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Proton transfer assisted facile encapsulation of 2,4,6-trinitrophenol in sol-gel derived silica decorated with azo-azomethine hosts
RuchiMutnejaa, RaghubirSinghb*, VarinderKaura*, JörgWaglerc, Edwin Krokec, Sushil Kumar Kansald
300 350 400 450 500 550 6000
1
2
3
4
300 350 400 450 500 550 6000
1
2
3
300 350 400 450 500 550 6000
1
2
3
Wavelength, nm
C
A
Abs
orba
nce,
AU
B
Figure S1 UV/Vis spectrum of equimolar mixture of host and guest with varying concentrations; A, 0.03 mM; B, 0.12 mM; C, 8mM of each host and guest [UV-Vis was recorded in 1cm cell; in C, the region below 400 nm became out of scale due to higher concentration of both host and guest so, omitted]
-111 10 9 8 7 6 5 4 3 2 1 0 ppm
0.0001
7.2628
9.2003
2.00
Current Data ParametersNAME Jul29-2015EXPNO 90PROCNO 1
F2 - Acquisition ParametersDate_ 20150729Time 16.47INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT CDCl3NS 8DS 2SWH 12019.230 HzFIDRES 0.183399 HzAQ 2.7263477 secRG 1150DW 41.600 usecDE 6.00 usecTE 298.0 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 10.90 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300086 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
3 BRUKERAVANCE II 400 NMRSpectrometerSAIFPanjab UniversityChandigarh
manishkumarmanu1986@gmail.com
Figure S21H-NMR of picric acid (PA)
a,bH
TMS
18 17 16 15 14 13 12 11 10 9 8 7 6 5 4 3 2 1 0 ppm
0.0690
0.4917
0.5118
0.5322
1.8671
1.8869
1.8993
1.9065
1.9134
1.9259
1.9457
2.5463
2.7968
2.8114
2.8259
3.5903
3.6063
3.6218
3.7489
3.7635
3.7781
6.8535
6.8767
7.2607
7.3595
7.3756
7.3936
7.4524
7.4723
7.4910
7.8057
7.8243
7.9601
7.9663
7.9832
7.9895
8.1208
8.1270
17.1372
2.01
2.08
3.00
6.20
2.16
6.23
1.00
1.18
2.15
1.95
1.00
1.03
1.01
Current Data ParametersNAME Jul29-2015EXPNO 70PROCNO 1
F2 - Acquisition ParametersDate_ 20150729Time 16.36INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT CDCl3NS 8DS 2SWH 12019.230 HzFIDRES 0.183399 HzAQ 2.7263477 secRG 456DW 41.600 usecDE 6.00 usecTE 298.0 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 10.90 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300093 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
1 BRUKERAVANCE II 400 NMRSpectrometerSAIFPanjab UniversityChandigarh
manishkumarmanu1986@gmail.com
(a)
5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm
0.06
90
0.49
170.
5118
0.53
22
1.86
711.
8869
1.89
931.
9065
1.91
341.
9259
1.94
57
2.54
63
2.79
682.
8114
2.82
59
3.59
033.
6063
3.62
183.
7489
3.76
353.
7781
2.01
2.08
3.00
6.20
2.16
6.23
Current Data ParametersNAME Jul29-2015EXPNO 70PROCNO 1
F2 - Acquisition ParametersDate_ 20150729Time 16.36INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT CDCl3NS 8DS 2SWH 12019.230 HzFIDRES 0.183399 HzAQ 2.7263477 secRG 456DW 41.600 usecDE 6.00 usecTE 298.0 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 10.90 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300093 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
1 BRUKERAVANCE II 400 NMRSpectrometerSAIFPanjab UniversityChandigarh
manishkumarmanu1986@gmail.com(b)
17
18 1419
1615
6.46.66.87.07.27.47.67.88.08.28.48.68.8 ppm
6.8535
6.8767
7.2607
7.3595
7.3756
7.3936
7.4524
7.4723
7.4910
7.8057
7.8243
7.9601
7.9663
7.9832
7.9895
8.1208
8.1270
1.00
1.18
2.15
1.95
1.00
1.03
Current Data ParametersNAME Jul29-2015EXPNO 70PROCNO 1
F2 - Acquisition ParametersDate_ 20150729Time 16.36INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT CDCl3NS 8DS 2SWH 12019.230 HzFIDRES 0.183399 HzAQ 2.7263477 secRG 456DW 41.600 usecDE 6.00 usecTE 298.0 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 10.90 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300093 MHzWDW EMSSB 0LB 0.30 HzGB 0PC 1.00
1 BRUKERAVANCE II 400 NMRSpectrometerSAIFPanjab UniversityChandigarh
manishkumarmanu1986@gmail.com(c)
Figure S3 (a) 1H-NMR host (H); (b) Magnified 1H-NMR host (H); (c) Magnified 1H-NMR host
2,611
8 12
CdCl3
3,4,5
-117 16 15 14 13 12 11 10 9 8 7 6 5 4 3 2 1 0 ppm
0.06
710.49
950.51
830.53
741.95
501.97
301.99
162.01
012.02
822.58
382.76
862.81
212.82
672.84
133.75
043.76
503.77
963.79
793.81
403.82
543.83
203.84
243.84
943.85
997.25
987.35
827.40
987.43
277.45
287.47
037.48
987.50
917.52
627.85
227.87
037.87
338.13
108.13
678.15
368.15
938.24
808.25
368.92
54
13.9
278
2.08
2.11
3.29
6.15
6.03
2.26
2.18
2.31
2.20
1.06
1.03
2.03
1.05
Current Data ParametersNAME Jul29-2015EXPNO 80PROCNO 1
F2 - Acquisition ParametersDate_ 20150729Time 16.42INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT CDCl3NS 8DS 2SWH 12019.230 HzFIDRES 0.183399 HzAQ 2.7263477 secRG 1030DW 41.600 usecDE 6.00 usecTE 298.1 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 10.90 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300098 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.00
2 BRUKERAVANCE II 400 NMRSpectrometerSAIFPanjab UniversityChandigarh
manishkumarmanu1986@gmail.com
11121314151617 ppm
(a)
4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 ppm
0.0671
0.4995
0.5183
0.5374
1.9550
1.9730
1.9916
2.0101
2.0282
2.5838
2.7686
2.8121
2.8267
2.8413
3.7504
3.7650
3.7796
3.7979
3.8140
3.8254
3.8320
3.8424
3.8494
3.8599
2.08
2.11
3.29
6.15
6.03
2.26
Current Data ParametersNAME Jul29-2015EXPNO 80PROCNO 1
F2 - Acquisition ParametersDate_ 20150729Time 16.42INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT CDCl3NS 8DS 2SWH 12019.230 HzFIDRES 0.183399 HzAQ 2.7263477 secRG 1030DW 41.600 usecDE 6.00 usecTE 298.1 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 10.90 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300098 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.00
2 BRUKERAVANCE II 400 NMRSpectrometerSAIFPanjab UniversityChandigarh
manishkumarmanu1986@gmail.com(b)
14
1716
1918
15
7.17.27.37.47.57.67.77.87.98.08.18.28.38.48.58.68.78.88.99.09.1 ppm
7.2598
7.3582
7.4098
7.4327
7.4528
7.4703
7.4898
7.5091
7.5262
7.8522
7.8703
7.8733
8.1310
8.1367
8.1536
8.1593
8.2480
8.2536
8.9254
2.18
2.31
2.20
1.06
1.03
2.03
Current Data ParametersNAME Jul29-2015EXPNO 80PROCNO 1
F2 - Acquisition ParametersDate_ 20150729Time 16.42INSTRUM spectPROBHD 5 mm PABBO BB-PULPROG zg30TD 65536SOLVENT CDCl3NS 8DS 2SWH 12019.230 HzFIDRES 0.183399 HzAQ 2.7263477 secRG 1030DW 41.600 usecDE 6.00 usecTE 298.1 KD1 1.00000000 secTD0 1
======== CHANNEL f1 ========NUC1 1HP1 10.90 usecPL1 -3.00 dBSFO1 400.1324710 MHz
F2 - Processing parametersSI 32768SF 400.1300098 MHzWDW EMSSB 0LB 1.00 HzGB 0PC 1.00
2 BRUKERAVANCE II 400 NMRSpectrometerSAIFPanjab UniversityChandigarh
manishkumarmanu1986@gmail.com(c)
Figure S4 (a)1H-NMR of host-guest interaction (b) Enlarged 1H-NMR of host-guest interaction (c) Enlarged 1H-NMR of host-guest interaction
CdCl3
3,4,5,112,6128
a,bH
Table S1 Data of UV-Visible spectrum for Phenol, NB, o-NT, p-NP, o-NP, 2,4-DNP
before and after adsorption on 20 mg of H@SM.
Different Phenols used
Initial concentration
(mM)
Wavelength (nm) Absorbance before adsorption
Absorbance After adsorption
Phenol 0.30 270 1.20 1.10NB 0.15 260 1.30 1.19
o-NT 0.20 274 1.51 1.45o-NP 0.20 345 0.58 0.49p-NP 0.20 310 2.10 1.68
2,4 DNP 0.20 292 1.18 0.31
Table S2 Selected Bond length (Å) and bond angles (°)
Parameter X-ray crystal data Si−O(3) 1.6689(15) Si−O(1) 1.6714(15)Si−O(2) 1.6756(15)Si−C(7) 1.887(2)Si−N(1) 2.1595(18)
N(2)−C(9) 1.467(6)C(7)−C(8) 1.535(3)C(8)−C(9) 1.523(3)
O(3)−Si(1)−O(1) 118.77(8)O(3)−Si(1)−O(2) 116.84(8)O(1)−Si(1)−O(2) 120.05(8)C(7)−Si(1)−O(1) 96.42(8)C(7)−Si(1)−O(2) 97.17(8)N(1)−Si(1)−O(1) 82.91(7)N(1)−Si(1)−O(2) 82.92(7)N(1)−Si(1)−O(3) 83.32(7)N(1)−Si(1)−C(7) 179.26(8)
Figure S5 I.R spectra of (A) SM (B) H@SM
Figure S6 TGA curve for (A) SM (B) H@SM (C) Host (H)
Figure S7 (A) Effect of weight of adsorbent at 298 K and (B) temperature variation from 15-45 °C on the adsorption of PA.
Figure S8 Adsorption and extraction of PA for consecutive five cycles
Figure S9 Comparison of uptake of analogues of PA by H@SM
Table S3 Comparison of adsorption capacity of silica decorated host for PA with
reported methods
S.No. Adorbent used Temp. (°C)
AgitationTime (h)
Qm (mgg-1) Ref
1 Silica decorated azo-azomethine host
25 - 68.5 This Study
2 Uncalcined Mesoporous silicate
25 - [21]
3 Magnetic iron oxide nanoparticles
25 0.033 46.3 [22]
4 (a) Activated carbon from almond shell
25/35/45 48 74.0/71.1/70.8 [23]
(b) Magnetic activated carbon from almond shell
25/35/45 48 73.9/84.0/87.1 [23]
(C) Calgon carbon 25/35/45 48 327.8/203.9/188.2 [23]5 Polymer–clay nanocomposite
(dry/wet)- 0.066/1 45.8/45.8 [24]
6 Amberlite IRA-67 25/35/45 1.5 31.8/38.6/47.1 [26]
7 Bagasse fly ash - 24 17.0 [61]
8 Hydrotalcite (HT)/ Calcined Hydrotalcite (HT-500)
- 1 199/520 [62]
9 Metal ferrocyanides (Cu/Zn/Mo/Cr)
40 24 35.7/47.6/62.5/34. [63]
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