1
(72%). H NMR (400 MHz, DMSO): (ppm) 8.44-8.42 (m, 2H), 8.04-8.01 (m, 4H), 7.77-7.68
(m, 4H), 5.62 (t, J = 5.93 Hz, 4H), 5.50 (t, J = 5.93 Hz, 4H), 4.59 (t, J = 7.52 Hz, 4H), 1.56 (q, J
13
= 7.57 Hz, 4H), 1.31 (sext, J = 7.61 Hz, 4H), 0.87 (t, J = 7.25 Hz, 6H); C NMR (100 MHz,
DMSO): (ppm) 142.96 (NCN), 135.10, 131.60, 130.90, 130.60, 126.92, 113.89, 113.71,
113.67, 49.96, 46.58, 44.95, 30.56, 19.01, 13.44; ESI-MS (positive mode): [C32H38N7Br2Hg]+
m/z = 882.1231 (observed), 882.1234 (calculated).
Synthesis of compound 9 Compound 5 (1.00 g, 2.42 mmol) was dissolved in 5 ml water and
ammonium hexaflorophosphate (0.43 g, 2.66 mmol) was added to it. An immediate precipitation
of compound 9 occurred, which was separated by filtration followed by washing with 2 ml
water. Yield: 1.16 g (94%). 1H NMR (400 MHz, CDCl3): (ppm) 8.52-8.50 (m, 2H), 8.07-8.05
13
(m, 2H), 5.59 (t, J = 5.40 Hz, 4H), 4.19 (t, J = 5.40 Hz, 4H); C NMR (100 MHz, CDCl3):
(ppm) 134.86, 131.57, 114.29, 52.87, 29.81; 19F NMR (100 MHz, CDCl3): (ppm) -73.05, -
74.58; 31P NMR (100 MHz, CDCl3): (ppm) -140.70 (sep), ESI-MS (positive mode):
[C10H12N3Br2]+ m/z = 333.9374 (observed), 333.9372 (calculated).
Synthesis of compound 10a Compound 9 (0.50 g, 1.04 mmol) was suspended in toluene and
pyrrolidine (0.19 g, 2.61 mmol) was added to it. Slowly compound 9 gets dissolved and the color
of the solution turns yellow. After stirring at rt for 24 h a light yellow precipitate of pure
1
compound 10a appeared, which was separated by filtration.Yield: 0.48 g (67%). H NMR (400
MHz, CDCl3): (ppm) 8.08-8.03 (m, 2H), 7.84-7.80 (m, 2H), 5.00 (t, J = 5.85 Hz, 4H), 3.18 (t, J
13
= 5.85 Hz, 4H), 2.53 (t, J = 3.16 Hz, 6H), 1.67 (t, J = 3.16 Hz, 4H); C NMR (100 MHz,
19
CDCl3): (ppm) 135.54, 131.91, 113.98, 54.27, 54.14, 51.62, 24.04; F NMR (100 MHz,
CDCl3): (ppm) -72.31, -72.82; 31P NMR (100 MHz, CDCl3): (ppm) -141.16 (sep), ESI-MS
(positive mode): [C18H28N5]+ m/z = 314.2339 (observed), 314.2339 (calculated).
Synthesis of compound 10b Compound 10b was prepared using the method similar to that used
for compound 10a. The reagents used were compound 9 (0.50 g, 1.04 mmol) and diethylamine
1
(0.12 g, 2.61 mmol). Yield: 0.23 g (53%). H NMR (400 MHz, CDCl3): (ppm) 8.29-8.28 (m,
13
2H), 8.09-8.08 (m, 2H), 5.41 (t, J = 5.85 Hz, 4H), 3.99 (t, J = 5.85 Hz, 4H), 2.94 (s, 12H); C
NMR (100 MHz, CDCl3): (ppm) 137.11, 133.60, 118.32, 114.63, 55.03, 48.05, 43.86; 19F
NMR (100 MHz, CDCl3): (ppm) -72.03, -73.54; 31P NMR (100 MHz, CDCl3): (ppm) -144.64
(sept), ESI-MS (positive mode): [C14H24N5]+ m/z = 262.2027 (observed), 262.2026 (calculated).