Table 1. Anodic and cathodic half-wave potentials values (mV) measured using CV for selected [4]helicenes (10−3 M) in acetonitrile ([TBA][PF6] 10−1 M) at a Pt electrode (Ø = 3 mm, ν = 0.1 V s−1), E vs. Fc/Fc+. Compounds are ranked by increasing first oxidation potentials. Redn and Oxn represent the n successive reduction and oxidation processes, respectively.
| Molecule | Functional group (Y) | Reductiona | Oxidationa | ||||
|---|---|---|---|---|---|---|---|
| Red1 | ΔE(Red1)b | Red2 | Ox1 | ΔE(Ox1)b | Ox2 | ||
| 5 | NO2 | −970 | −256 | −1778 | 1304c | 420 | — |
| 6 | CHO | −1059 | −167 | −1269 | 1131 | 247 | — |
| 17c | CO2Et | −1091 | −135 | — | 1084 | 200 | — |
| 17f | CONHPr | −1120 | −106 | −1877 | 1000 | 116 | — |
| 1 | H | −1226 | 0 | — | 884 | 0 | — |
| 9 | N3 | −1094 | −132 | −1834c | 769 | −115 | 1275c |
| 16 | CO2− | −1285 | 59 | — | 711c | −173 | 1006 |
| 15 | OMe | −1164 | −62 | — | 640 | −244 | 1258c |
| 7 | NH2 | −1201 | −25 | — | 354 | −530 | 781c |
| 8 | NMe2 | −1191 | −35 | — | 342 | −542 | 673 |
Half-wave potentials values, otherwise noted.
Potential difference compared to the first reduction or oxidation waves of compound 1.
Irreversible process.