | 528.3 | −50.8 | 1.304 | 560.7 | −18.4 | 1.186 | 575.0 | −4.1 | 1.218 |
| I | 559.0 | −20.1 | 1.269 | 571.7 | −7.4 | 1.342 | 581.9 | 2.8 | 1.186 |
| CCH | 561.0 | −18.1 | 1.236 | 580.6 | 1.5 | 1.337 | 589.5 | 10.4 | 1.181 |
| Br | 561.1 | −18.0 | 1.267 | 569.6 | −9.5 | 1.325 | 579.0 | −0.1 | 1.191 |
| Cl | 563.7 | −15.4 | 1.266 | 568.0 | −11.1 | 1.303 | 577.9 | −1.2 | 1.192 |
| H | 579.1 | 0.0 | 1.270 | 579.1 | 0.0 | 1.270 | 579.1 | 0.0 | 1.270 |
| F | 584.2 | 5.1 | 1.230 | 563.2 | −15.9 | 1.297 | 571.2 | −7.9 | 1.200 |
| CHCH2 | 592.1 | 13.0 | 1.232 | 597.5 | 18.4 | 1.349 | 599.8 | 20.7 | 1.107 |
| OH-2 | 662.7 | 83.6 | 1.089 | 586.0 | 6.9 | 1.388 | 584.2 | 5.1 | 1.164 |
| OH | 665.8 | 86.7 | 1.007 | 574.1 | −5.0 | 1.383 | 579.7 | 0.6 | 1.174 |
| NH2 | 825.8 | 246.7 | 0.793 | 640.9 | 61.8 | 1.402 | 605.7 | 26.6 | 1.031 |
| N(CH3)2 | 882.0 | 302.9 | 0.719 | 645.3 | 66.2 | 1.428 | 608.4 | 29.3 | 1.048 |
| NCH3H | 888.5 | 309.4 | 0.741 | 651.6 | 72.5 | 1.384 | 596.4 | 17.3 | 0.993 |
| NHCH3 | 925.8 | 346.7 | 0.658 | 689.5 | 110.4 | 1.367 | 614.6 | 35.5 | 1.031 |