Table 1. Photophysical Properties of Nucleosides 1a–fa.
|
|
Stokes
shift |
|||||||
---|---|---|---|---|---|---|---|---|---|
substituent | absorption |
emission |
brightness | νabs –
νem |
|||||
compound | Y | solvent | λmax [nm] | εb | λmax [nm] | Φc | Φ × ε × 103 | [cm–1] | [kcal/mol] |
B(22) | (R = ribose) (X = S) | dioxane | 335 | 13 | 415 | 0.80 | 10.4 | 6025 | 16.4 |
methanol | 334 | 11 | 433 | 0.50 | 5.5 | 7332 | 19.6 | ||
water | 332 | 11 | 455 | 0.20 | 2.2 | 8492 | 23.3 | ||
1a | F | dioxane | 368 | 15.0 | 462 | 0.32 | 4.8 | 5504 | 15.7 |
methanol | 365 | 14.0 | 488 | 0.11 | 1.5 | 6867 | 19.6 | ||
water | 357 | 12.6 | 478 | 0.24 | 3.0 | 7140 | 20.4 | ||
1b | H | dioxane | 371 | 9.7 | 461 | 0.30 | 2.9 | 5286 | 15.1 |
methanol | 367 | 8.9 | 488 | 0.16 | 1.4 | 6767 | 19.3 | ||
water | 356 | 9.6 | 478 | 0.21 | 2.0 | 7184 | 20.5 | ||
1c | Me | dioxane | 375 | 14.6 | 468 | 0.38 | 5.6 | 5308 | 15.2 |
methanol | 372 | 14.0 | 499 | 0.07 | 1.0 | 6855 | 19.6 | ||
water | 360 | 13.9 | 490 | 0.12 | 1.7 | 7370 | 21.1 | ||
1d | MeO | dioxane | 383 | 20.8 | 486 | 0.74 | 15.4 | 5534 | 15.8 |
water | 366 | 19.7 | 525 | 0.02 | 0.4 | 8275 | 23.7 | ||
1e | HO | dioxane | 385 | 16.9 | 494 | 0.71 | 12.0 | 5695 | 16.3 |
water | 381 | 15.0 | 517 | <0.01 | <0.1 | 6944 | 19.8 | ||
1f | Me2N | dioxane | 420 | 21.4 | 575 | 0.20 | 4.3 | 6428 | 18.4 |
water | 398 | 16.8 | 484 | <0.01 | <0.1 | 4464 | 12.8 |
Absorption and steady-state emission spectroscopy studies were performed using samples prepared from a concentrated DMSO stock solution.25
ε in [× 103 M–1 cm–1].
Fluorescence standards: Coumarin 102 was used for 1a–e, and Coumarin 153 was used for 1f.