Electronic Supporting Information
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1 Electronic Supporting Information Microstructured Objects Produced by the Supramolecular Hierarchical Assembly of an Organic Free Radical gathering Hydrophobic-Amphiphilic Characteristics F. Vera, M. Mas-Torrent, J. Esquena, Y. Shen, T. Nakanishi, C. Rovira, and J. Veciana* Table of Contents S1.- Elemental Analysis of Compound 1. S2.- Particle Size (Dynamic light scattering) S3.- X-Ray Diffraction (SAXS and WAXS) S4.- FT-IR spectra S5.- Differencial Scaning Calorimetry (DSC) S6.- Electron Paramagnetic Resonance (EPR) - 1 -
2 S1.- Elemental Analysis of Compound 1. Molecular formula: C 87 H 127 Cl 14 O 3 EA calculated: C (60.85%); H (7.45%); Cl (28.90%) EA found: C (60.91%); H (4.470%); Cl (28.99%) S1.- Particle Size (Dynamic light scattering) Particle Size measurements were made with a Mastersizer 2000 instrument (Malver Instruments) with a Hydro2000μP accessory. All the samples were dispersed in iproh and sonicated 20 min at approx. 10ºC. The accessory was replenished until get obscuration around 5%. Precipitate from 1-hexanol volume (%) Precipitate from 1,4-dioxane particle size (μm) volume (%) particle size (μm) - 2 -
3 Precipitate from 1,4-dioxane/acetonitrile (3/1) volume (%) particle size (μm) Precipitate from dioxane/methanol (1/1) volume (%) Precipitate from isopropanol particle size (μm) volume (%) particle size (μm) - 3 -
4 Precipitate from THF/water (2/1) volume (%) particle size (μm) The shape and size of these assemblies were also studied by a statistic analysis with a Morphologi G3S instrument (Malvern). Suspensions of the samples were drop cast on a glass substrate. The x20 objective counted different objects. Most of them exhibited a diameter size in the range 1,5-7 μm and had circular shapes. It was observed that the second peak observed in the light scattering measurements that corresponds to larger particle diameters can be clearly attributed to the formation of particle aggregates
5 This graphic shows some of the microobjects detected in the region under the Gaussian curve: The next graphic shows some of the aggregates that correspond to the maximum (in volume) detected, due to the agreggation of several microobjects: - 5 -
6 Precipitate from toluene/ethanol (1/1) volume (%) Precipitate from toluene/methanol (1/1) particle size (μm) volume (%) particle size (μm) - 6 -
7 S2.- X-Ray Difraction (SAXS and WAXS) X-ray diffraction measurements were carried out in 1mm-diameter capillaries. Samples were measured during its first heating-cooling cycle, first measuring at 25ºC, than at 85ºC, cooling down to 40ºC and finally measuring again at 25ºC. Time of irradiation was 2 hours, in which temperature was kept constant. The equilibration time between determinations was 30 min in every case. Titles correspond to the solvents used to obtain the microobjects. SAXS and WAXS difractograms of precipitates form 1-hexanol: 25 o C before thermal treatment 25 o C after thermal treatment counts q (nm -1 ) counts q (nm -1 ) - 7 -
8 SAXS and WAXS difractograms of precipitates form 1,4-dioxane: o C before thermal treatment 25 o C after thermal treatment counts q (nm -1 ) counts q (nm -1 ) - 8 -
9 SAXS and WAXS difractograms of precipitates form isopropanol (SAXS): 25 o C before thermal treatment 25 o C after thermal treatment 1000 counts q (nm -1 ) counts q (nm -1 )
10 SAXS and WAXS difractograms of precipitates form 1,4-dioxane/acetonitrile (3/1): o C before thermal treatment 25 o C after thermal treatment counts q (nm -1 ) counts q (nm -1 )
11 SAXS and WAXS difractograms of precipitates form 1,4-dioxane/methanol 2/1: o C after thermal treatment 25 o C before thermal treatment counts q (nm -1 ) counts q (nm -1 )
12 SAXS and WAXS difractograms of precipitates form THF/water (2/1): o C before thermal treatment 25 o C after thermal treatment counts q (nm -1 ) counts q (nm -1 )
13 SAXS and WAXS difractograms of precipitates form toluene/methanol (1/1): o C before thermal treatment 25 o C after thermal treatment counts q (nm -1 ) counts q (nm -1 )
14 S3.- FT-IR spectra Precipitate from 1-hexanol: Precipitate from 1,4-dioxane:
15 Precipitate from 1,4-dioxane/acetonitril (3/1): Precipitate from dioxane/methanol (3/1):
16 Precipitate from isopropanol: Precipitate from THF/water (2/1):
17 Precipitate from toluene/ethanol (1/1): Precipitate from toluene/ethanol (1/1):
18 S4.- DSC thermograms DSC thermograms were recorded using a temperature ramp of 10ºC/min starting from 25ºC. In diagrams are represented the peak observed in the first heating cycle, corresponding to the nanostructured microobjects. From 1-hexanol: heat flow (exo down, mw) From 1,4-dioxane: temperature (ºC) heat flow (exo down, mw) temperature (ºC)
19 From dioxane/acetonitrile (3/1): heat flow (exo down, mw) temperature (ºC) From dioxane/methanol (2/1): heat flow (exo down, mw) temperature (ºC)
20 From isopropanol: heat flow (exo down, mw) temperature (ºC) From THF/water (2/1): heat flow (exo down, mw) temperature (ºC)
21 From toluene/ethanol (1/1): heat flow (exo down, mw) temperature (ºC) From toluene/methanol (1/1): heat flow (exo down, mw) temperature (ºC)
22 S5.- Thermogravimetry (TG) From 1-hexanol: From 1,4-dioxane: TG/% From 1,4-dioxane/acetonitrile (3/1): From 1,4-dioxane/methanol (2/1): From isopropanol:
23 From THF/water (2/1): TG/% From toluene/methanol: From toluene/ethanol:
24 S6.- EPR spectra From 1-hexanol: field (G) From 1,4-dioxane:
25 field (G) From 1,4-dioxane/acetonitrile (3/1): field (G) From 1,4-dioxane/methanol (2/1)
26 field (G) From isopropanol: field (G) From THF/water (2/1):
27 field (G) From toluene/methanol: field (G) From toluene/ethanol:
28 field (G)
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