Table 1 Quantitative comparison of the physical and photophysical properties of HIs 1-4

From: Diaryl-hemiindigos as visible light, pH, and heat responsive four-state switches and application in photochromic transparent polymers

diary-HI

ΔGE→Z/ ΔGZ→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

  1. a in toluene-d8.
  2. bin o-xylene-d10..
  3. cin toluene/toluene-d8.
  4. dEquilibration half-life time of thermal isomerization, linearly extrapolated to 25 °C.
  5. eValues not determined due to photodegradation.
  6. fNo change during heating.
  7. gin THF-d8.