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Supporting Information
Stimuli Responsive hydrogel derived from Renewable Resource: Synthesis, Self-Assembly in water and application
in drug deliveryKrishnamoorthy Lalitha,a Y. Siva Prasad,a C. Uma Maheswari,a Vellaisamy Sridharan,a George John,b Subbiah Nagarajan*a
a Organic Synthesis Group, Department of Chemistry & The Centre for Nanotechnology and
Advanced Biomaterials, School of Chemical and Biotechnology, SASTRA University, Thanjavur
- 613401, Tamil Nadu, INDIA Fax: 04362264120; Tel: 04362304270; E-mail:
nagarajan@scbt.sastra.edu.b Department of Chemistry, the City College of New York. 160 Convent Ave. New York, NY 10031.
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B.This journal is © The Royal Society of Chemistry 2015
Table S1: Vegetable oil/Solvent used for gelation studies
S.No Oil/Solvent 4a 4b 4c
1 Hazelnut P P P
2 Sesame P P P
3 Jojoba P P P
4 Olive P P P
5 Soyabean P P P
6 Linseed P S S
7 Light paraffin P P P
8 Heavy paraffin P PG PG
9 Dodecanol I S S
10 Ethanol P P S
11 n-Butanol P S S
12 Octanol P S S
13 Toluene I I I
14 Cyclohexane I I I
15 n-heptane I I I
16 Ethylene glycol I I I
17 Ethanol+water S S PG
18 DMSO S S S
19 DMF S S S
20 DMSO+water S PG G
DMF+water S S S
S – Soluble; I – Insoluble; P – Precipitation; PG – Partial gel formation
Calculated quantity of gelator was taken in a separate glass vial and about 20-30 μL of
DMSO was added. The vials were heated to dissolve the compounds and then distilled water was
added drop wise. The formation of cloudy white solution was observed which was again heated to
get clear homogeneous solution and cooled to room temperature to form hydrogel. Gel formation
has been observed within 5-6 h. The thermorevesibility of these gels were confirmed by repeating
heating and cooling experiments.
Figure S1 Photograph of the hybrid hydrogel formed from compound 4c.
Figure S2. Morphology of self-assembled fibers formed from 4c in acidic pH.
Figure S3 - Zetasizer report of 4c, average diameter of micelles is 197nm
Figure S4. Photographs of the gel (a) without curcumin (B) with curcumin drug (C) curcumin
loaded gel in acidic buffer pH 4
Position [°2Theta] (Copper (Cu))20 30 40 50 60 70
Counts
0
100
200
300
A-D
Figure S5. WAXD data for gel.
1.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
1
2
Figure S6. 1H NMR spectra of (a) gelator, 4c in DMSO-d6 and (b) gel formed by 4c in DMSO-d6-D2O (1:2
ratio).
(a)
(b)
Copies of 1H and 13C spectra
01234567891011f1 (ppm)
-0.0
01
0.85
40.
878
0.89
91.
252
1.25
91.
271
1.29
01.
300
1.59
11.
641
1.95
01.
965
1.97
61.
984
1.99
92.
010
2.01
92.
034
2.04
52.
587
2.61
22.
638
5.32
55.
334
5.34
45.
355
5.36
45.
379
5.39
3
6.80
16.
821
6.84
7
7.43
07.
456
9.82
7
11.0
47
OHCH3
O
020406080100120140160180200f1 (ppm)
14.1
222
.67
27.1
727
.24
29.0
029
.16
29.2
129
.25
29.3
429
.44
29.6
329
.67
29.7
229
.74
30.6
631
.80
32.6
236
.44
117.
0711
8.85
120.
50
129.
7413
0.00
133.
58
153.
78
161.
80
195.
80
OHCH3
O
01234567891011f1 (ppm)
-0.0
02
0.85
40.
877
0.89
81.
287
1.30
31.
318
1.33
91.
566
1.58
81.
614
1.63
91.
663
2.58
62.
612
2.63
8
6.80
26.
817
6.82
26.
843
6.84
8
7.43
27.
458
9.82
9
11.0
45
OH
CH3
O
020406080100120140160180200f1 (ppm)
14.1
3
22.7
129
.25
29.3
829
.44
29.5
429
.67
29.7
130
.67
31.9
436
.45
117.
0711
8.84
120.
49
133.
57
153.
82
161.
79
195.
78OH
CH3
O
01234567891011f1 (ppm)
0.00
0
0.78
40.
808
0.83
11.
192
1.21
61.
240
1.31
71.
341
1.35
11.
364
1.60
41.
901
1.93
01.
950
2.62
02.
646
2.67
1
4.30
74.
331
4.35
44.
378
5.27
35.
276
5.30
5
7.06
77.
073
7.09
67.
423
7.42
87.
451
8.44
9
O
O
O
OCH3
CH3
020406080100120140160180200f1 (ppm)
14.2
322
.63
27.1
227
.19
28.9
529
.11
29.1
529
.34
29.6
629
.69
30.8
336
.26
41.6
5
61.4
761
.80
77.2
7
115.
7211
6.19
116.
88
125.
4712
9.22
129.
6712
9.99
148.
7115
1.30
155.
4015
7.01
163.
25
166.
60
O
O
O
OCH3
CH3
01234567891011f1 (ppm)
0.00
0
0.80
80.
827
0.85
01.
182
1.23
41.
318
1.34
21.
365
2.61
92.
645
2.67
1
4.30
84.
332
4.35
64.
379
7.07
47.
097
7.20
17.
422
7.42
77.
445
7.45
0
8.45
0
O
O CH3
O
OCH3
020406080100120140160180200f1 (ppm)
1.02
14.1
214
.24
22.6
929
.19
29.3
629
.41
29.5
229
.62
29.6
529
.69
30.8
531
.92
36.2
9
61.8
3
115.
7311
6.20
125.
50
129.
23
148.
7515
1.33
155.
4115
7.06
163.
26
O
O CH3
O
OCH3
01234567891011f1 (ppm)
-0.0
00
3.66
63.
684
4.82
94.
848
4.86
6
7.43
17.
456
7.48
17.
521
7.54
87.
737
7.74
27.
765
7.77
07.
789
7.79
47.
987
7.99
28.
013
8.01
8
8.92
98.
984
O
NH
OH
OH
OH
O
O
01234567891011f1 (ppm)
0.00
00.
011
0.88
8
1.25
41.
319
1.90
0
2.73
72.
759
3.80
13.
808
5.30
55.
316
7.20
17.
267
7.27
67.
282
7.57
47.
602
8.86
3
9.73
5
O
NH
OH
OH
OH
O
OCH3
-20020406080100120140160180200f1 (ppm)
13.1
1
21.6
526
.23
28.1
928
.37
28.7
129
.84
30.7
435
.32
61.3
261
.68
76.2
8
115.
0511
5.36
115.
93
125.
00
128.
70
147.
7115
0.38
153.
74
160.
4216
2.04
O
NH
OH
OH
OH
O
OCH3
01234567891011f1 (ppm)
0.00
0
0.85
20.
875
0.89
6
1.32
0
1.64
01.
666
2.71
92.
744
2.77
0
3.73
33.
752
4.82
74.
848
7.15
97.
184
7.21
6
7.63
57.
662
8.87
5
9.53
2O
NH
OH
OH
OH
O
OCH3
020406080100120140160180200f1 (ppm)
13.6
6
22.0
828
.59
28.7
328
.80
28.9
129
.03
29.0
630
.30
31.3
135
.69
38.7
4
61.6
862
.34
115.
3411
5.85
116.
88
125.
50
129.
21
147.
7815
0.59
154.
15
160.
6516
2.01
O
NH
OH
OH
OH
O
OCH3
Mass spectra of compound 4b
Mass spectra of Compound 4c