Table 1.
Summary of (photo)physical properties of Het‐HTIs 1 to 16.
|
Compound |
Solvent |
Isomer yield in pss (at irr. λ in nm) |
Quantum yield Φ (Z→E, E→Z) |
Thermal isomerization ΔG ≠ in kcal mol−1 |
E isomer half lives linearly extrapol. to 25 °C |
Extinction λmax in nm (isomer, ϵ in L mol−1 cm−1) |
|---|---|---|---|---|---|---|
|
1 |
C6H6 |
100 % E (420), 100 % Z (515) |
|
27.7 |
82 d |
450 (Z, 13 000), 497 (E, 14 000) |
|
|
THF |
91 % E (430), 100 % Z (530) |
69 %, 43 % |
|
|
452 (Z, 32 900), 492 (E, 27 100) |
|
|
ACN |
93 % E (405), 100 % Z (530) |
43 %, 17 % |
24.2 |
12 h |
448 (Z, 17 400), 488 (E, 18 800) |
|
|
MeOH |
81 % E (450), 85 % Z (505) |
|
20.0 |
1 min |
|
|
2 |
DMSO |
– |
|
|
|
455 (Z, 27 800), 609 (Z, 900) |
|
3 |
toluene |
84 % E (405), 100 % Z (505) |
34 %, 17 % |
24.0 |
12 h |
427 (Z, 15 500), 450 (E, 10 600) |
|
|
DMSO |
76 % E (405), 97 % Z (505) |
|
21.0 |
5 min |
433 (Z, 23 400), 448 (E, 15 500) |
|
4 |
toluene |
100 % E (420), 94 % Z (505) |
|
30.5 |
35 years |
468 (Z, 12 400), 519 (E, 15 700) |
|
|
THF |
95 % E (450), 95 % Z (530) |
65 %, 41 % |
|
|
471 (Z, 41 000), 516 (E, 33 800) |
|
|
DMSO |
87 % E (420), 95 % Z (590) |
36 %, 43 % |
21.1 |
5 min |
481 (Z, 17 000), 521 (E, 19 100) |
|
5 |
THF |
89 % E (405), 92 % Z (530) |
35 %, 26 % |
20.4 |
1 min |
455 (Z, 41 900), 487 (E, 38 900) |
|
6 |
THF |
87 % E (405), 100 % Z (530) |
42 %, 54 % |
22.6 |
25 min |
452 (Z, 44 000), 483 (E, 44 000) |
|
7 |
THF |
85 % E (405), 100 % Z (530) |
39 %, 48 % |
22.4 |
25 min |
454 (Z, 44 500), 485 (E, 42 000) |
|
8 |
|
|
|
|
|
532 (E, 33 100) |
|
9 |
toluene |
95 % E (450), 88 % Z (530) |
53 % |
26.5 |
15 d |
445 (Z, 32 000), 475 (E, 23 900) |
|
|
DMSO |
80 % E (405), 46 % Z (505) |
|
21.1 |
5 min |
|
|
10 |
toluene |
|
|
|
|
461 (Z, 35 100), 482 (E, 31 800) |
|
|
ACN |
80 % E (405), 46 % Z (505) |
19 %, 8 % |
25.5 (DMSO) |
3 d |
456 (Z,40 000), 477 (E, 35 000) |
|
11 |
toluene |
|
|
24.3 (DMSO) |
12 h |
432 (Z, 17 200), 456 (E, 16 000) |
|
12 |
C6H6 |
decomposition |
|
|
|
|
|
|
DMSO |
decomposition |
|
|
|
434 (Z, 10 300) |
|
13 |
C6H6 |
decomposition |
|
|
|
|
|
|
DMSO |
decomposition |
|
|
|
433 (Z, 9 500) |
|
|
ACN |
70 % E (450) decomposition |
|
|
|
|
|
14 |
C6H6 |
decomposition |
|
|
|
|
|
|
DMSO |
decomposition |
|
|
|
451 (Z, 17 000) |
|
15 |
toluene |
decomposition |
|
|
|
|
|
|
DMSO |
decomposition |
|
|
|
459 (Z, 17 800) |
|
16 |
toluene |
decomposition |
|
|
|
|
|
|
DMSO |
decomposition |
|
|
|
446 (Z, 9 100) |