Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2001
Supplementary Information
for
More than just a catalyst: a novel role for benzylamine in the sol-gel transcription of
organogels.
Arianna Friggeri,a Oliver Gronwald,a Kjeld J. C. van Bommel,a Seiji Shinkai *a and David
N. Reinhoudt*b
50
40
1
CD [mdeg]
30
1 + benzylamine
20
10
0
200
-10
220
240
260
280
300
320
340
360
380
400
wavelength [nm]
Figure 1. CD spectra of a gel of 1 and of 1 + b.a.
The difference in intensity between these two CD spectra is significant since both
samples were prepared with the same concentrations of 1 and were measured with the
same cell (path length = 0.1 mm). The decrease in spectral intensity for the gel of 1 and
benzylamine cannot be attributed to the inset of crystallization of the sample in the cell
(as sometimes occurs), since repeated measurements of the same sample at different time
intervals did not show changes in the shape or the intensity of the spectrum.
Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2001
Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2001
4000
3500
3000
2500
2000
2526
A (a.u.)
A (a.u.)
4500
4500
4000
3500
4500
4000
3500
3000
2500
2000
3000
2500
2000
d
A (a.u.)
3254
3415
c
A (a.u.)
Absorbance (a.u.)
3377
b
3532
3337
a
4000
3500
3000
2500
2000
4500
-1
wavelength [cm ]
3482
Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2001
Figure 2. FT-IR spectra of amorphous compound 1 (a), amorphous compound 1 + b.a. (b),
xerogel of 1 (c) and xerogel of 1 + b.a. (d).
FT-IR spectra (KBr pellet) of amorphous compound 1 and of amorphous compound 1 +
b.a. were also measured (Figures 2a and 2b, respectively). Only the H-bonding region of
the FT-IR spectra is shown since it provides the most important information about the
intermolecular arrangement. In the spectrum of amorphous compound 1 (Figure 2a) both
free (sharp peak at 3532 cm-1) and H-bonded (broad peak at 3337 cm-1) OH groups
belonging to the glucose moiety are present. However, in the xerogel of 1 (Figure 2c), the
more ordered packing of the molecules in the gel with respect to the amorphous solid
leads to only one, broad peak at around 3415 cm-1, corresponding to H-bonded OH
groups.1 The spectrum of amorphous compound 1 + b.a. (Figure 2b) is similar to that of
amorphous compound 1 alone (Figures 2a), with the additional vibrations for the free and
H-bonded NH group of the benzylamine (sharp peak at 3377 cm-1 and broad peak at 2526
cm-1, respectively).
Supplementary Material (ESI) for Chemical Communications
This journal is © The Royal Society of Chemistry 2001
b.a.
343
1 : 1.0
333
1 : 1.0
323
1 : 1.8
313
1 : 2.9
303
1 : 2.9
298
1 : 1.5
 / ppm 9.0
8.5
8.0
7.5
1 : b.a.
T/K
1
7.0
Figure 3. Temperature dependent 1H NMR spectra showing the aromatic protons
region for 1 + b.a. (gel at 298 K, sol at 343 K); the molecular ratio of 1 : b.a. is shown on
the right of each spectrum, as determined from the integrals of the corresponding NMR
peaks.
1
K. Inoue, Y. Ono, Y. Kanekiyo, T. Ishi-i, K. Yoshihara and S. Shinkai, J. Org. Chem.,
1999, 64, 2933; K. Yoza, N. Amanokura, Y. Ono, T. Akao, H. Shinmori, M. Takeuchi, S.
Shinkai and D. N. Reinhoudt, Chem. Eur. J., 1999, 5, 2722; N. Amanokura, K. Yoza, , H.
Shinmori, S. Shinkai and D. N. Reinhoudt, J. Chem. Soc., Perkin Trans. 2, 1998, 2585.