1

Electronic Supplementary Information (ESI)

Biindoles-based double D-π-A branched organic dyes for efficient dye-sensitized solar cells

Xing Qian, Huan-Huan Gao, Yi-Zhou Zhu,* Lin Lu and Jian-Yu Zheng*

State Key Laboratory and Institute of Elemento-Organic Chemistry, Collaborative Innovation

Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071, China;

Fax: +86-22-2350 5572; Tel: +86-22-2350 5572;

*E-mail: zhuyizhou@nankai.edu.cn; jyzheng@nankai.edu.cn.

Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2014

2

Fig. S1 1H NMR of compound 2 in acetone-d6.

0102030405060708090100110120130140150160170180190200210220f1 (ppm)

13.5

122

.44

25.8

728

.43

28.6

228

.81

29.0

029

.08

29.1

429

.19

29.3

929

.58

31.6

9

67.5

0

105.

8811

0.92

114.

2511

9.11

119.

5412

1.54

125.

8112

7.86

130.

3213

5.17

136.

71

158.

34

205.

36

Fig. S2 13C NMR of compound 2 in acetone-d6.

3

Fig. S3 1H NMR of compound 3 in CDCl3.

0102030405060708090100110120130140150160170180190200210f1 (ppm)

14.1

314

.16

22.6

422

.72

26.1

326

.74

27.6

229

.06

29.1

529

.33

29.4

629

.80

31.7

731

.88

43.8

667

.96

76.7

477

.06

77.3

7

107.

4210

9.62

113.

8211

8.91

120.

7212

0.96

124.

8912

9.56

131.

3613

6.54

138.

69

158.

05

Fig. S4 13C NMR of compound 3 in CDCl3.

4

Fig. S5 1H NMR of compound 4a in CDCl3.

0102030405060708090100110120130140150160170180190200210f1 (ppm)

14.1

014

.13

22.6

122

.69

26.1

026

.58

28.9

829

.09

29.2

929

.43

29.7

229

.87

31.7

331

.85

43.9

4

68.0

0

76.7

577

.07

77.3

8

106.

7210

7.06

107.

6111

4.05

117.

2612

0.69

121.

9612

4.03

130.

6613

1.14

136.

6014

1.46

151.

5615

8.50

161.

97

176.

63

Fig. S6 13C NMR of compound 4a in CDCl3.

5

Fig. S7 1H NMR of compound 4b in CDCl3.

0102030405060708090100110120130140150160170180190200210f1 (ppm)

14.1

414

.16

22.6

422

.71

26.1

226

.68

29.0

029

.12

29.3

129

.44

29.7

429

.85

31.7

531

.87

44.0

068

.01

76.7

777

.09

77.4

0

107.

4710

8.08

114.

0611

8.22

120.

8812

3.12

123.

9612

6.26

130.

5313

1.14

136.

7013

7.90

141.

1614

1.25

157.

0415

8.50

182.

66

Fig. S8 13C NMR of compound 4b in CDCl3.

6

Fig. S9 1H NMR of compound 4c in CDCl3.

-100102030405060708090100110120130140150160170180190200210f1 (ppm)

14.1

422

.65

22.7

026

.11

26.6

728

.99

29.1

229

.31

29.4

029

.44

29.7

329

.80

31.7

731

.86

43.9

1

68.0

1

76.7

377

.05

77.3

610

7.26

107.

4911

4.00

117.

9312

0.89

123.

2412

3.57

124.

2212

6.77

127.

3112

9.73

131.

1913

3.75

136.

7913

7.57

140.

5314

1.06

147.

7914

8.70

158.

37

182.

43

Fig. S10 13C NMR of compound 4c in CDCl3.

7

Fig. S11 1H NMR of compound JY11 in DMSO-d6.

0102030405060708090100110120130140150160170180190200210f1 (ppm)

14.3

214

.36

22.5

022

.55

25.9

626

.12

28.6

228

.94

29.0

129

.16

29.1

930

.86

31.5

931

.70

34.8

467

.68

96.1

6

107.

5410

9.22

114.

4611

7.26

117.

5612

0.32

121.

9912

3.83

125.

3613

0.01

131.

2713

6.76

137.

7013

9.64

141.

7214

7.31

158.

6016

1.34

164.

69

Fig. S12 13C NMR of compound JY11 in DMSO-d6.

8

Fig. S13 1H NMR of compound JY12 in DMSO-d6.

Fig. S14 13C NMR of compound JY12 in DMSO-d6.

9

Fig. S15 1H NMR of compound JY13 in DMSO-d6.

0102030405060708090100110120130140150160170180190200210f1 (ppm)

14.3

414

.37

22.5

022

.55

25.9

826

.14

28.6

628

.93

29.0

529

.16

29.2

129

.45

31.6

031

.71

43.4

067

.75

98.3

010

7.41

107.

9311

4.45

117.

1611

8.04

120.

3612

4.13

124.

7012

4.83

126.

5712

8.78

129.

4713

1.28

133.

1713

3.97

137.

0114

0.89

141.

9814

6.54

146.

6114

8.24

158.

5116

4.13

Fig. S16 13C NMR of compound JY13 in DMSO-d6.