10.1002/asia.201701061
Chemistry - An Asian Journal
FULL PAPER
(t, J = 7.4 Hz, 8H), 1.40 (m, J = 7.4 Hz, 8H), 1.13 (m, J = 7.4 Hz, 8H),
0.84 (t, J = 7.2 Hz, 12H); 13C NMR (100 MHz, CDCl3, Me4Si) =140.36,
139.96, 139.58, 139.32, 137.50, 133.07, 131.12, 129.62, 126.84, 119.18,
35.00, 33.28, 21.77, 13.95; FT-IR (cm-1): 3019, 2925, 2857, 1902, 1633,
1514, 1489, 1384, 1069, 1010, 859, 832, 755; MS (MALDI-TOF): m/z
916.5406.
Acknowledgements
This work was financially supported by the National Natural
Science Foundation of China (21274027 and 20974022) and the
Innovation Program of Shanghai Municipal Education
Commission (15ZZ002).
Compound 3a: 5.34 g (14.6 mmol) of 2,7-dibromophenanthrene-9,10-
dione and 1,3-diphenylpropan-2-one (3.7 g 17.6 mmol) were added to 40
mL methanol under stirring. This mixture was refluxed, and then a 50 mL
solution of 0.3 M KOH (15.0 mmol) in methanol was added dropwise.
Then the reaction system vigorously stirred at 80 C. After stirring for 2.5
h, the reaction was stopped and filtered to get the product. A dark green
solid was obtained and washed with methanol. The substance was dried
under reduced pressure to obtain 4.5 g of 3a at 54% yield without other
purification. 1H NMR (400 MHz, CD2Cl2, Me4Si) =6.96 (d, J = 8.4 Hz,
4H), 6.72-6.69 (m, 20H), 2.39 (t, J = 7.4 Hz, 8H), 1.40 (m, J = 7.4 Hz, 8H),
1.13 (m, J = 7.4 Hz, 8H), 0.84 (t, J = 7.2 Hz, 12H); 13C NMR (100 MHz,
CDCl3, Me4Si) =140.36, 139.96, 139.58, 139.32, 137.50, 133.07, 131.12,
129.62, 126.84, 119.18, 35.00, 33.28, 21.77, 13.95; FT-IR (cm-1): 3019,
2925, 2857, 1902, 1633, 1514, 1489, 1384, 1069, 1010, 859, 832, 755;
MS (MALDI-TOF): m/z 916.5406.
The authors thank beamline BL14B1 (Shanghai Synchrotron
Radiation Facility) for providing the beam time and helps during
experiments.
Keywords: low bandgap materials • conjugated polymers •
polycyclic aromatic hydrocarbons • luminescent materials •
organic field-effect transistors
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