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2.4.3 Data of 6c-AQ
2.4.7 Data of 14-AQ
Red powder; mp ¼ 182–1838C; Yield, 95%; Rf ¼ 0.67;
1H NMR (TMS, d ppm): 8.32–8.30 (q, 1H, H-6AQ), 8.22–
8.20 (q, 1H, H-7AQ), 7.92–7.82 (m, 2H, H-5AQ, H-8AQ),
7.65–7.61 (q, 1H, H-3AQ), 7.53–7.51 (q, 1H, H-4AQ),
7.34–7.31 (d, 1H, H-2AQ), 3.76–3.72 (m, 1H, H-CHa),
2.79 (s, 1H, NH), 1.86–1.51 (d, 8H, H-CHb2–c), 0.98–0.95
(m, 2H, H-CHc2); FT-IR (KBr plate, n cm21): 3247.73 (m,
Orange powder; mp ¼ 89–908C; Yield, 90%; Rf ¼ 0.75;
1H NMR (TMS, d ppm): 8.32–8.30 (q, 1H, H-6AQ), 8.22–
8.20 (q, 1H, H-7AQ), 7.92–7.82 (m, 2H, H-5AQ, H-8AQ),
7.68–7.64 (q, 1H, H-3AQ), 7.55–7.53 (q, 1H, H-4AQ),
7.30–7.27 (d, 1H, H-2AQ), 3.47–3.44 (q, 2H, H-CHa2),
2.80 (s, 1H, NH), 1.83–1.80 (m, 2H, H-CHb2), 1.58–1.51
(m, 2H, H-CHc2), 1.46–1.29 (m, 20H, H-CHd2–m), 0.90–
0.87 (t, 3H, H-CHn3); FT-IR (KBr plate, n cm21): 3298.17
(m, nNZH), 1628.94 (m, dNZH), 1661.54 (vs, br, nCvO).
n
NZH), 1630.06 (m, dNZH), 1662.28 (vs, br, nCvO).
2.4.4 Data of 6-AQ
2.4.8 Data of 16-AQ
1
Red powder; mp ¼ 80–818C; Yield, 91%; Rf ¼ 0.65; H
NMR (TMS, d ppm): 8.28–8.26 (q, 1H, H-6AQ), 8.20–
8.18 (q, 1H, H-7AQ), 7.90–7.80 (m, 2H, H-5AQ, H-8AQ),
7.64–7.60 (q, 1H, H-3AQ), 7.51–7.49 (q, 1H, H-4AQ),
7.24–7.13 (d, 1H, H-2AQ), 2.80 (s, 1H, NH), 1.82–1.75
(m, 2H, H-CHb2), 1.55–1.50 (m, 2H, H-CHc2), 1.43–1.36
(m, 4H, H-CH2d–e), 0.95–0.92 (t, 3H, H-CHf3); 13C NMR
(400 MHz, CD3COCD3, r.t., TMS, d ppm): 184.46 (CvO),
182.91 (CvO), 151.85, 135.32, 134.94, 134.52, 134.02,
133.06, 132.96, 126.48, 126.23, 118.07, 114.87, 112.53 (C
of benzene rings), 42.56 (NHZC H2), 31.39–13.40
(11C b–f); FT-IR (KBr plate, n cm21): 3242.77 (m,
Orange powder; mp ¼ 89–908C; Yield, 82%; Rf ¼ 0.75;
1H NMR (TMS, d ppm): 8.32–8.30 (d, 1H, H-6AQ), 8.22–
8.20 (d, 1H, H-7AQ), 7.90–7.80 (m, 2H, H-5AQ, H-8AQ),
7.66–7.62 (t, 1H, H-3AQ), 7.55–7.53 (d, 1H, H-4AQ),
7.28–7.25 (d, 1H, H-2AQ), 3.48–3.43 (q, 2H, H-CHa2),
2.61 (s, 1H, NH), 1.85–1.78 (m, 2H, H-CHb2), 1.60–1.53
(m, 2H, H-CHc2), 1.47–1.31 (m, 24H, H-CHd2–o), 0.90–
0.88 (t, 3H, H-CHp3); FT-IR (KBr plate, n cm21): 3241.88
(m, nNZH), 1628.44 (m, dNZH), 1669.11 (vs, br, nCvO).
2.4.9 Data of 18-AQ
n
NZH), 1627.57 (m, dNZH), 1665.81 (vs, br, nCvO).
Orange powder; mp ¼ 85–868C; Yield, 87%; Rf ¼ 0.76;
1H NMR (TMS, d ppm): 8.23 (d, 1H, H-6AQ), 8.21–8.20
(d, 1H, H-7AQ), 7.94–7.82 (m, 2H, H-5AQ, H-8AQ), 7.70–
7.67 (t, 1H, H-3AQ), 7.56–7.53 (q, 1H, H-4AQ), 7.31–7.28
(q, 1H, H-2AQ), 3.50–3.43 (q, 2H, H-CH2a), 2.85 (s, 1H,
NH), 1.87–1.76 (m, 2H, H-CHb2), 1.56–1.51 (m, 2H,
H-CHc2), 1.45–1.29 (m, 28H, H-CHd2–q), 0.91–0.86 (t, 3H,
H-CHr3); FT-IR (KBr plate, n cm21): 3242.34 (m, nNZH),
1628.74 (m, dNZH), 1669.36 (vs, br, nCvO).
2.4.5 Data of 10-AQ
1
Red powder; mp ¼ 82–838C; Yield, 87%; Rf ¼ 0.63; H
NMR (TMS, d ppm): 8.33–8.30 (q, 1H, H-6AQ), 8.23–
8.20 (q, 1H, H-7AQ), 7.94–7.82 (m, 2H, H-5AQ, H-8AQ),
7.70–7.64 (t, 1H, H-3AQ), 7.55–7.52 (q, 1H, H-4AQ),
7.30–7.28 (d, 1H, H-2AQ), 3.50–3.43 (q, 2H, H-CHa2),
2.84 (s, 1H, NH), 1.86–1.76 (m, 2H, H-CHb2), 1.60–1.50
(m, 2H, H-CHc2), 1.46–1.30 (m, 12H, H-CHd2–i), 0.91–
0.86 (t, 3H, H-CHj3); FT-IR (KBr plate, n cm21): 3296.63
(m, nNZH), 1628.73 (m, dNZH), 1661.70 (vs, br, nCvO).
2.5 Preparation of vesicles
Two equimolar solutions, one of n-AQ and the other of CD,
were prepared with triply distilled water and methanol (1:1,
by volume). All sample solutions for the investigation were
freshly prepared by diluting the stock solution. Considering
the poor solubility of n-AQ, the proper concentration for
the vesicular formation was tested and chosen to be
1025 mol/l, for both n-AQ and CD. The sample solutions
contained the same volume of n-AQ (2 £ 1025 mol/l) and
of CD (2 £ 1025 mol/l) solutions, and then ultrasonicated
for 20 min at 300 K before detection.
2.4.6 Data of 12-AQ
Orange powder; mp ¼ 83.8–84.18C; Yield, 84%;
1
Rf ¼ 0.75; H NMR (TMS, d ppm): 8.29–8.27 (q, 1H,
H-6AQ), 8.21–8.18 (q, 1H, H-7AQ), 7.90–7.81 (m, 2H, H-
5AQ, H-8AQ), 7.65–7.61 (q, 1H, H-3AQ), 7.52–7.50 (q, 1H,
H-4AQ), 7.25–7.23 (d, 1H, H-2AQ), 3.45–3.40 (q, 2H,
H-CHa2), 2.80 (s, 1H, NH), 1.83–1.76 (m, 2H, H-CHb2),
1.56–1.50 (m, 2H, H-CHc2), 1.45–1.29 (m, 16H,
H-CHd2–k), 0.90 (t, 3H, H-CHl3 ); 13C NMR (400 MHz,
CD3COCD3, r.t., TMS, d ppm): 184.47 (CvO), 182.91
(CvO), 151.87, 135.33, 134.94, 134.53, 134.03, 133.07,
132.96, 126.48, 126.24, 118.09, 114.88, 112.54 (C of
benzene rings), 42.54 (NH-C H2), 31.74–13.44 (11C b–l);
FT-IR (KBr plate, n cm21): 3296.44 (m, nNZH), 1629.03
(m, dNZH), 1661.94 (vs, br, nCvO).
The effect of an external stimulus was investigated by
adding an external irritant to the sample solutions.
2.6 Detection of the stoichiometries of the n-AQ/b-CD
complex
Two equimolar stock solutions (1024 mol/l), one of n-AQ
(g) and the other of b-CD (h), were prepared. A set of