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(400 MHz, DMSO-d6) d (ppm): 8.47 (dd, J ¼ 6.0, 8.4 Hz, 2H), 8.40 (East China University of Science & Technology) for his kind
(d, J ¼ 8.1 Hz, 1H), 7.81 (t, J ¼ 8.2 Hz, 1H), 7.33 (d, J ¼ 8.2 Hz, help.
1H), 4.59 (bar, 1H), 4.23 (t, J ¼ 6.6 Hz, 2H), 3.64 (t, J ¼ 6.5 Hz,
2H), 3.46 (bar, 4H), 3.22–3.16 (m, 4H), 3.07 (t, J ¼ 4.5 Hz, 4H).
Notes and references
M4-S2 was obtained by the same procedure with M3-S2
instead of M3-S1 (71.5%). 1H-NMR (400 MHz, DMSO-d6) d
(ppm): 8.47 (dd, J ¼ 2.6, 7.2 Hz, 2H), 8.40 (d, J ¼ 8.1 Hz, 1H), 7.81
(t, J ¼ 7.4 Hz, 1H), 7.34 (d, J ¼ 8.1 Hz, 1H), 4.03 (t, J ¼ 7.3 Hz,
2H), 3.20 (t, J ¼ 4.7 Hz, 4H), 3.10 (t, J ¼ 4.7 Hz, 4H), 1.64–1.54 (m,
2H), 1.39–1.28 (m, 2H), 0.92 (t, J ¼ 7.3 Hz, 3H).
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´
Synthesis of PET-S1 and PET-S2. 175 mg of M4-S1 (0.47
mmol) and 189 mg of compound M2 (0.64 mmol) were added
into 40 mL mixed solution of THF–CH3OH (V : V ¼ 1 : 1). The
above solution was heated to reux under N2 atmosphere.
Then 2 mL of triethylamine was added dropwise to the
above solution. Aer the raw material exhausted, the solvent
was removed under reduced pressure to afford crude
product, which was puried by column chromatography
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[CH2Cl2 : CH3OH
¼
200 : 1–4 : 1 (V : V) containing 1%
triethylamine] to give yellow oil. Then 20% HCl was added
into the oil and the mixed solution was stirred overnight
under room temperature. The resulted solution was poured
into 100 mL deionized water and its pH was adjusted to
ꢀ7 with NaOH to yield yellow precipitation. The solution was
ltered to obtain probe PET-S1 as yellow solid (47 mg,
1
20.0%). H-NMR (400 MHz, DMSO-d6) d (ppm): 9.08 (s, 2H),
8.46 (t, J ¼ 7.7 Hz, 2H), 8.39 (d, J ¼ 8.1 Hz, 1H), 7.81 (t, J ¼ 7.7
Hz, 1H), 7.69 (d, J ¼ 6.7 Hz, 1H), 7.35 (d, J ¼ 7.9 Hz, 1H), 7.29
(t, J ¼ 6.3 Hz, 2H), 7.25–7.19 (m, 1H), 4.66–4.60 (m, 1H), 4.22
(t, J ¼ 6.4 Hz, 2H), 3.73 (s, 2H), 3.63 (t, J ¼ 6.5 Hz, 2H), 3.46 (t,
J ¼ 4.6 Hz, 4H), 3.26 (bar, 4H), 2.77 (bar, 4H). 13C-NMR (400
MHz, DMSO-d6): 163.55, 163.01, 155.33, 141.07, 135.02,
132.21, 130.71, 130.54, 129.92, 129.13, 129.08, 126.84, 126.15,
125.28, 122.47, 115.67, 115.17, 72.05, 66.90, 62.77, 60.11,
52.07, 51.59, 38.56. HR-MS observed m/z: 504.2306 (M + H)+,
518.2462 (M
27H31BN3O6: 504.2306 for (M + H)+, C28H33BN3O6: 518.2462
for (M + CH3)+.
+
CH3)+; calculated molecular weight of
C
PET-S2 was obtained by the same procedure with M4-S2
instead of M4-S1 (35.0%). 1H-NMR (400 MHz, CDCl3) d
(ppm): 8.93 (bar, 2H), 8.58 (d, J ¼ 7.2 Hz, 1H), 8.50 (d, J ¼ 8.0
Hz, 1H), 8.37 (d, J ¼ 8.4 Hz, 1H), 7.98 (d, J ¼ 8.5 Hz, 1H), 7.69
(t, J ¼ 7.5 Hz, 1H), 7.42–7.35 (m, 2H), 7.26–7.20 (m, 2H), 4.16
(t, J ¼ 7.5 Hz, 2H), 3.81 (s, 2H), 3.31 (bar, 4H), 2.88 (bar, 4H),
1.75–1.66 (m, 2H), 1.50–1.38 (m, 2H), 0.97 (t, J ¼ 7.3 Hz, 3H).
13C-NMR (400 MHz, CDCl3): 164.42, 163.96, 155.14, 140.32,
136.54, 132.43, 131.14, 130.78, 130.33, 129.84, 129.78,
127.80, 126.19, 125.90, 123.38, 117.37, 115.28, 52.42, 52.07,
64.20, 40.12, 30.24, 20.39, 13.86. HR-MS observed m/z:
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472.2409 (M
27H31BN3O4: 472.2408 for (M + H)+.
+
H)+, calculated molecular weight of
C
Acknowledgements
This work was nancially supported by National 973 Program
(no. 2011CB910403), NSFC (no. 21235005) and Shanghai
Municipal Natural Science Foundation. We thank Dr H.-Y. Tian
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2842 | RSC Adv., 2015, 5, 2837–2843
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