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groups were observed during the ringꢀclosing reaction. Hence, we
attempted other conditions to achieve ringꢀclosing using 2.Te and 3
without the need for heating, such as using sodium hydride as base in
THF. It is notable that successful ringꢀclosing was only observed
using the presently reported conditions of Cs2CO3 in DMF with heatꢀ
ing.
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(61) Analogous 1H NMR titrations in d6ꢀacetone showed no evꢀ
idence of chloride binding for neutral macrocycle 1.Se. Due to soluꢀ
bility issues, chloride titrations with 1.Te could only be performed in
CD2Cl2 and d6ꢀDMSO, which revealed no perturbations of any proton
environments in either solvent.
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(66) Single crystal Xꢀray diffraction data for 10.SeꢀI were colꢀ
lected with synchrotron radiation using I19ꢀ1 at Diamond Light
Source (λ = 0.6889 Å).[REF2] Cell parameters were determined and
refined and raw frame data were integrated using CrysAlisPro. The
structure was solved with SuperFlip [REF3] and refined by fullꢀ
matrix least squares on F2 using CRYSTALS [REF4]. Single Crystal
Data: C36H44I2N6O6Se2, I2, 0.928(C2H3N), Mr = 4415.49, monoclinic,
P21/c= 22.6944(7) Å, b = 21.4972(5) Å,
c
=
9.4414(3) Å,
β = 99.847(3)°, = 4538.3(2) Å, data/restraints/parameters:
V
9208/1878/716, Rint = 11.4%, final R1 = 6.83%, wR2 = 17.67%
(I>2σ(I)), ꢁρmin,max = ꢀ1.34,+2.66 e.Å3. Crystallographic data (excludꢀ
ing structure factors) have been deposited with the Cambridge Crysꢀ
tallographic Data Centre (CCDC 1521870) and copies of these data
(44) Winn, J.; Pinczewska, A.; Goldup, S. M. J. Am. Chem.
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(45) Berná, J.; Crowley, J. D.; Goldup, S. M.; Hänni, K. D.;
Lee, A.ꢀL.; Leigh, D. A. Angew. Chem. Int. Ed. 2007, 46 (30), 5709–
5713.
(46) Goldup, S. M.; Leigh, D. A.; Lusby, P. J.; McBurney, R.
T.; Slawin, A. M. Z. Angew. Chem. Int. Ed. 2008, 47 (18), 3381–
3384.
(47) Goldup, S. M.; Leigh, D. A.; McBurney, R. T.;
McGonigal, P. R.; Plant, A. Chem Sci 2010, 1 (3), 383–386.
can
be
obtained
free
of
charge
via
www.
ccdc.cam.ac.uk/data_request/cif.
(67) More competitive solvents containing greater quantities of
water could not be used for anion titrations using macrocycle 10.Se,
as the perturbations of the various proton environments were too
small for reliable values of association constants to be determined.
1
(68) Unless otherwise stated in Table 2, the H NMR titrations
show all anions investigated associate with the cationic host moleꢀ
cules in a 1:1 stoichiometry, with no evidence of a second anion bindꢀ
ing event.
12
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