McKinlay et al. 10.1073/pnas.0408113102.

Supporting Information

Files in this Data Supplement:

Supporting Figure 7
Supporting Figure 8
Supporting Table 1
Supporting Table 2
Supporting Text




Supporting Figure 7

Fig. 7. (+)-MALDI-TOF MS of 2.





Supporting Figure 8

Fig. 8. (–)-MALDI-TOF MS of 2.





 

Table 1. (+)-MALDI-TOF MS analysis of 2

m/z found

m/z calculated

Fragment

[Cu24(C40H40O16)6 + E + H]+*

6,473.48

6,473.14

[Cu24C252H271O103]+

4 acetone + 3 water

6,595.51

6,595.21

[Cu24C249H285O112]+

3 acetone + 13 water

6,656.87

6,657.26

[Cu24C255H291O111]+

5 acetone + 10 water

6,714.99

6,715.30

[Cu24C258H297O112]+

6 acetone + 10 water

6,677.68

6,677.24

[Cu24C243H295O121]+

1 acetone + 24 water

6,735.59

6,735.28

[Cu24C246H301O122]+

2 acetone + 24 water

*E, encapsulated guests.





Table 2. (–)-MALDI-TOF MS analysis of 2

m/z found

m/z calculated

Fragment

[Cu24(C40H40O16)6 + E – H]–*

6,604.80

6,605.23

[Cu24C258H283O106]–

6 acetone + 4 water

6,665.00

6,665.23

[Cu24C249H291O116]–

3 acetone + 17 water

6,731.11

6,731.30

[Cu24C258H297O113]–

6 acetone + 11 water

6,779.84

6,779.28

[Cu24C240H305O129]–

0 acetone + 33 water

6,848.78

6,849.35

[Cu24C252H311O124]–

4 acetone + 24 water

*E, encapsulated guests.





Supporting Text

Synthesis and Characterization. All materials (Aldrich) were used as supplied. All 1H and 13C NMR spectra were recorded on a Bruker DRX300 (300 and 75 MHz, respectively) at 300 K and referenced to internal tetramethylsilane standard.

C-propan-3-ol pyrogallol[4]arene 1. First, 2,3-dihydrofuran (100 g, 1.43 mol) was added dropwise over a period of 6 h to pyrogallol (179.9 g, 1.43 mol), conc. HCl (35 ml), and methanol (600 ml) under an atmosphere of N2 gas. The resulting mixture was refluxed for 6 days, filtered, washed with water (3 × 500 ml), and recrystallized from methanol. C-propan-3-ol pyrogallol[4]arene 1 (152 g, 54%) was collected as colorless powder. 1H NMR (DMSO) d : 1.34 (8H, t, 3J = 6.6 Hz), 2.18 (8H, m), 3.42 (8H, t, 3J = 6.6 Hz), 4.15 (4H, t, 3J = 7.7 Hz), 4.31 (4OH, bs), 6.88 (4H, s), 8.46 (12OH, bs); 13C NMR (DMSO) d : 29.56, 31.08, 31.63, 33.92, 61.05, 113.85, 124.83, 133.2, 140.00. (+)-ESI-MS (MeOH): m/z = 807.36, calc. for [M + Na]+ 807.28; m/z = 1,591.88, calc. for [2M + Na]+ 1591.90; m/z = 1592.64, calc. for [6M + 3Na]3+ 1,592.24. Isotope pattern was more consistent with [6M + 3Na]3+ compared with [4M + 2Na]2+. Anal. calc. for C40H48O16× H2O: C, 59.84%; H, 6.28%. Found: C, 59.22%, H, 6.58%.