9
1
Mp = 154.5-157.5 °C; H-NMR (400 MHz, CDCl ): δ (ppm)
CCHC), 6.82-6.90 (m, 8H, CCHCH), 7.00-7.06 (m, 8H,
13
ACCEPTED MANUSCRIPT
3
=
0.12-1.64 (m, 23H, CH CH CH ), 1.87-1.95 (m, 1H,
CCHCH); C-NMR (100 MHz, CDCl ): δ (ppm) = 25.8 (CH ),
3 2
2
2
2
CH CH CO, hh), 1.98-2.09 (m, 4H, CH CHCH ), 2.15-2.25 (m,
26.0 (CH ), 30.5 (CH ), 32.8 (CH ), 63.0 (CH ), 64.0 (CH), 65.0
2
2
2
2
2 2 2 2
3
H, CH CO, ht), 2.74 (t, J=7 Hz, 1H, CH CO, hh), 3.78 (s, 1.5H,
(CH ), 89.3 (C), 125.1 (CH), 125.6 (CH), 125.8 (CH), 127.6
2
−1
2
2
CCHC, ht), 4.48 (s, 0.5H, CCHC, hh), 4.90-5.04 (m, 4H,
(CH), 141.0 (C), 142.1 (C); IR vmax cm : 3341, 2934, 2858,
CH CHCH ), 5.12-5.27 (m, 4H, CCH O), 5.74-5.87 (m, 2H,
1452, 1292, 1254, 1202, 1154, 1118, 1052; HRMS (m/z for
2
2
2
13
+
CH CHCH ), 6.81-7.15 (m, 16H, CCHCHCHCHC); C-NMR
[MNH ] ) calcd.: 606.3583; found: 606.3574
2
2
4
(
(
(
(
(
100 MHz, CDCl ): δ (ppm) = 24.9 (CH ), 28.9 (CH ), 29.0
3
2
2
4
.20. (18)2
CH ), 29.0 (CH ), 29.1 (CH ), 29.2 (CH ), 29.4 (CH ), 33.8
2
2
2
2
2
1
CH ), 34.3 (CH ), 59.0 (CH), 63.4 (CH ), 68.9 (CH ), 114.2
2
2
2
2
Mp = 118-118.5 °C; H-NMR (500 MHz, CDCl ): δ (ppm) =
3
CH ), 124.7 (CH), 125.8 (CH), 127.7 (CH), 128.0 (CH), 139.2
2
1.24-1.47 (m, 36H), 1.54-1.62 (m, 4H, COCH CH ), 1.85 (quin,
2 2
J=7.2 Hz, 4H, CH CH OH) 3.53 (t, J=7.1 Hz, 4H, COCH ), 3.65
−1
CH), 142.1 (C), 143.9 (C), 174.5 (C); IR vmax cm : 2926, 2852,
2
2
2
1
724, 1640, 1454, 1382, 1344, 1292, 1242, 1176, 1116, 1070
(t, J=6.7 Hz, 4H, CH OH), 4.46 (s, 2H, CCHC), 6.82-6.89 (m,
2
1
3
8
H, CCHCH), 7.00-7.07 (m, 8H, CCHCH); C-NMR (125 MHz,
4
.16. (9)2
CDCl ): δ (ppm) = 25.3 (CH ), 25.8 (CH ), 26.2 (CH ), 29.5
(CH ), 29.6 (CH ), 32.8 (CH ), 63.1 (CH ), 65.1 (CH ), 89.2 (C),
3
2
2
2
1
Mp = 182-183 °C; H-NMR (500 MHz, CDCl ): δ (ppm) =
3
2 2 2 2 2
2
.13 (q, J=7.3 Hz, 4H, CCH CH CH), 2.76-2.82 (m, 4H,
125.1 (CH), 125.8 (CH), 127.5 (CH), 141.0 (C), 142.2 (C) );
−1
2
2
CCH CH CH), 3.88 (s, 2H, CCHC), 5.10 (d, J=10.2 Hz, 2H,
CH CHCH ), 5.15 (d, J=17.1 Hz, 2H, CH CHCH ), 6.04 (ddt,
IR vmax cm : 3324, 2920, 2850, 1452, 1290, 1256, 1202, 1154,
2
2
+
1118, 1056; HRMS (m/z for [MH] ) calcd.: 757.5196; found:
2
2
2
2
J=16.9 Hz, J=10.3 Hz, J=6.5 Hz, 2H, CH CHCH ), 6.79-6.93 (m,
757.5181
2
2
13
1
2H, CCHCHCHCHC), 6.99 (d, J=7.5 Hz, 4H, CCHCH); C-
4
.21. (19)2
NMR (125 MHz, CDCl ): δ (ppm) = 29.3 (CH ), 36.2 (CH ),
3
2
2
1
5
1
6.5 (C), 64.8 (CH), 114.5 (CH ), 125.2 (CH), 125.3 (CH),
2
Mp = 150-151 °C; H-NMR (400 MHz, CDCl ): δ (ppm) =
3
26.2 (CH), 127.5 (CH), 138.6 (CH), 142.7 (C), 143.7 (C);
1
.27-1.62 (20H), 1.78-2.00 (m, 4H, COCH CH ), 2.07 (q, J=6.9
Hz, 4H, CH CHCH ), 2.70-2.80 (m, 4H, COCH CH ), 4.57-4.74
1.35H, CCHC), 4.95 (dt, J=10.2 Hz, J=1 Hz, 2H, CH CHCH ),
2
2
−1
IR vmax cm : 3066, 3018, 2930, 2862, 2160, 2032, 1976, 1640,
1
2
2
2
2
+
472, 1448, 1122, 1046; GC-MS (m/z) 232 [M/2]
(
2 2
5
.02 (dq, J=17.1 Hz, J=1.7 Hz, 2H, CH CHCH ), 5.09-5.22
2 2
4
.17. (10)2
(0.65H, CCHC), 5.84 (ddt, J=17 Hz, J=10.3 Hz, J=6.6 Hz, 2H,
1
13
Mp = 111.5-114 °C; H-NMR (500 MHz, CDCl ): δ (ppm) =
CH CHCH ), 6.66-7.33 (16H, CCHCHCHCHC); C-NMR (100
3
2 2
1
2
.23-1.43 (m, 28H, CH CH CH ), 1.47-1.59 (m, 4H, CCH CH ),
MHz, CDCl ): δ (ppm) = 25.2 (CH ), 29.0 (CH ), 29.1 (CH ),
3 2 2 2
2
2
2
2
2
.05 (q, J=7.1 Hz, 4H, CH CHCH ), 2.65 (t, J=7.9 Hz, 4H,
29.4 (CH ), 29.4 (CH ), 33.8 (CH ), 114.2 (CH ), 125.6 (CH),
2 2 2 2
−1
2
2
CCH CH ), 3.84 (s, 2H, CCHC), 4.94 (d, J=10.2 Hz, 2H,
126.2 (CH), 139.2 (CH); IR vmax cm : 3066, 3032, 2924, 2850,
2
2
CH CHCH ), 5.00 (d, J=17.1 Hz, 2H, CH CHCH ), 5.83 (ddt,
2160, 2020, 1978, 1744, 1640, 1452, 1376, 1294, 1210, 1154,
2
2
2
2
+
J=17.1 Hz, J=10.3 Hz, J=6.7 Hz, 2H, CH CHCH ), 6.77-6.89 (m,
1118, 1010; HRMS (m/z for [MNH ] ) calcd.: 738.4522; found:
2
2
4
13
1
2H, CCHCHCHCHC), 6.96 (d, J=7.5 Hz, 4H, CCHCH); C-
738.4537
NMR (125 MHz, CDCl ): δ (ppm) = 24.9 (CH ), 29.0 (CH ),
3
2
2
2
9.2 (CH ), 29.5 (CH ), 29.5 (CH ), 29.6 (CH ), 29.6 (CH ), 30.7
Acknowledgements
2
2
2
2
2
(
CH ), 33.8 (CH ), 37.8 (CH ), 56.6 (C), 65.0 (CH), 114.1 (CH ),
2
2
2
2
1
1
1
25.1 (CH), 126.2 (CH), 127.4 (CH), 139.3 (CH), 143.0 (C),
43.9 (C); IR vmax cm : 2924, 2852, 2530, 2478, 2160, 2028,
978, 1734, 1450, 1364, 1328, 1252, 1166, 1096
JVD would like to thank Flanders Innovation
&
−1
Entrepreneurship for a PhD-scholarship. FDP and OvdB thank
the Research Foundation-Flanders (FWO) for financial support.
We would also like to thank Akın Gürsoy and Türkan Gençoğlu
for their help during synthesis. Kevin De Bruycker is
acknowledged for computational calculations.
4
.18. (14)2
1
Mp = 83.5-85 °C; H-NMR (500 MHz, CDCl ): δ (ppm) =
3
1
.18-1.39 (m, 20H, CH CH CH ), 1.67 (quin, J=6.7 Hz, 4H,
2
2
2
OCH CH ), 2.02 (q, J=7.1 Hz, 4H, CH CHCH ), 4.31 (t, 4H,
References
2
2
2
2
OCH CH ) , 4.93 (dt, J=10.1 Hz, J=1.1 Hz, 2H, CH CHCH ),
2
2
2
2
4
.93 (dq, J=17.1 Hz, J=1.8 Hz, 2H, CH CHCH ), 5.74 (s, 2H,
1.
2.
3.
Fritzsche, J. Prakt. Chem. 1867, 101 (1), 333-343.
Becker, H. D., Chem. Rev. 1993, 93, 145-172.
Breton, G. W.; Vang, X., J. Chem. Educ. 1998, 75, 81.
(a) Bratschkov, C.; Karpuzova, P.; Müllen, K.; Klapper,
2
2
CCHC), 5.74 (ddt, J=17.1 Hz, J=10.3 Hz, J=6.7 Hz, 2H,
CH CHCH ), 6.65 (dd, J=7.5 Hz, J=1.4 Hz, 2H, CCHCH), 6.79-
6
CCHCH); C-NMR (125 MHz, CDCl ): δ (ppm) = 26.1 (CH ),
2
2
2
.86 (m, 4H, CCHCH), 7.00 (dd, J=7.1 Hz, J=1.6 Hz, 2H,
4
.
13
3
2
M.; Schopov, I., Polym. Bull. 2001, 46 (5), 345-349; (b) Bruss, J. M.;
Sahyun, M. R. V.; Schmidt, E.; Sharma, D. K., J. Polym. Sci., Part
A: Polym. Chem. 1993, 31 (4), 987-994; (c) Matsui, J.; Ochi, Y.;
Tamaki, K., Chem. Lett. 2006, 35 (1), 80-81.
8.4 (CH ), 28.9 (CH ), 29.1 (CH ), 29.1 (CH ), 29.3 (CH ), 29.4
2 2 2 2 2
(CH ), 33.8 (CH ), 55.0 (CH), 66.2 (C), 114.1 (CH ), 125.5 (CH),
2
2
2
1
1
2
7
26.1 (CH), 126.5 (CH), 128.2 (CH), 139.2 (CH), 141.9 (C),
−1
42.7 (C), 174.5 (C); IR vmax cm : 3072, 3024, 2922, 2852, 2160,
5
.
Islangulov, R. R.; Kozlov, D. V.; Castellano, F. N., Chem.
030, 1978, 1722, 1640, 1454, 1198, 1104, 1006; LC-MS (m/z)
+
+
Commun. 2005, (30), 3776-3778.
66.4 [MNH ] ; HRMS (m/z for [MNH ] ) calcd.: 766.4835;
4
4
found: 766.4830
6.
Morris, J. V.; Mahaney, M. A.; Huber, J. R., J. Phys.
Chem. 1976, 80, 969-974.
4
.19. (17)2
7
.
(a) Bouas-Laurent, H.; Castellan, A.; Desvergne, J.-P.;
1
Mp = 117-119 °C; H-NMR (400 MHz, CDCl ): δ (ppm) =
.42-1.55 (m, 10H, CH CH CH ), 1.65 (quin, J=6.8 Hz, 4H,
Lapouyade, R., Chemical Society Reviews 2000, 29 (1), 43-55; (b)
Ihmels, H.; Luo, J., Journal of Photochemistry and Photobiology A:
Chemistry 2008, 200 (1), 3-9; (c) Bouas-Laurent, H.; Castellan, A.;
3
1
2
2
2
COCH CH ), 1.87 (quin, J=7 Hz, 4H, CH CH OH), 3.53 (t, J=7
Hz, 4H, COCH ), 3.69 (t, J=6.5 Hz, 4H, CH OH), 4.46 (s, 2H,
2
2
2
2
2
2