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137.1, 130.5, 137.1, 129.7, 128.3, 125.4, 121.3, 118.9, 115.7, 115.6,
105.8 ppm; FTIR (KBr): n˜ =3434 (vs), 3341 (vs), 3285 (vs), 2215 (m),
1793 (w), 1624 (m), 1605 (vs), 1521 (vs), 1447 (m), 1400 (m), 1281
(m), 1258 (s), 1179 (s), 890 (w), 825 cmÀ1 (m).
Keywords: amines · fluorescence · host–guest systems · ion
pairs · sensors
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Synthesis of probes ABA and BBA
For the synthesis of compounds (Z)-2-(4-aminophenyl)-3-(4-butoxy-
phenyl)acrylonitrile (ABA) and (Z)-3-(4-butoxyphenyl)-2-[4-(butyla-
mino)phenyl]acrylonitrile (BBA), a mixture of compound 2 (1.0 g,
4.23 mmol) dissolved in DMF (10 mL) and NaOH (339 mg,
8.46 mmol) was stirred for 15 min at RT. Then 1-bromobutane
(928.8 mg, 8.47 mmol) was added, and the mixture was sequential-
ly stirred for 12 h at 908C. The mixture was poured into water
(500 mL) and extracted with ethyl acetate (100 mL) three times. Fi-
nally, after silica gel column chromatography (n-hexane/EtOAc 6:1),
the two crude products were recrystallized from ethanol and water
to give the yellow powder ABA (824.3 mg, 66.3%) and BBA
(292.7 mg, 19.9%).
Compound ABA: 1H NMR ([D6]DMSO, 400 MHz): d=7.83 (d, J=
8.8 Hz, 2H; ArH), 7.60 (s, 1H; CH), 7.39 (d, J=8.4 Hz, 2H; ArH), 7.04
(d, J=8.8 Hz, 2H; ArH), 6.64 (d, J=8.4 Hz, 2H; ArH), 5.54 (s, 2H;
NH2), 4.03 (t, J=6.4 Hz, 2H; CH2), 1.71 (t, J=6.8 Hz, 2H; CH2), 1.44
(q, 2H; CH2), 0.94 ppm (t, 3H; CH3); 13C NMR ([D6]DMSO, 400 MHz):
d=159.7, 149.7, 136.6, 130.3, 126.8, 126.4, 121.1, 118.7, 114.7,
113.9, 107.8, 67.3, 30.6, 18.7, 13.6 ppm; FTIR (KBr): n˜ =3455 (vs),
3360 (vs), 3031 (s), 2956 (m), 2920 (s), 2852 (m), 2213 (m), 1797 (w),
1639 (s), 1606 (vs), 1564 (m), 1515 (s), 1466 (s), 1388 (w), 1357 (w),
1298 (s), 1257 (s), 1174 (s),1123 (s), 1069 (m), 1034 (m), 1002 (m),
896 (w), 827 (m), 803 (w), 766 (w), 721 (w), 628 cmÀ1 (w).
1
Compound BBA: H NMR (CDCl3, 400 MHz): d=7.83 (d, J=8.4 Hz,
2H; ArH), 7.60 (s, 1H; CH), 7.45 (d, J=8.4 Hz, 2H; ArH), 7.03 (d, J=
8.4 Hz, 2H; ArH), 6.64 (d, J=8.0 Hz, 2H; ArH), 6.06 (s, 1H; NH), 4.02
(t, 2H; CH2), 3.03 (t, 2H; CH2), 1.69 (m, 2H; CH2), 1.52 (m, 2H; CH2),
1.40 (m, 4H; 2CH2), 0.92 ppm (t, 6H; 2CH3); 13C NMR (CDCl3,
400 MHz): d=160.5, 147.1, 138.5, 130.7, 127.0, 126.8, 125.0, 118.9,
115.1, 114.8, 108.6, 68.2, 53.5, 31.6, 29.1, 25.7, 22.6, 14.1, 13.9 ppm;
FTIR (KBr): n˜ =3377 (vs), 3027 (s), 2958 (vs), 2930 (vs), 2871 (vs),
2211 (s), 1609 (vs), 1524 (vs), 1475 (s), 1418 (w), 1335 (vs), 1269 (vs),
1254 (vs), 1179 (vs), 1146 (w), 1124 (w), 1067 (w), 1309 (m), 1008
(m), 970 (w), 938 (m), 891 (vs), 767(w), 740 (w), 635 cmÀ1 (w).
CCDC-931697 (2), -975117 (ABA), -937566 (BBA), -987145 (ABAT),
and -987082 (BBAT) contain the supplementary crystallographic
data for this paper. These data can be obtained free of charge
from The Cambridge Crystallographic Data Centre via
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Acknowledgements
This work was supported by the National Natural Science
Foundation of China (21101001, 50873001, and 61107014), the
Natural Science Foundation of Anhui Province (1208085MB21),
the 211 Project of Anhui University, the Team for Scientific In-
novation Foundation of Anhui Province (2006KJ007TD), and
a strategic faculty grant in material science from the Swedish
government (SFO-Mat-Liu # 2009-00971).
Chem. Eur. J. 2014, 20, 12215 – 12222
12221
ꢀ 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim