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(15) In our previous studies, we utilized an analogue of 1 providing
two methoxyethoxy groups on the m-phenylene rings. To increase the
solubility of the host−guest complexes in acetonitrile, we prepared
new ligand 1 bearing three methoxyethoxy groups.
(16) To the best of our knowledge, the use of Ag(I) ions as
photoresponsive hinges for coordination hosts has not been previously
reported. For mechanistic studies of the photoreduction of Ag(I) ions,
see: (a) Doigon, P.; Davis, T. W. J. Phys. Chem. 1952, 56, 764.
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(17) See the Supporting Information.
(18) The solubility of C60 in MeCN is extremely low (< 0.0013
mM): Ruoff, R. S.; Tse, D. S.; Malhotra, R.; Lorents, D. C. J. Phys.
Chem. 1993, 97, 3379−3383.
(19) The entire structures of C60 and the 2′⊃C60 complex were
optimized at the LC-BOP+LRD/6-31G* level in the gas phase, where
the molecular-mechanics-optimized structure was employed as the
initial structure for 2′⊃C60. The ECP28MDF pseudopotential was
used for silver atoms throughout the present study. Excitation energies
and oscillator strengths of the optimized structures were calculated by
time-dependent DFT using the LC-BOP functional. The same basis
set as in the geometry optimization was used for C60. For 2′⊃C60, the
6-31G basis set was used for atoms other than Ag. No symmetry was
imposed in the calculations. The numbers of excited states calculated
were 50 and 24 for C60 and 2′⊃C60, respectively. The GAMESS
program package was used for all of these quantum-chemical
calculations.
D
dx.doi.org/10.1021/ja406893y | J. Am. Chem. Soc. XXXX, XXX, XXX−XXX