R. Gresser et al.
J=7.9, 2H), 7.93 (d, J=8.1 Hz, 4H), 7.40 (t, J=7.7 Hz, 2H), 7.38 (t, J=
7.0 Hz, 4H), 7.30 (d, J=7.0 Hz, 2H), 2.47 ppm (s, 6H); 13C NMR
(126 MHz, CDCl3): d=148.3, 143.6, 139.7, 135.3, 130.4, 129.9, 129.8,
127.6, 127.3, 126.4, 122.1, 121.2, 21.5 ppm; ES-MS: m/z: 426 [M+H]+; el-
emental analysis calcd (%) for C30H23N3: C 84.68, H 5.45, N 9.87; found:
C 84.79, H 5.47, N 9.65.
calcd (%) for C30H22N3F2B: C 76.13, H 4.68, N 8.88; found: C 76.37, H
5.22, N 8.89.
Compound 10e: Yield: 65%;: m.p. 2548C (from dichloromethane/hexane
2:1); 1H NMR (500 MHz, CDCl3): d=8.10 (d, J=8.0 Hz, 2H), 7.90 (d,
J=8.8, 4H), 7.65 (d, J=8.0 Hz, 2H), 7.48 (t, J=7.1 Hz, 4H), 7.29 (t, J=
7.1 Hz, 2H), 7.04 (d, J=8.8 Hz, 2H), 3.88 ppm (s, 6H); 13C NMR
(126 MHz, CDCl3): d=161.3, 152.4, 139.1, 133.5, 132.0, 131.0, 130.1,
126.8, 124.1, 122.9, 121.1, 114.1, 55.3 ppm; 19F NMR (282 MHz, CDCl3):
d=129.7 ppm (q, J=31.0); ES-MS: m/z: 506 [M+H]+; elemental analysis
calcd (%) for C30H22N3O2BF2: C 71.16, H 4.57, N 8.29; found: C 71.14, H
4.58, N 8.22.
Compound 9e: Yield: 30%; m.p. 2468C (from dichloromethane/hexane
2:1); 1H NMR (500 MHz, CDCl3): d=8.10 (d, J=7.9 Hz, 2H), 7.97 (d,
J=8.8, 4H), 7.91 (d, J=8.0 Hz, 2H), 7.37 (t, J=7.0 Hz, 4H), 7.29 (t, J=
7.0 Hz, 2H), 7.08 (d, J=8.8 Hz, 2H), 3.91 ppm (s, 6H); 13C NMR
(126 MHz, CDCl3): d=160.6, 147.6, 143.4, 135.3, 129.6, 129.2, 127.2,
126.1, 125.9, 122.1, 121.2, 114.7, 55.5 ppm; ES-MS: m/z: 458 [M+H]+; el-
emental analysis calcd (%) for C30H23N3O2: C 78.75, H 5.07, N 9.18;
found: C 78.43, H 4.99, N 9.02.
Compound 10 f: Yield: 54%; m.p. 2608C (from trichloromethane);
1H NMR (500 MHz, CDCl3): d=8.06–8.10 (m, 6H), 7.47 (d, J=6.5 Hz,
2H), 7.36 (t, J=6.5 Hz, 2H), 6.97 (d, J=3.5 Hz, 2H), 2.62 ppm (s, 6H);
13C NMR (126 MHz, CDCl3): d=147.2, 143.7, 140.2, 134.0, 133.2, 131.0,
130.0, 129.7, 127.7, 127.3, 124.4, 121.3, 15.7 ppm; 19F NMR (282 MHz,
CDCl3): d=133.9 ppm (q, J=31.0); ES-MS: m/z: 486 [M+H]+; elemental
analysis calcd (%) for C26H18N3S2BF2: C 64.34, H 3.74, N 8.66, S 13.21;
found: C 63.72, H 3.45, N 8.20, S 13.38.
Compound 9 f: Yield: 21%; m.p. 2428C (from trichloromethane);
1H NMR (500 MHz, CDCl3): d=8.06 (d, J=7.9 Hz, 2H), 7.93 (d, J=
7.9 Hz 2H), 7.63 (s, 2H), 7.39 (d, J=7.3 Hz, 2H), 7.31 (t, J=7.3 Hz, 2H),
6.90 (d, J=3.7 Hz, 2H), 2.61 ppm (s, 6H); 13C NMR (126 MHz, CDCl3):
d=143.9, 143.6, 141.7, 135.0, 134.5, 129.4, 127.4, 127.3, 127.2, 126.2, 121.7,
121.2, 15.8 ppm; ES-MS: m/z: 438 [M+H]+; elemental analysis calcd (%)
for C26H19N3S2: C 71.36, H 4.38, N 9.60, S 14.66 found: C 71.57, H 4.18,
N 9.65, S 14.58.
Acknowledgements
General procedure for the preparation of 10a–f: Compound
9
(12.6 mmol) was dissolved in dichloroethane (150 mL) and diisopropyle-
thylamine (10.5 mL, 60.8 mmol) was added. The mixture was stirred for
1 h and BF3·OEt2 (7.5 mL, 60.5 mmol) was added at room temperature.
Then the mixture was heated at reflux until complete conversion of the
starting material was observed (monitored by thin layer chromatography
(TLC), ca. 2 h). The cold reaction mixture was quenched with water and
extracted twice with dichloromethane (100 mL). The combined organic
phases were dried and concentrated in vacuo. The crude product was pu-
rified by flash chromatography (dichloromethane/hexane). By this proce-
dure the following compounds have been prepared:
The authors gratefully acknowledge the financial support by the Federal
Ministry for Education and Research (BMBF) within the Innoprofile
program (03IP602) and the computational resources from the Center for
Information Services and High Performance Computing (ZIH), TU
Dresden.
[3] a) A. Hepp, G. Ulrich, R. Schmechel, H. von Seggern, R. Ziessel,
Kleeberg, S. Kçhler, X. Xie, B. Ventura, L. Flamigni, Chem. Eur. J.
pomnyashchii, M. Brçring, J. Ahrens, R. Krꢀger, A. J. Bard, J. Phys.
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vino, T. Bura, J. Mater. Chem. 2009, 19, 2298–2300.
b) M. Tsutayoshi, S. Kenichi, N. Taizo, T. Takashi, T. Hirosuke, JP
11092479, 1997.
Compound 10a: Yield: 62%, m.p. 2718C (from trichloromethane/hexane
4:1); 1H NMR (500 MHz, CDCl3): d=8.10 (d, J=8.0 Hz, 2H), 7.50 (t,
J=7.9 Hz 2H), 7.44 (d, J=7.9 Hz,1H), 7.38 (d, J=7.5 Hz, 1H), 7.34 (t,
J=7.5 Hz, 2H), 7.21–7.28 (m, 8H), 2.18 (s, 3H), 2.15 ppm (s, 3H);
13C NMR (126 MHz, CDCl3): d=154.2, 138.6, 137.2, 133.1, 131.5, 130.6,
130.0, 129.9, 129.8, 129.7, 126.7, 125.2, 123.7, 121.0, 20.0 ppm; 19F NMR
(282 MHz, CDCl3): d=127.2 (o, J=31.0), 136.4 (q, J=31.0), 145.6 ppm
(q, J=31.0); ES-MS: m/z: 474 [M+H]+; elemental analysis calcd (%) for
C30H22N3BF3: C 76.13, H 4.68, N 8.88; found: C 75.72, H 4.55, N 8.70.
Compound 10b: Yield: 56%; m.p. 3028C (from hexane/ethyl acetate
5:1); 1H NMR (500 MHz, CDCl3): d=8.07 (d, J=8.0 Hz, 1H), 8.06 (d,
J=8.0 Hz, 1H), 7.67 (d, J=7.5 Hz 1H), 7.55(d, J=7.5 Hz, 1H), 7.41–7.47
(m, 4H), 7.31 (d, J=7.5 Hz, 1H), 7.21–7.28 (m, 2H), 7.06 (t, J=7.5 Hz,
1H), 7.00 (t, J=8.3 Hz, 1H), 6.98 (t, J=8.3 Hz, 2H), 3.77 (s, 3H),
3.69 ppm (s, 3H); 13C NMR (126 MHz, CDCl3): d=157.7, 151.4, 151.1,
139.0, 131.7, 130.0, 126.2, 124.2, 120.8, 120.4, 119.6, 111.2, 111.0,
55.6 ppm; 19F NMR (282 MHz, CDCl3): d=118.0 (o, J=31.0), 133.1 (q,
J=31.0), 149.0 ppm (q, J=31.0); ES-MS: m/z: 506 [M+H]+; elemental
analysis calcd (%) for C30H22N3O2BF2: C 71.16, H 4.57, N 8.29; found: C
70.34, H 4.27, N 7.48.
[7] M. Riede, T. Mueller, W. Tress, R. Schueppel, K. Leo, Nanotechnol-
Compound 10c: Yield: 78%; m.p. 2728C (from dichloromethane/hexane
2:1); 1H NMR (500 MHz, CDCl3): d=8.11 (d, J= Hz, 2H), 7.87 (dd, J=
2.3; 7.9 Hz, 4H), 7.62 (d, J=8.1 Hz, 1H), 7.49–7.53ACTHNUGRTENUNG(m, 8H), 7.31 ppm (t,
[8] a) L. H. Thoresen, H. Kim, M. B. Welch, A. Burghart, K. Burgess,
L. H. Thoresen, J. Reibenspies, K. Burgess, F. Bergstrçm, L. B.-A.
[9] T. H. Allik, R. E. Hermes, G. Sathyamoorthi, J. H. Boyer, Proc.
SPIE-Int. Soc. Opt. Eng. 1994, 2115, 240–248.
J=7.6 Hz, 2H); 13C NMR (126 MHz, CDCl3): d=153.2, 139.3, 133.6,
131.1, 130.5, 130.3, 130.2, 130.3, 128.5, 127.0, 124.1, 121.2 ppm; 19F NMR
(282 MHz, CDCl3): d=129.5 ppm (q, J=31.0); ES-MS: m/z: 446
[M+H]+; elemental analysis calcd (%) for C28H18N3F2B: C 75.53, H 4.07,
N 9.44; found: C 75.33, H 3.94, N 9.27.
Compound 10d: Yield: 74%; m.p. 3198C (from dichloromethane/hexane
2:1); 1H NMR (500 MHz, CDCl3): d=8.10 (d, J=8.1 Hz, 2H), 7.79 (d,
J=8.1, 4H), 7.63 (d, J=8.1 Hz, 2H), 7.49 (t, J=7.1 Hz, 2H), 7.31 (t, J=
8.1 Hz, 4H), 7.29 (d, J=7.1 Hz, 2H), 2.43 ppm (s, 6H); 13C NMR
(126 MHz, CDCl3): d=153.2, 140.7, 139.2, 133.5, 131.1, 130.2, 130.1,
129.2, 127.5, 126.8, 124.2, 121.1, 21.6 ppm; 19F NMR (282 MHz, CDCl3):
d=129.5 ppm (q, J=31.0); ES-MS: m/z: 474 [M+H]+; elemental analysis
[10] a) Y. Wu, D. H. Klaubert, H. C. Kang, Y.-Z. Zhang, US Patent
6005113, 1999; b) J. H. Boyer, L. R. Morgan, US Patent 5189029,
1993; c) G. Ulrich, S. Goeb, A. De Nicola, P. Retailleau, R. Ziessel,
Okujima, Y. Tomimori, J. Nakamura, H. Yamada, H. Uno, N. Ono,
2946
ꢂ 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Chem. Eur. J. 2011, 17, 2939 – 2947