Table 1 Optimization of C-S cleavage polycondensation conditions for the synthesis of semiconducting polymer P1 from E1 + N1a.

From: Efficient room temperature catalytic synthesis of alternating conjugated copolymers via C-S bond activation

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Entry

[Pd] Catalyst

[Cu] Cocatalyst

Solvent

T (oC)

Time (h)

Mn/Mw (kDa)

Đ

Yieldb (%)

1

Pd(PPh3)4

CuTc

Toluene

100

24

14.5/70.0

4.82

84

2

Pd(PPh3)4

CuTc

Toluene

60

24

14.3/48.7

3.39

81

3

Pd(PPh3)4

CuTc

Toluene

RT

24

15.7/49.5

3.15

84

4

Pd(PPh3)4

CuTc

Toluene

0

24

7.4/23.4

3.17

24

5

Pd(PPh3)4

CuTc

Toluene

RT

12

15.1/73.3

4.85

60

6

Pd(PPh3)4

CuTc

Toluene

RT

72

15.9/60.5

3.81

70

7c

Pd(PPh3)4

CuTc

Toluene

RT

24

4.7/12.2

2.62

62c

8d

Pd(PPh3)4

CuTc

Toluene

RT

24

3.7/7.9

2.10

80d

9

Pd(PPh3)4

CuMeSal

Toluene

RT

24

7.8/20.9

2.67

52

10

Pd(PPh3)4

CuI

Toluene

RT

24

-

-

0

  1. Reaction conditions: aPd catalyst (10 mol%), Cu cocatalyst (5 equiv.), E1 (1 equiv, 0.025 M) and N1 (1 equiv, 0.025 M) in solvent under N2.
  2. bYield collected from chloroform fraction.
  3. cPd(PPh3)4 (5 mol%); yield collected from hexane fraction.
  4. dCuTc (2.5 equiv.); yield collected from hexane fraction.
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