Table 1 Quantitative comparison of the physical and photophysical properties of HIs 1-4
diary-HI | ΔG‡E→Z/ ΔG‡Z→E (kcal mol−1) | ΔG (kcal mol−1) | E:Z at thermal equilibrium (temperature) | equil. t1/2 at 25 °Cd | isomer % in pss (LED wavelength) | λmax (nm) and εmax (L mol−1 cm−1) of E/Z isomers lowest energy absorption band | Δλmax (nm) and Δεmax (L mol−1 cm−1) of E/Z isomers |
|---|---|---|---|---|---|---|---|
1a | 25.0a/25.3a | 0.3a | 39:61a (60 °C) | 1.5 daysa | 47% E (590 nm)a 94% Z (450 nm)a | 477c; 15,300c/ 518c; 12,200c | 41c; 3100c |
1b | 31.2b/31.4b | 0.3b | 42:58b (135 °C) | 118 yearsb | 62% E (625 nm)a 100% Z (470 nm)a | 499c; 7700c/ 539c; 7700c | 40c; 0c |
1c | 31.4b/31.9b | 0.5b | 34:66b (135 °C) | 199 yearsb | 63% E (625 nm)a 100% Z (470 nm)a | 493c; 9600c/ 534c; 7600c | 41c; 2000c |
2a | -e | -e | - e | -e | -e | -e | -e |
2b | 22.9a/22.5a | 0.4a | 67:33a (25 °C) | 36 mina | 79% E (625 nm)a 92% Z (490 nm)a | 518c; 9600c/ 563c; 8300c | 45c; 1300c |
2c | 29.2a /27.9a | 1.3a | 87:13a (80 °C) | 291 daysa | 92% E (660 nm)a 91% E (625 nm)g 92% Z (470 nm)a 81% Z (470 nm)g | 507c; 6000c/ 562c; 5100c | 55c; 900c |
3a | -b, f | 0.1b, f | 47:53b (0 °C) | -b, f | 50% E (530 nm)a 53% Z (450 nm)a | 477c; 5900c/ 523c; 4700c | 46c; 1200c |
3b | 27.4a/27.5a | 0.1a | 46:55a (80 °C) | 74 daysa | 62% E (590 nm)a 92% Z (470 nm)a | 512c; 9700c/ 542c; 9000c | 30c; 700c |
3c | 24.5a/24.6a | 0.1a | 48:52a (60 °C) | 14 ha | 46% E (550 nm)a 72% Z (470 nm)a | 503c; 8800c/ 541c;7300c | 38c; 1500c |
4a | -a, e | -a, e | -a, e | -a, e | -a, e | -c, e | -c, e |
4b | 26.5a/27.4a | 0.8a | 23:77a (80 °C) | 27 daysa | 89% E (505 nm)a 81% E (505 nm)g 87% Z (660 nm)a 88% Z (625 nm)g | 561c; 6500c/ 517c; 7100c | 44c; 600c |
4c | 26.8a/27.5a | 0.7a | 26:74a (80 °C) | 40 daysa | 90% E (490 nm)a 90% E (490 nm)g 93% Z (660 nm)a 88% Z (625 nm)g | 560c; 3600c/ 507c; 4100c | 53c; 500c |