Supplementary Material (ESI) for Journal of Materials Chemistry
This journal is © The Royal Society of Chemistry 2001
Behavior of organic compounds confined in sol-gel silica glass. Effects of
guest-host hydrogen bonding on uptake, release, and isomerization of the
guest compounds
Jovica D. Badjić and Nenad M. Kostić*
Department of Chemistry, Iowa State University, Ames, IA 50010, USA
Supporting Information
Supplementary Material (ESI) for Journal of Materials Chemistry
This journal is © The Royal Society of Chemistry 2001
Table S1. Ultraviolet absorptivities of trans and cis isomers of azobenzene derivatives.
compound
3,3′-dimethyl
azobenzene

 trans (M-1cm-1)
trans
cis
symbol
wavelength (nm)
A
324.6
21474
1317
3-acetyl
azobenzene
B
320.0
19516
1931
3,3′-diacetyl
azobenzene
C
320.0
19354
2012
3,5-diacetyl
azobenzene
D
319.0
20243
1006
E
314.0
16896
2623
3,3′,5,5′tetraacetyl
azobenzene
Supplementary Material (ESI) for Journal of Materials Chemistry
This journal is © The Royal Society of Chemistry 2001
2.0
1.8
1.6
1.4
A
1.2
1.0
0.8
0.6
0.4
0.2
0.0
280
290
300
310
320
330
Wavelength (nm)
Figure S1. Absorption spectrum of styrene in solution (solid line) and inside sol-gel silica glass
(dashed line). In both cases solvent was in CCl4. Lack of perturbation of the spectrum is evidence
against hydrogen bonding between styrene and silica.
Supplementary Material (ESI) for Journal of Materials Chemistry
This journal is © The Royal Society of Chemistry 2001
1.8
1.6
1.4
1.2
A
1.0
0.8
0.6
0.4
0.2
0.0
272
280
288
296
304
Wavelength (nm)
312
320
Figure S2. Absorption spectra of N,N-diethyl-p-anisidine in solution (dash-dotted line) and
inside sol-gel silica glass (solid line), in both cases in a 9 : 1 v/v mixture of CCl4 and DMF, and inside
sol-gel silica glass in CCl4 (dashed line).
Supplementary Material (ESI) for Journal of Materials Chemistry
This journal is © The Royal Society of Chemistry 2001
a
0.8
A
0.6
0.4
0.2
0.0
b
1.2
A
0.8
0.4
0.0
280
290
300
310
320
330
340
Wavelength (nm)
Figure S3. Absorption spectra a compound in solution (dashed line) and inside
trimethylsilylated sol-gel silica glass (solid line); in both cases the solvent is CCl4. The compound is
(a) aniline and (b) N,N-diethyl-p-anisidine.
Supplementary Material (ESI) for Journal of Materials Chemistry
This journal is © The Royal Society of Chemistry 2001
2.4
2.0
a
A280
1.6
1.2
0.8
0.4
0.0
0
40
80
120
160
200
240
Time (min)
2.0
b
A282
1.6
1.2
0.8
0.4
0.0
0
20
40
60
80
100
120
140
Time (min)
Figure S4. Uptake of (a) aniline and (b) N,N-diethyl-p-anisidine by sol-gel silica glass
when it is capable of hydrogen bonding to the guest compounds. The silica glass before the
uptake experiments was treated with HCl (), NaOH (), or neither compound (). Glass
Supplementary Material (ESI) for Journal of Materials Chemistry
This journal is © The Royal Society of Chemistry 2001
monolith sized 8 x 8 x 27 mm is soaked in 50.0 mL solution of each solute in CCl4. The dashed
line marks the absorbance of the external solution.
Figure S5. 1H NMR spectrum of 3,5-diacetyl azobenzene in CDCl3.
Supplementary Material (ESI) for Journal of Materials Chemistry
This journal is © The Royal Society of Chemistry 2001
Figure S6. 13C NMR spectrum of 3,5-diacetyl azobenzene in CDCl3.
Supplementary Material (ESI) for Journal of Materials Chemistry
This journal is © The Royal Society of Chemistry 2001
Figure S7. Low-resolution mass spectrum (CI) of 3,5-diacetyl azobenzene.
Supplementary Material (ESI) for Journal of Materials Chemistry
This journal is © The Royal Society of Chemistry 2001
Figure S8. 1H NMR of 3,3,5,5-tetraacetyl azobenzene spectrum in CDCl3.
Supplementary Material (ESI) for Journal of Materials Chemistry
This journal is © The Royal Society of Chemistry 2001
Figure S9. 13C NMR of 3,3,5,5-tetraacetyl azobenzene in CDCl3.
Supplementary Material (ESI) for Journal of Materials Chemistry
This journal is © The Royal Society of Chemistry 2001
Figure S10. Low-resolution mass spectrum (CI) of 3,3,5,5-tetraacetyl azobenzene.
Supplementary Material (ESI) for Journal of Materials Chemistry
This journal is © The Royal Society of Chemistry 2001