Journal of Materials Chemistry C
Paper
Synthesis of T-NT-T, F-NT-F, T-BT-T and F-BT-F
Acknowledgements
Compounds 5–8 (130 mg, 0.30 mmol), 5-hexyl-2-thiophene
boronic acid pinacol ester (225 mg, 0.76 mmol), Pd(PPh3)4
(20 mg, 0.02 mmol), and 2 M Na2CO3 (5.4 mL) were added into
a 100 mL round-bottom flask. THF (15 mL) was added as a
solvent and then the mixture was stirred and degassed with N2
for 5 min. The mixture was stirred at reflux under N2 for 24 h.
After cooling, the mixture was extracted with dichloromethane
(70 mL ꢁ 2). The combined organic phase was washed with
water (70 mL) and brine solution (70 mL), dried over anhydrous
Na2SO4, filtered and evaporated to dryness. To obtain a product
of higher purity, the residue was further purified by silica
column chromatography eluting with the mixture of dichloro-
methane and hexane (1 : 3) followed by recrystallisation from
the mixed solvent of dichloromethane and methanol.
This research work was financially supported by the Thailand
Research Fund (RTA6080005); the Grant-in-Aid for Scientific
Research (A) (No. 19H00891) from the Japan Society for the
Promotion of Science (JSPS); and the National Nanotechnology
Center, National Science and Technology Development Agency,
Ministry of Higher Education, Science, Research and Innovation,
Thailand, through its program of Research Network National
Nanotechnology Center. Part of this work was conducted at the
Equipment Development Center (Institute for Molecular Science)
supported by the Nanotechnology Platform Program of the
Ministry of Education, Culture, Sport, Science and Technology
(MEXT), Japan. Thanks also go to Vidyasirimedhi Institute of
Science and Technology for the support of both the PhD research
grant and equipment.
1
F-BT-F. Dark pink solids (87%). H NMR (600 MHz, CDCl3)
d ppm: 8.07 (s, 2H), 7.72 (s, 2H), 7.21 (s, 2H), 6.76 (d, J = 3.36,
2H), 6.64 (d, J = 2.46 Hz, 2H), 2.84 (s, 4H), 1.72 (m, 4H), 1.41 (m, References
4H), 1.33 (m, 8H), 0.90 (t, J = 6.72, 6H); 13C NMR (151 MHz,
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121.09, 114.62, 107.45, 31.62, 31.67, 30.25, 28.84, 22.65, 14.15;
HRMS MALDI-TOF m/z [M]+: calcd for C36H36N2O2S3 600.1939;
found 600.4812.
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T-BT-T. Dark red solids (84%). 1H NMR (600 MHz, CDCl3)
d ppm: 8.03 (d, J = 3.78 Hz, 2H), 7.80 (s, 2H), 7.18 (d, J = 3.84 Hz,
2H), 7.10 (d, J = 3.42 Hz, 2H), 6.72 (d, J = 3.48 Hz, 2H), 2.81
(t, J = 7.56 Hz, 4H), 1.70 (m, 4H), 1.40 (m, 4H), 1.33 (m, 8H), 0.90
(t, J = 6.90 Hz, 6H); 13C NMR (151 MHz, CDCl3) d 152.53, 146.07,
139.41, 137.46, 134.65, 128.27, 125.53, 125.10, 124.97, 123.83,
123.79, 31.58, 30.25, 28.78, 22.58, 14.06; HRMS MALDI-TOF m/z
[M]+: calcd for C34H36N2S5 632.1482; found 632.4111.
F-NT-F. Dark blue solids (65%). 1H NMR (600 MHz,
CD3COCD3) d ppm: 8.90 (dd, J = 7.02 Hz, 3.12 Hz, 2H), 7.65
(d, J = 3.36, 2H), 7.60 (dd, J = 7.14 Hz, 3.06 Hz, 2H), 7.34
(d, J = 3.42 Hz, 2H), 6.96 (d, J = 3.36 Hz, 2H), 6.89 (d, J = 3.18 Hz,
2H), 2.88 (t, J = 7.44 Hz, 4H), 1.73 (m, 4H), 1.44 (s, 4H), 1.34
(t, J = 3.36 Hz, 8H), 0.89 (t, J = 6.66 Hz, 6H); 13C NMR (151 MHz,
CD3COCD3) d 150.71, 150.25, 149.01, 146.08, 130.86, 130.65,
127.40, 127.19, 125.42, 124.96, 123.45, 122.62, 118.37, 106.98,
31.52, 31.46, 31.36, 22.32, 13.39; HRMS MALDI-TOF m/z [M]+:
calcd for C38H38N2O2S3 650.2095; found 650.5062.
T-NT-T. Purple solids (66%). 1H NMR (600 MHz, CDCl3)
d ppm: 8.44 (dd, J = 6.72 Hz, 2.88 Hz, 2H), 7.45 (dd, J = 6.90 Hz,
2.82 Hz, 2H), 7.39 (d, J = 2.40 Hz, 2H), 7.31 (d, J = 3.36 Hz, 2H),
7.11 (d, J = 2.46 Hz, 2H), 6.73 (d, J = 2.46 Hz, 2H), 2.83 (t, J =
7.32 Hz, 4H), 1.71 (m, 4H), 1.41 (s, 4H), 1.33 (t, J = 3.42, 8H),
0.90 (t, J = 6.30 Hz, 6H); 13C NMR (151 MHz, CDCl3) d 151.50,
146.03, 140.81, 134.64, 134.39, 132.84, 131.37, 127.09, 127.03,
124.91, 123.88, 123.19, 123.14, 31.58, 31.56, 30.25, 28.76, 22.58,
14.08; HRMS MALDI-TOF m/z [M]+: calcd for C38H38N2S5
682.1639; found 682.4468.
Conflicts of interest
There are no conflicts to declare.
J. Mater. Chem. C
This journal is © The Royal Society of Chemistry 2020