7906
M. Lu et al. / Tetrahedron Letters 43 (2002) 7903–7906
13. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron
6. Grayson, S. M.; Fre´chet, J. M. J. Chem. Rev. 2001, 101,
3819.
Lett. 1975, 4467.
14. Golt, A.; Ziener, U. J. Org. Chem. 1997, 62, 6137.
15. G1: Mp: 96–98°C. 1H NMR (CDCl3, 400 MHz) l 0.88 (t,
J=6.0 Hz, 6H, CH2CH3), 1.2–1.4 (m, 36H, (CH2)9), 1.74
(m, 4H, CH2), 3.11 (t, J=7.6 Hz, 4H, SCH2), 3.97 (s, 6H,
OCH3), 7.07 (s, 4H, Ar-H), 7.70 (d, J=6.8 Hz, 4H,
Ar-H), 7.90 (d, J=6.8 Hz, 4H, Ar-H). LR-FAB for
C48H66O6S2 calcd 802.43. Found: 803. G2: Mp: 181–
184°C. 1H NMR (CDCl3, 250 MHz): l 0.88 (m, 12H,
CH2CH3), 1.2–1.8 (m, 80H, CH2), 3.03 (t, J=7.9 Hz, 4H,
SCH2), 3.13 (t, J=7.9 Hz, 4H, SCH2), 3.97 (m, 12H,
OCH3), 7.11 (d, 4H, J=8.5 Hz, Ar-H), 7.58 (d, 4H,
J=8.5 Hz, Ar-H), 7.70 (d, 4H, J=8.5 Hz, Ar-H), 7.80 (s,
2H, Ar-H), 7.83 (s, 4H, Ar-H), 7.94 (d, J=8.5 Hz, 4H,
Ar-H). LR-FAB for C106H134O12S4 calcd 1726.88. Found:
1727.2. G3: Mp: 202–205°C. 1H NMR (CDCl3, 250
MHz): l 0.88 (m, 6H, CH2CH3), 1.2–1.8 (m, 160H, CH2),
3.10 (m, 16H, SCH2), 3.95 (m, 24H, OCH3), 7.10 (m, 8H,
Ar-H), 7.52 (m, 8H, Ar-H), 7.62 (d, 4H, J=8.5 Hz,
Ar-H), 7.68 (d, 4H, J=8.5 Hz, Ar-H), 7.76 (d, 4H, J=8.5
Hz, Ar-H), 7.76 (s, 4H, Ar-H), 7.79 (s, 4H, Ar-H), 7.85
(s, 2H, Ar-H), 7.88 (s, 4H, Ar-H), 7.95 (d, J=8.5 Hz, 4H,
Ar-H). MALDI-TOF for C222H270O24S8 calcd 3575.77.
Found: 3578.31.
7. (a) Devadoss, C.; Bharathi, P.; Moore, J. S. J. Am. Chem.
Soc. 1996, 118, 9635; (b) Poliakov, E. Y.; Chernyak, V.;
Tretiak, S.; Mukamel, S. J. Chem. Phys. 1999, 111,
4158.
8. (a) Wang, P. W.; Liu, Y. J.; Devadoss, C.; Bharathi, P.;
Moore, J. S. Adv. Mater. 1996, 8, 237; (b) Halim, M.;
Pillow, J. N. G.; Samuel, I. D. W.; Burn, P. L. Adv.
Mater. 1999, 11, 371.
9. D´ıez-Barra, E.; Garc´ıa-Mart´ınez, J. C.; Merino, S.; Rey,
R. D.; Rodr´ıguez-Lo´pez, J.; Sa´nchez-Verdu´, P.; Tejeda, J.
J. Org. Chem. 2001, 66, 5664.
10. Peng, Z.; Pan, Y.; Xu, B.; Zhang, J. J. Am. Chem. Soc.
2000, 122, 6619.
11. (a) Prasad, P. N.; Williams, D. J. Introduction to Nonlin-
ear Optical Effects in Molecules and Polymers; Wiley:
New York, 1991; (b) Chemla, D. S.; Zyss, J. Nonlinear
Optical Properties of Organic Molecules and Crystals;
Academic Press: New York, 1987; Vol. 1 and 2; (c)
Dalton, L. R.; Harper, A. W.; Ghosn, G.; Steier, W. H.;
Ziari, M.; Fetterman, H.; Shi, Y.; Mustacich, R. V.; Jen,
A. K.-Y.; Shea, K. J. Chem. Mater. 1995, 7, 1060.
12. (a) Nalwa, H. S.; Watanabe, T.; Miyata, S. Adv. Mater.
1995, 7, 1991; (b) Zyss, J.; Ledoux, I. Chem. Rev. 1994,
94, 77.
16. Wang, J.; Lu, M.; Pan, Y.; Peng, Z. J. Org. Chem., in
press.