CDCl
quat). MS (70 eV), m/z (%): 330 (100) [M ], 315 (48) [M
CH ], 297 (22), 282 (17), 269 (15), 221 (13), 165 (15), 132 (13), 84
16). HRMS (EI) calcd for C18 : 330.0571; found: 330.0569.
Note: This compound slowly decomposes on contact with air at
room temperature. It should be stored at low temperature in inert
gas atmosphere.
3
, plus DEPT, ppm): d = 18.2 (+, CH
3
), 128.4 (Cquat), 132.2
17 M. E. Weiss, Dissertation, Universit a¨ t GH Essen, 2000.
+
+
18 (a) Reviews: H. Hopf and G. Maas, Angew. Chem., 1992, 104, 953;
H. Hopf and G. Maas, Angew. Chem., Int. Ed. Engl., 1992, 31, 931;
(
C
-
3
(
b) H. Hopf, G. Maas, in The Chemistry of Dienes and Polyenes (Ed.:
(
H
18
S
3
Z. Rappoport,), Vol. 1, J. Wiley, & Sons: Chichester, 1997, pp. 927.
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1
997, C53, 920; (c) C. Domene, P. W. Fowler, L. W. Jenneskens and E.
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2
0 (a) Reviews, see: G. Zotti, B. Vercelli and A. Berlin, Acc. Chem. Res.,
2
008, 41, 1098; (b) Y. Le, Y. Umemoto, M. Nitani and Y. Aso, Pure Appl.
Acknowledgements
Chem., 2008, 80, 589; (c) G. Horowitz, P. Delannoy, in Handbook of
Oligo- and Polythiophenes (Ed.: D. Fichou,), Wiley-VCH: Weinheim,
Part of this work was supported by the National Science Council
of Taiwan (NSC 94-2113-M-006-019). K.K.B. is grateful to the
Schweizerischer Nationalfonds for support of this work. We also
thank Prof. S.-L. Wang and Ms. C.-Y. Chen (National Tsing-Hua
University, Taiwan) for the X-ray structure analyses, and Prof. Jay
S. Siegel (University of Zurich) for valuable discussions over the
course of this work.
1
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2
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3
4
Some 4,5-disubstituted phenanthrenes (A-F, A-Cl, A-CH
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5
6
7
24 Tribromobenzo[1,2-c:3,4-c¢:5,6-c¢¢]trithiophenes can be prepared in the
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26 Compound C-Me: C18
18 3
H S , monoclinic crystals of space group
C2/c, unit cell dimensions: a = 20.700(3), b = 8.1002(11), c =
◦
3
19.248(3) A
˚
, a = 90, b = 94.392(2), g = 90 , V = 3217.9(7) A˚ .
CCDC 715338 and 715339†.
8
9
(a) Perchlorotriphenylene (B-Cl): K. Shibata, A. A. Kulkarni, D. M.
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28 Mainly, the methyl groups C13 and C14 break the perfect C symmetry.
2
29 It was observed that a highly congestive thiophene, such as 3,4-di-
1
995, 60, 428.
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0 Perbicyclo[2.2.2]octenetriphenylene (B-bco): This compound has been
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31 The end-to-end twist of ring I was determined by the torsion angle (C’s
2
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1
1 (a) C -Hexabenzotriphenylene (B-hbz-C
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1
1
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5 H. Hart and M. Sasaoka, J. Am. Chem. Soc., 1978, 100, 4326.
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2
754 | Org. Biomol. Chem., 2009, 7, 2748–2755
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