140
5 Mechanical-Stimulation-Triggered and Solvent-Vapor-Induced …
chromatography (SiO 2 , volume ratio of CH 2 Cl 2 /Hexane = 1:1) gave a yellow solid.
The resulting solid was dried under reduced pressure to give 3 (0.129 g, 0.25 mmol,
80%).
1 H NMR (400 MHz, CDCl 3 , δ): 7.23–7.25 (m, 2H), 7.40–7.70 (m, 11H),
7.96–8.00 (m, 2H).
13 C NMR (400 MHz, CDCl 3 , δ): 121.0 (C), 122.3 (CH), 123.9
(C), 124.5 (C), 124.7 (CH), 125.3 (CH), 126.4 (CH), 127.5 (CH), 128.5 (C), 128.8
(CH), 128.9 (CH), 129.1 (C), 129.3 (C), 129.6 (CH), 130.1 (CH), 132.2 (CH), 133.6
(C), 133.8 (CH), 136.3 (CH), 138.8 (CH), 143.4 (CH), 162.1 (C), 163.2 (C). MS-EI
(m/z): [M+H]
+ calcd for C 24 H 15 AuNF 3 , 571.08221; found, 571.07198. Anal. Calcd
for C 24 H 15 AuNF 3 : C, 50.45; H, 2.65; N, 2.45. Found: C, 50.04; H, 2.45; N, 2.36.
5.7.3 Preparation of Crystals of 3G/MeOH and 3O
Preparation of 3G/MeOH: The crystallization of 3G/MeOH was accomplished by
layering MeOH on a solution of 3 in CH 2 Cl 2 at 2 °C for ~3 days (typically, such solutions contained 10 mg of the complex in 5 mL of CH 2 Cl 2 ) which afforded 3G/MeOH
crystals that exhibited green emission under UV irradiation (365 nm; Fig. 5.6a). Crystals of 3G/MeOH did not show a change of emission when being placed in a petri
dish (radius: 9 cm) that contained paper wipes (Kimwipes) impregnated with MeOH
at 22 °C (~75 mL; Fig. 5.6c). (b) Crystals of 3G/MeOH showed an emission change
from green to orange (3O scsc ; Fig. 5.6b) when being exposed to ambient conditions.
Preparation of crystals of 3O: The crystallization of 3O was accomplished by a
procedure similar to that used for the preparation of 3G/MeOH, albeit that hexane
was used instead of MeOH. Crystals of 3O (size: ~1 mm) exhibit orange emission
under irradiation with UV light (365 nm).
Fig. 5.6 Photographs of a a crystal of 3G/MeOH in the petri dish containing MeOH vapor and
b an orange-emitting crystal obtained after exposing the 3G/MeOH crystal to ambient conditions.
c A petri dish containing paper wipes (Kimwipes) impregnated with MeOH. Photographs in a and
b were taken under irradiation with UV light (365 nm), while the photograph in c was taken under
illumination with ambient light
5 Mechanical-Stimulation-Triggered and Solvent-Vapor-Induced …
chromatography (SiO 2 , volume ratio of CH 2 Cl 2 /Hexane = 1:1) gave a yellow solid.
The resulting solid was dried under reduced pressure to give 3 (0.129 g, 0.25 mmol,
80%).
1 H NMR (400 MHz, CDCl 3 , δ): 7.23–7.25 (m, 2H), 7.40–7.70 (m, 11H),
7.96–8.00 (m, 2H).
13 C NMR (400 MHz, CDCl 3 , δ): 121.0 (C), 122.3 (CH), 123.9
(C), 124.5 (C), 124.7 (CH), 125.3 (CH), 126.4 (CH), 127.5 (CH), 128.5 (C), 128.8
(CH), 128.9 (CH), 129.1 (C), 129.3 (C), 129.6 (CH), 130.1 (CH), 132.2 (CH), 133.6
(C), 133.8 (CH), 136.3 (CH), 138.8 (CH), 143.4 (CH), 162.1 (C), 163.2 (C). MS-EI
(m/z): [M+H]
+ calcd for C 24 H 15 AuNF 3 , 571.08221; found, 571.07198. Anal. Calcd
for C 24 H 15 AuNF 3 : C, 50.45; H, 2.65; N, 2.45. Found: C, 50.04; H, 2.45; N, 2.36.
5.7.3 Preparation of Crystals of 3G/MeOH and 3O
Preparation of 3G/MeOH: The crystallization of 3G/MeOH was accomplished by
layering MeOH on a solution of 3 in CH 2 Cl 2 at 2 °C for ~3 days (typically, such solutions contained 10 mg of the complex in 5 mL of CH 2 Cl 2 ) which afforded 3G/MeOH
crystals that exhibited green emission under UV irradiation (365 nm; Fig. 5.6a). Crystals of 3G/MeOH did not show a change of emission when being placed in a petri
dish (radius: 9 cm) that contained paper wipes (Kimwipes) impregnated with MeOH
at 22 °C (~75 mL; Fig. 5.6c). (b) Crystals of 3G/MeOH showed an emission change
from green to orange (3O scsc ; Fig. 5.6b) when being exposed to ambient conditions.
Preparation of crystals of 3O: The crystallization of 3O was accomplished by a
procedure similar to that used for the preparation of 3G/MeOH, albeit that hexane
was used instead of MeOH. Crystals of 3O (size: ~1 mm) exhibit orange emission
under irradiation with UV light (365 nm).
Fig. 5.6 Photographs of a a crystal of 3G/MeOH in the petri dish containing MeOH vapor and
b an orange-emitting crystal obtained after exposing the 3G/MeOH crystal to ambient conditions.
c A petri dish containing paper wipes (Kimwipes) impregnated with MeOH. Photographs in a and
b were taken under irradiation with UV light (365 nm), while the photograph in c was taken under
illumination with ambient light