Nesting Complexation of C 60 with Large, Rigid D 2 Symmetrical Macrocycles
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1 Supporting Information for: Nesting Complexation of C 60 with Large, Rigid D 2 Symmetrical Macrocycles Marco Caricato, a Carmine Coluccini, a Daniele Dondi, b Douglas Vander Griend, c and Dario Pasini, *a a) Department of Organic Chemistry, University of Pavia, Viale Taramelli, Pavia, Italy. Fax: ; Tel: ; dario.pasini@unipv.it b) Department of General Chemistry, University of Pavia, Viale Taramelli Pavia, Italy. c) Department of Chemistry & Biochemistry, Calvin College, Grand Rapids MI USA. Contents: Additional NMR and UV/Vis spectra (pages S2-S10) Minimized conformation of macrocycles (page S11) Copies of 1 H NMR, 13 C NMR and mass spectra (pages S12-S28) Additional details on calculations (page S29-S48) 1
2 Figure S1. 1 H NMR spectra (CDCl 3, 300 MHz, room temperature) of macrocycles a) (RR)-8; b) (RR)-9; c) (RR)-10; d) (RR)-11. 2
3 Table S1. Selected 1 H NMR chemical shifts for precursors (R)-4-7 and macrocycles (RR)-8-11, in CDCl 3 at room temperature. [a] Ha X O Ar O Compound BINOL-OMe (s) [b] BINOL-Ha (s) [b] Ar-CH 2 O Binol-CH 2 O (R)-1 [c] (dd) (R) (s) 4.91(dd) (R) (dd) (R) (s) 4.98(dd) (R) (dd) (RR) (m) (m) (RR) (dd) (RR) (m) (m) (RR) (dd) [a] Spectra taken at 300 MHz with 5-10 mm sample concentration in CDCl 3. [b] Peak multiplicity as follows: s singlet, bs broad singlet, d doublet, m multiplet, dd double doublet (AB system). [c] Data taken from reference 9. 3
4 Figure S2. Normalized UV/Vis spectra of macrocycles (RR)-8-11 (6 x x 10-5 in EtOH). 1e+5 ε (M -1 cm -1 ) (RR)-9 (RR)-8 (RR)-11 (RR) λ (nm) For UV/Vis of molecular fragments of the macrocycles (taken from literature): a) 4,4 -dimethylbiphenyl: λ max =254 nm (ε=18400 in petroleum ether) S1 b) 4,4 -dicarboxy dimehtyl ester: λ max =280 nm (ε=30000 in EtOH) S2 c) 1,4-bis(4-carbomethoxyphenyl)buta-1,3-diyne (MeCN): λ max (ε x 10-4 ) = 284 (0.50), 302 (0.58), 322 (0.78), 345 (0.68). S3 d) 1,4-bis(phenylethynyl)buta-1,3-diyne (MeCN): λ max (ε x 10-4 ) = 296 (2.16), 305 (3.62), 326 (3.50). S3 4
5 Figure S3. Titration of C 60 (65 μm) with macrocycle (RR)-8 (0-485 μm) in toluene at 25 C. 0,3 A 0, λ (nm) 5
6 Figure S4. Titration of C 60 (103 μm) with macrocycle (RR)-9 (0-500 μm) in toluene at 25 C. 1,0 A 0,5 0, λ (nm) 6
7 Figure S5. Calculated curves for the 1:1 complexes between macrocycles (RR)-8, (RR)-9 and (RR)-11 in toluene at 25 C and related simulated macrocycle absorbance curves ε 3000 (RR)-11 (RR)-11@C60 (RR)-8 (RR)-8@C60 C60 (RR)-9 (RR)-9@C λ (nm) 7
8 Figure S6. Spectrophotometric Titration of 65 μm C 60 with Macrocycle (RR)-8. Summary: Data at 295 K Non-negativity was enforced with optimization (not truncation). DG1 = (±0.0114); RMS Residual = Unrestricted RMS Residual (3 mathematical factors): Restricted Data Reconstruction (3 chemical factors): % Unrestricted Data Reconstruction (3 mathematical factors): % Remaining Imbedded Error in Absorbance Values: R 2 : % 8
9 Figure S7. Spectrophotometric Titration of 103 μm C 60 with Macrocycle (RR)-9. Summary: Data at 298 K Non-negativity was enforced with optimization (not truncation). DG1 = (±0.0875); RMS Residual = Unrestricted RMS Residual (3 mathematical factors): Restricted Data Reconstruction (3 chemical factors): % Unrestricted Data Reconstruction (3 mathematical factors): % Remaining Error Imbedded in Absorbance Values: R²: % 9
10 Figure S8. Spectrophotometric Titration of 69 μm C 60 with Macrocycle (RR)-11. Summary: Data at 298 K Non-negativity was enforced with optimization (not truncation). DG1 = (±0.015); RMS Residual = Unrestricted RMS Residual (3 mathematical factors): Restricted Data Reconstruction (3 chemical factors): % Unrestricted Data Reconstruction (3 mathematical factors): % Remaining Imbedded Error in Absorbance Values: R 2 : % 10
11 Supplementary Material (ESI) for Organic & Biomolecular Chemistry Figure S9. Minimized structures of macrocycles (RR)-8, (RR)-9, (RR)-10 and (RR)
12 Compound (R)-4. 1 H NMR (CDCl 3, 300 MHz) 13 C NMR (CDCl 3, 75 MHz) 12
13 13 C NMR DEPT (CDCl 3, 75 MHz) ESI MS 13
14 Compound (R)-5. 1 H NMR (CDCl 3, 300 MHz) 13 C NMR (CDCl 3, 75 MHz) 14
15 13 C NMR DEPT (CDCl 3, 75 MHz) 15
16 Compound (R)-6. 1 H NMR (CDCl 3, 300 MHz) 13 C NMR (CDCl 3, 75 MHz) 16
17 13 C NMR DEPT (CDCl 3, 75 MHz) 17
18 Compound (R)-7. 1 H NMR (CDCl 3, 300 MHz) 13 C NMR (CDCl 3, 75 MHz) 18
19 13 C NMR DEPT (CDCl 3, 75 MHz) 19
20 Macrocycle (RR) C NMR (CDCl 3, 75 MHz) 13 C NMR DEPT (CDCl 3, 75 MHz) 20
21 ESI mass spectrum 21
22 Macrocycle (RR) C NMR (CDCl 3, 75 MHz) 13 C NMR DEPT (CDCl 3, 75 MHz) 22
23 ESI mass spectrum 23
24 Macrocycle (RR) C NMR (CDCl 3, 75 MHz) 13 C NMR DEPT (CDCl 3, 75 MHz) 24
25 ESI mass spectrum 25
26 Macrocycle (RR) C NMR (CDCl 3, 75 MHz) 13 C NMR DEPT (CDCl 3, 75 MHz) 26
27 ESI mass spectrum 27
28 Details on calculations. Optimizations were carried out at the PM3 level of theory as implemented by the Gaussian 2003 package. S4 Atomic Coordinates and Energies for the reported molecules Below are listed coordinates in cartesian format (units are in Ǻ) and energies (in parentheses, units are in Hartrees) for the most stable conformers of the reported molecules. The calculated energy for C 60, used in this paper, was Ha. (RR)-8 ( Ha) C C C C C C H H C C H H C C H C C C C C C C H C C C H H H H O O C H C H H H C H O C C C C H C H
29 C H H H C C O C C C C C C H C H C H H C H H C H H H C H H H C C C C C C C C C O C C C O C H C C C C C H C C C C C H H H H H O
30 H H H C H H H H H O H H H H C H H H C C C C H C H C H H C C C C C C C C H C H C H H C H H (RR)-9 ( ) C C C C C C H H C C H H C C H
31 C C C C C C C H C C C H H H H O O C H C H H C O C C C C H C H C H H H C C O C C C C C C H C H C H H C C H H H C H H H C C C C
32 C C C C C O C C C O C H C C C C C H C C C C C H H H H H O H H H C H H H H H O H H H H C H C C C C H C H C H H C C C C C C C C
33 H C H C H H C O O O O (RR)-10 ( ) C C C C C C C C C C C C C C C C C C C C O O C C O C C C C C C C C C C C C C C O C C O C C C C C C C
34 C C C C C O C C C C C C O C C C C C C C C C C C O C C C C C C C C C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H
35 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H (RR)-11 ( ) C C C C C C C C C C C C C C C C C C C C O O C C O C
36 C C C C C C C C C C C C C O C C O C C C C C C C C C C C C O C C C C C C O C C C C C C C C C C C O C C C C C O O O O C C C C H
37 H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H C 60 :(RR)-8 ( ) C C C C C C
38 H H C C H H C C H C C C C C C C H C C C H H H H O O C H C H H H C H O C C C C H C H C H H H C C O C C C C C C H C H C H H C H
39 H C H H H C H H H C C C C C C C C C O C C C O C H C C C C C H C C C C C H H H H H O H H H C H H H H H O H H H H C H H H C C C
40 C H C H C H H C C C C C C C C H C H C H H C H H C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C
41 C C C C C C C C C C C C C C C C C C C C C C 60 :(RR)-9 ( ) C C C C C C H H C C H H C C H C C C C C C C H C C C H H H H O O C H C H H C O C
42 C C C H C H C H H H C C O C C C C C C H C H C H H C C H H H C H H H C C C C C C C C C O C C C O C H C C C C C H C C C C C H H
43 H H H O H H H C H H H H H O H H H H C H C C C C H C H C H H C C C C C C C C H C H C H H C C C C C C C C C C C C C C C C C C C
44 C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C O O O O C 60 :(RR)-11 ( ) C C C C C C C C C C C C C C C
45 C C C C C O O C C O C C C C C C C C C C C C C C O C C O C C C C C C C C C C C C O C C C C C C O C C C C C C C C C C C O C C C
46 C C O O O O C C C C H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H
47 H H H C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C
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