36
2 Biphenyl Moiety for a Solvent Responsive Aryl Gold(I) …
were recorded on a Photonic Hamamatsu PMA-12 Multichannel Analyzer. The emission quantum yields of the solid samples were recorded on a Hamamatsu QuantaurusQY spectrometer with an integrating sphere. Emission lifetime measurements were
recorded on a Hamamatsu Quantaurus-Tau spectrometer. Elemental analyses and
low- and high resolution mass spectra were recorded at the Global Faculty Center at Hokkaido University. Photographs were obtained using Olympus BX51 or
SZX7 microscopes with Olympus DP72, Nikon D5100 digital cameras. Thermal
gravimetric analysis profiles were recorded on Bruker TG-DTA2010SAT.
2.7.2 Synthesis
Synthesis of 5
CN
NC
CH 2 Cl 2
Cl Au S
r.t., 3 h
Cl Au C N
N C Au Cl
5
6
2,2
-Diisocyano-1,1
-biphenyl 6 (0.610 g, 3.0 mmol) [22] and
chloro(tetrahydrothiophene)gold(I) (1.930 g, 6.0 mmol) were dissolved in CH 2 Cl 2
(30 mL) and stirred for 3 h. The solvent was removed with a rotary evaporator under
a reduced pressure. Washing with methanol gave an analytically pure white solid
5 (1.776 g, 2.7 mmol, 88%).
1 H NMR (400 MHz, CDCl 3 , δ): 7.50–7.53 (m, 2H),
7.67–7.53 (m, 2H), 7.76–7.80 (m, 4H). MS-ESI (m/z): [M + Na]
+ calculated for
C 26 H 18 Au 2 N 2 Na, 690.9293; found, 690.9293. Anal. Calcd for C 26 H 18 Au 2 N 2 : C,
25.13; H, 1.21; N, 4.19. Found: C, 25.18; H, 1.06; N, 4.04. This compound exhibits
poor solubility in common organic solvents (for example, maximum solubility in
CHCl 3 is 2 mg/mL); therefore,
13 C NMR spectroscopy cannot be measured.
Synthesis of 3
ZnI-LiCl +
Cl Au C N
N C Au Cl
Au C N
N C Au
0 °C, 2 h
THF
5
3
4