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Ar H), 7.32 7.36 (m, 3H, Ar H), 7.18 7.22 (m, 4H, Ar H), 4.24 4.38
(q, 4H, N CH2), 2.78 (s, 6H, CH3), 1.58 (s, 6H, CH3), 1.42 1.52 (t, 6H,
CH3). 13C NMR (100 MHz, CDCl3):
d 155.4, 147.6, 146.5, 141.8, 141.2,
138.4,137.0,136.2, 134.5, 132.6, 131.5, 131.0, 129.7,128.1, 126.8, 125.7,
125.1, 123.6, 122.4, 121.7, 116.2, 96.2, 81.8, 37.8, 16.2, 14.7, 13.8. TOF
MS EIþ calcd for C51H41BF2N4 758.3392, found 758.3387.
4.1.4. 2,6 Di (4 N,N diphenyl phenylacetylenyl) 1,3,5,7 tetramethyl
8 phenyl 4,4 difluoroboradiazaindacene (3c). Prepared according to
the general procedure with N (4 ethynylphenyl) N phenyl
benzenamine (134 mg, 0.497 mmol), 2 (100 mg, 0.207 mmol) in
DMF (4 mL). Complete consumption of the starting material was
observed after 12 h. The chromatography was performed on silica
(CH2Cl2/hexane, 3:2). The green colored fraction was collected to
get the compound. Yield: 121 mg (68%); mp 258 259 ꢀC. 1H NMR
(400 MHz, CDCl3): 7.42 7.52 (m, 6H, Ar H), 7.35 7.38 (m, 6H, Ar
H), 7.22 7.30 (m, 6H, Ar H), 7.00 7.18 (m, 15H, Ar H), 2.68 (s, 6H,
´
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CH3), 1.26 (s, 6H, CH3). 13C NMR (100 MHz, CDCl3):
d 156.7, 148.0,
147.3, 142.1, 141.4, 138.2, 137.8, 134.1, 133.8, 132.4, 129.6, 128.6, 127.4,
125.0, 123.5, 122.7, 116.5, 96.5, 80.9, 14.8, 13.9. TOF MS EIþ calcd for
C59H45BF2N4 858.3705, found 858.3709.
Acknowledgements
This work was supported by National Natural Science Founda
tion of China (No. 20572012, 20876022, 20536010, 10674031) and
Program for Changjiang Scholars and Innovative Research Team in
University (IRT0711).
`
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Supplementary data
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Xiao, Y.; Yu, G.; Liu, Y.; Qian, X. Chem. Commun. 2008, 4777–4779.
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Supplementary data associated with this article can be found in
´
Beljonne, D.; Bredas, J.-L. J. Am. Chem. Soc. 2000, 122, 9500–9510; (b) Lee, W.-H.;
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Please cite this article in press as: Zhang, D. et al., Tetrahedron (2009), doi:10.1016/j.tet.2009.08.002