Structurally simple azo based chromogenic receptor for the selective sensing of cyanide ion

in aqueous medium

Palanisamy Kalpana, Sivalingam Suganya, Sivan Velmathi*

Organic and Polymer Synthesis Laboratory,

Department of Chemistry, National Institute of Technology,

Tiruchirappalli-620 015, INDIA. *E-mail: velmathis@nitt.edu, svelmathi@hotmail.com

List of figures

Fig.S1. IR Spectrum of R1.

Fig.S2. 1H NMR (400 MHz, DMSO-d6) spectrum of R1.

Fig.S3. 13C NMR (100 MHz, DMSO-d6) spectrum of R1.

Fig.S4. ESI Mass spectrum of R1.

Fig.S5. Elemental Analysis Data

Fig.S6. ESI Mass spectrum of R1-CN-

Fig.S1. IR Spectrum of R1.

Fig.S2. 1H NMR (400 MHz, DMSO-d6) spectrum of R1

13 12 11 10 9 8 7 6 5 4 3 2 1 ppm

7.13

17.

158

7.55

67.

581

7.67

97.

871

8.00

68.

293

8.81

7

11.6

73

12.3

79

0.99

3.01

5.00

1.01

3.30

0.78

0.85

R2

Fig.S3. 13C NMR (100 MHz, DMSO-d6) spectrum of R1.

190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm

31.14

117.40

117.76

120.29

122.01

122.76

123.37

125.93

126.71

127.23

129.87

130.39

131.37

140.44

145.61

147.46

150.07

150.86

152.48

155.84

159.90

160.65

162.00

162.45

R2 C13

Fig.S4. ESI Mass spectrum of R1

R2

m/z100 150 200 250 300 350 400 450 500 550 600 650 700 750 800 850 900 950

%

0

10020150519019 11 (0.753) Cn (Cen,3, 50.00, Ht); Sm (Mn, 2x0.75); Sb (3,50.00 ); Cm (10:14-1:7x3.000) Scan ES+

7.29e6346.2

106.1328.2

347.2

348.2

Fig.S5. Elemental Analysis Data

Elemental Analyzer Data Sheet

Korea Basic Science Institute

Daejeon Headquarter Analytical Lab.

169-148 Gwahak-ro, Yuseong-gu, Daejeon

Tel. 042-865-3490 Fax. 02-6943-4189

Date : 2016 년 7 월 1 일

Requester : 문 지 훈

Department : Instrument : Elemental Analyzer (Flash EA 2000series/ ThermoFisher)

Analyst : 서 정 주 / 도 지 훈

Remark

Standard : - BBOT : (C 72.58%, N 6.53%, H 6.05%, S 7.42%, O 7.42%)

Sampling weight : 2.0mg 내외

Combustion 온도 : - NCHS : 900C, - O : 1060C

Elemental analysis Found C 65.73 N 20.33 H 4.56 O 9.38, Calculated C 66.08 N 20.28 H 4.38 O 9.27.

Fig.S6. ESI Mass spectrum of R1-CN-

4x10

0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1

1.1

1.2

1.3

1.4

1.5

C19 H14 N5 O2: -ESI Scan (0.077 min) Frag=175.0V Azo-iso-CN-neg.d

344.1144[C19 H14 N5 O2]-

345.1181[C19 H14 N5 O2]-

346.1208[C19 H14 N5 O2]-

Counts vs. Mass-to-Charge (m/z)339.5 340 340.5 341 341.5 342 342.5 343 343.5 344 344.5 345 345.5 346 346.5 347 347.5 348 348.5 349 349.5 350 350.5 351 351.5 352 352.5 353 353.5 354