Table 1 Overview of the photophysical and physical properties of HPIs 1-18. All experiments were performed in toluene-d8 or p-xylene-d10 unless stated otherwise

From: Hemiphosphoindigos as a platform for chiroptical or water soluble photoswitching

HPI

ΔG‡E→Z [kcal mol–1]

Half-life of E isomer at 25 °Ca

ΔG [kcal mol–1]

ϕZ→E & ϕE→Z

Isomer % in pss (at irr. wavelength)

εmax [L mol–1 cm–1] and λ [nm] at εmax of Z and E isomers

1

>35.5

>380000 a

>1.5b

50% &

1%

88% E (395 nm)

98% Z (450 nm)

Z: 341; 3800

E: 344; 5500

2

>35.0

>165000 a

>1.8b

40% &

10%

80% E (300 nm)

100% Z (450 nm)

Z: 330; 5300

E: 338; 8500

3

28.8

4 a

2.4

52% &

24%

82% E (395 nm)

98% Z (470 nm)

Z: 391; 29,600

E: 377; 11,800

3-OH

21.1

6 min

1.8

9% &

7%

63% E (405 nm)

92% Z (470 nm)

Z: 403; 23,300

E: 414; 11,000

4

30.3

50 a

1.9

47% &

21%

79% E (395 nm)

99% Z (450 nm)

Z: 358; 22,400

E: 346; 12,500

5

33.5

11500 a

1.7

37% &

9%

68% E (395 nm)

98% Z (450 nm)

Z: 357; 5500

E: 358; 8700

6

30.0

30 a

1.6

45% &

23%

81% E (395 nm)

98% Z (470 nm)

Z: 339; 10,800

E: 334; 8100

7

26.5

33 a

1.4

3% &

2%

47% E (430 nm)

91% Z (530 nm)

Z: 449; 9100

E: 481; 16,000

8

22.7

1.4 h

2.3

21% &

22%

31% E (470 nm)

99% Z (565 nm)

Z: 485; 62,500

E: 495; 53,100

9

22.0

25 min

3.1

26% &

23%

41% E (450 nm)

93% Z (505 nm)

Z: 456; 53,600

E: 464; 46,900

10

29.0

7 a

3.1

51% &

18%

65% E (365 nm)

98% Z (470 nm)

Z: 372; 25,800

E: 373; 26,400

11

27.6

210 d

3.3

46% &

30%

66% E (340 nm)

99% Z (450 nm)

Z: 332; 30,500

E: 334; 22,300

12

29.5

15 a

2.6

48% &

30%

60% E (340 nm)

97% Z (450 nm)

Z: 328; 27,600

E: 328; 24,900

13

27.7

260 d

3.4

51% &

49%

53% E (340 nm)

98% Z (450 nm)

Z: 322; 21,000

E: 328; 18,100

14

28.1

1.5 a

2.9

36% &

59%

53% E (365 nm)

98% Z (450 nm)

Z: 332; 18,000

E: 327; 15,500

15

24.0

3 d

1.2

29% &

33%

69% E (365 nm)

99% Z (450 nm)

Z: 383; 24,400

E: 414; 21,700

16

26.4

5 d

0.7

12% &

14%

66% E (395 nm)

99% Z (470 nm)

Z: 430; 46,300

E: 450; 38,100

17

29.5

14 a

1.0

30% &

12%

84% E (340 nm)

100% Z (450 nm)

Z: 372; 30,100

E: 402; 22,000

18

22.2

34 min

2.6

35% &

11%

63% E (430 nm)

60% Z (470 nm)

Z: 424; 23,700

E: 430; 23,400

  1. aLinearly extrapolated. bValue estimated before full completion of thermal isomerization, since the experiment is very slow and not finished within a reasonable time.
  2. For hydrolyzed HPI 3-OH, all experiments were performed in D2O.
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