Supporting Information Insight into the Chiral Induction in
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Supporting Information Insight into the Chiral Induction in Supramolecular Stacks through Preferential Chiral Solvation Subi J. George, a,b Željko Tomović, a Albertus P.H.J. Schenning* a and E.W. Meijer* a a Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P. O. Box 513, 5600 MB Eindhoven, The Netherlands. E-mail: [email protected] , [email protected] b Supramolecular Chemistry Laboratory, New Chemistry Unit, Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR), Bangalore, India-560064 General Methods Optical spectroscopy. UV-vis and Circular Dichroism measurement were performed on a Jasco J-815 spectropolarimeter where the sensitivity, time constant and scan rate were chosen appropriately. Corresponding temperature dependent measurements were performed with a PFD-425S/15 Peltier-type temperature controller with a temperature range of 263-383 K and adjustable temperature slope. Atomic Force Microscopy (AFM). AFM images were recorded under ambient conditions using a Digital Instrument Multimode Nanoscope IV operating in the tapping mode regime. Microfabricated silicon cantilever tips (NS) with a resonance frequency of approximately 300 kHz and a spring constant of about 50 Nm -1 were used. Mica substrates were freshly cleaved before use.
Transcript of Supporting Information Insight into the Chiral Induction in
Supporting Information
Insight into the Chiral Induction in Supramolecular Stacks through Preferential Chiral Solvation Subi J. George, a,b Željko Tomović,a Albertus P.H.J. Schenning*a and E.W. Meijer*a
a Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, P. O. Box 513, 5600 MB Eindhoven, The Netherlands. E-mail: [email protected], [email protected] b Supramolecular Chemistry Laboratory, New Chemistry Unit, Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR), Bangalore, India-560064 General Methods Optical spectroscopy. UV-vis and Circular Dichroism measurement were performed on a
Jasco J-815 spectropolarimeter where the sensitivity, time constant and scan rate were
chosen appropriately. Corresponding temperature dependent measurements were
performed with a PFD-425S/15 Peltier-type temperature controller with a temperature
range of 263-383 K and adjustable temperature slope.
Atomic Force Microscopy (AFM). AFM images were recorded under ambient
conditions using a Digital Instrument Multimode Nanoscope IV operating in the tapping
mode regime. Microfabricated silicon cantilever tips (NS) with a resonance frequency of
approximately 300 kHz and a spring constant of about 50 Nm-1 were used. Mica
substrates were freshly cleaved before use.
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2011
300 400 500 6000.0
0.5
1.0
1.5
Abs
orba
nce
Wavelength/nm
90 oC 20 oC
Fig S1. Absorption spectra of A-OPV4UT (2 x 10-4 M) in R-citronellol at molecularly dissolved state (90 oC) and at the self-assembled state (20 oC).
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2011
a) b)
c) d)
300 400 5000.0
0.5
1.0
263 K
303 K
303 K
Abso
rban
ce
Wavelength/nm
353 K
300 400 500-30
-15
0
15
30
Wavelength/nm
CD
/mde
g
298 K 293 K 288 K 283 K 278 K 273 K 268 K 263 K
300 400 500-30
-15
0
15
30
CD
/mde
g
Wavelength/nm
R-Citronellol S-Citronellol
280 300-20
-10
0
10
20 R-Citronellol S-Citronellol
CD
/mde
g
Temperature / K
a) b)
c) d)
300 400 5000.0
0.5
1.0
263 K
303 K
303 K
Abso
rban
ce
Wavelength/nm
353 K
300 400 500-30
-15
0
15
30
Wavelength/nm
CD
/mde
g
298 K 293 K 288 K 283 K 278 K 273 K 268 K 263 K
300 400 500-30
-15
0
15
30
CD
/mde
g
Wavelength/nm
R-Citronellol S-Citronellol
280 300-20
-10
0
10
20 R-Citronellol S-Citronellol
CD
/mde
g
Temperature / K
Fig S2. Temperature dependent a) absorption and b) CD spectra of A-OPV3UT in R-citronellol at an interval of 5 K when cooled from 353 K to 263 K. c) Mirror image CD spectra and d) cooling curves of A-OPV3UT in enantiomeric citronellol chiral solvents. The cooling curves are obtained by monitoring the CD intensity at 420 nm (2 x 10-4 M, dT/dt = - 60 K/hr). The difference in CD intensity could be due to the difference in enantiomeric excess (ee); ee of R-citronellol is 98% and that of S-citronellol is > 99%.
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2011
300 400 500 600
-10
-5
0
5
CD
/ m
deg
Wavelength / nm
273 K 268 K 263 K
300 400 500-30
-15
0
15
30
Wavelength/nm
CD
/mde
g
298 K 293 K 288 K 283 K 278 K 273 K 268 K 263 K
a) b)
300 400 500 600
-10
-5
0
5
CD
/ m
deg
Wavelength / nm
273 K 268 K 263 K
300 400 500-30
-15
0
15
30
Wavelength/nm
CD
/mde
g
298 K 293 K 288 K 283 K 278 K 273 K 268 K 263 K
a) b)
Fig. S3 Temperature dependent CD spectra of a) A-OPV3UT and b) A-OPV4T in S-citronellol at an interval of 5 K when cooled from molecularly dissolved state (2 x 10-4 M, dT/dt = -60 K/hr).
.
300 400 500 6000.0
0.5
1.0
1.5
2.0
273 K - 263 K
273 K373 K
Abs
orba
nce
Wavelength/nm
a) b) c)
300 400 500 6000.0
0.5
1.0
1.5
2.0
273 K - 263 K
273 K373 K
Abs
orba
nce
Wavelength/nm
a) b) c)
Fig S4. (a) Temperature dependent absorption spectra of A-OPV4T (2 x 10-4 M) in S-citronellol; (b) and (c) AFM images of the self-assembled fibers of A-OPV4T from S-citronellol.
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2011
Fig S5. CD (top) and absorption (bottom) cooling curves of AOPV4T in S-2,6-dimethyl octane. The cooling curves are obtained by monitoring the CD intensity at 470 nm (2 x 10-4 M, dT/dt = -60 K/hr).
Supplementary Material (ESI) for Chemical CommunicationsThis journal is (c) The Royal Society of Chemistry 2011
