Synthetic studies on tetrastilbenylmethane dendrimers: Preparation and optical properties of a second generation dendron

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry

Volumn 42, Issue 4, 2003, Pages 858-862

  Sengupta, Saumitra ^a   Sadhukhan, Subir Kumar ^a  

^a JADAVPUR UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE; DENDRIMER; DIAZONIUM COMPOUND; FUCHSINE; PHOSPHINE DERIVATIVE; STYRENE DERIVATIVE; TETRASTILBENYLMETHANE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE; TRISTILBENYLMETHYLSTYRENE; UNCLASSIFIED DRUG; VINYL TRIMETHYLSILANE;

ARTICLE; CATALYST; HECK REACTION; OPTICAL ROTATION; ROOM TEMPERATURE; SYNTHESIS;

EID: 0038159434     PISSN: 03764699     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (52)

1. (a) Oldham Jr W J, Lachicotte R J & Bazan G C, J Am Chem Soc, 120. 1998, 2987.
2. (b) Wang S, Oldham Jr W J, Hudack Jr R A & Bazan G C, J Am Chem Soc, 122, 2000, 5695.
3. (c) Robinson M R, Wang S & Bazan G C, Adv Mater, 12, 2000, 1701.
4. (a) Fagan P J, Ward M D & Calabrese J C, J Am Chem Soc, 111, 1989, 1698.
5. (b) Constable E C, Eich O, Housecroft C E & Johnstone L A, J Chem Soc, Chem Commun, 1998, 2661.
6. (c) Constable E C, Eich O & Housecroft C E, J Chem Soc, Dalton Trans, 1999, 1363.
7. (d) Constable E C, Eich O, Housecroft C E & Rees D C, Inorg Chim Acta, 300-302, 2000, 158.
8. (a) Yeh H -C, Chan L -H, Lee R -H & Chen C -T, SPIEInt Soc Opt Eng, 4105, 2000, 348;
9. (b) Yeh H -C, Lee R -H, Chan L -H, Lin T -Y J, Chen C -T, Balasubramaniam E & Tao Y -T, Chem Mater, 13, 2001, 2788;
10. (c) Aujard I, Baltaze J -P, Baudin J -B, Cogné E, Ferrage F, Jullien L, Perez E, Prévost V, Qian L H & Rucl O, J Am Chem Soc, 123, 2001, 8177;
11. (d) Zhao H, Tanjutco C & Thayumanavan S, Tetrahedron Lett, 42, 2001, 4421;
12. (e) Sengupta S & Sadhukhan S K, Tetrahedron Lett, 43, 2002, 3521.
13. Roncali J, J Mater Chem, 9, 1999, 1875 and references cited therein.
14. (a) Hoskins B F & Robson R, J Am Chem Soc, 112, 1990, 1546;
15. (b) Simard M, Su D & Wuest J D, J Am Chem Soc, 113, 1991, 4696;
16. (c) Venkataraman D, Lee S, Moore J S, Zhang P, Hirsch K A, Gardner G B, Covey A C & Prentice C L, Chem Mater, 8, 1996, 2030;
17. (d) Reddy D S, Craig D C & Desiraju G R, J Am Chem Soc, 118, 1996, 4090;
18. (e) Galoppini E & Gilardi R, J Chem Soc, Chem Commun, 1999, 173;
19. (f) Jetti R K R, Xue F, Mak T C W & Nangia A, J Chem Soc, Perkin Trans 2, 2000, 1223.
20. (a) Mongin O & Gossauer A, Tetrahedron, 53, 1997, 6835;
21. (b) Maus M, De R, Lor M, Weil T, Mitra S, Wiesler U M, Herrmann A, Hofkens J, Vosch T, Müllen K & De Schryver F C, J Am Chem Soc, 123, 2001, 7668;
22. (c) Weil T, Wiesler U M, Herrmann A, Bauer R, Hofkens J, De Schryver F C & Müllen K, J Am Chem Soc, 123, 2001, 8101;
23. (d) Sengupta S & Pal N, Tetrahedron Lett, 43, 2002, 3517.
24. (a) Zimmerman T J, Freundel O, Gompper R & Muller T J J, Eur J Org Chem, 2000, 3305;
25. (b) Langhals H, Ismael R & Yuruk O, Tetrahedron, 56, 2000, 5435;
26. (c) Langhals H, Wagner C & Ismael R, New J Chem, 25, 2001, 1047;
27. (d) Rathore R, Burns C L & Deselnicu M I, Org Lett, 3, 2001, 2887;
28. (e) Zimmerman T J & Muller T J J, Eur J Org Chem, 2002, 2269;
29. (f) Zimmerman T J & Muller T J J, Synthesis, 2002, 1157;
30. (g) Kramer, C S, Zimmerman T J, Sailer M & Muller T J J, Synthexis, 2002, 1163.
31. (a) Grimsdale A C, Bauer R, Weil T, Tchebotareva N, Wu J, Watson M, Mullen K, Synthesis, 2002, 1229;
32. (b) Zhu L, Tang H, Harima Y, Yamashita K, Hirayama D, Aso Y & Otsubo T, J Chem Soc, Chem Commun, 2001, 1830;
33. (c) Sengupta S, Sadhukhan S K & Singh R S, Indian J Chem, 41B, 2002, 642.
34. (a) Sengupta S & Sadhukhan S K, Organometallics, 20, 2001, 1889;
35. (b) Sengupta S & Sadhukhan S K, Tetrahedron Lett, 42, 2001, 3659.
36. Sengupta S & Sadhukhan S K, Carbohydr Res, 332, 2001, 215.
37. (a) Burroughes J H, Bradley D D C, Brown A R, Marks R N, McKay K, Friend R H, Burn P L, Holmes A B, Nature, 347, 1990, 539;
38. (b) Kraft A, Grimsdale A C & Holmes A B, Angew Chem, Int Ed Engl, 37, 1998, 402;
39. (c) Martin R E & Diederich F, Angew Chem, Int Ed Engl, 38, 1999, 1350;
40. (d) Mitschke U & Bäurele P, J Mater Chem, 10, 2000, 1471.
41. Su D & Menger F M, Tetrahedron Lett, 38, 1997, 1485.
42. For styrene synthesis via Heck reaction of haloarenes with vinyl silanes, see (a) Jefferey T, Tetrahedron Lett, 40, 1999, 1673; (b) Mowery M E & DeShong P, J Org Chem, 64, 1999, 1684.
43. For styrene synthesis via Heck reaction of haloarenes with vinyl silanes, see (a) Jefferey T, Tetrahedron Lett, 40, 1999, 1673; (b) Mowery M E & DeShong P, J Org Chem, 64, 1999, 1684.
44. Kikukawa K, Wada F & Matsuda T, J Organomet Chem, 270, 1984, 277.
45. 3, 300 MHz): δ 5.22 (d, J= 11 Hz, 1H), 5.72 (d, J= 18 Hz, 1H), 6.69 (dd, J = 11, 18 Hz, 1H), 7.157.31 (m, 19H).
46. Sengupta S & Sadhukhan S K, J Chem Soc, Perkin Trans 1, 1999, 2235.
47. (a) de Meijere A & Meyer F E, Angew Chem, Int Ed Engl, 33, 1994, 2379;
48. (b) Jeffery T In Advances in MetalOrganic Chemistry; Liebeskind L S, Ed.; JAI Press: Greenwich, C T, 1996; vol. 5, p. 153;
49. (c) Beletskaya I P & Cheprakov A V, Chem Rev. 100, 2000, 3009.
50. 3, 300 MHz) 7: δ 2.40 (s, 9H), 6.72 (dd. J = 8.4, 2.1 Hz, 3H), 7.18 (d, J = 2.1 Hz, 3H), 7.74 (d, J= 8.4 Hz, 3H). 8: δ 2.38 (s, 9H), 2.76 (s, 1H), 6.99 (d, J= 16.1 Hz, 3H), 7.11 (d, J = 7.8 Hz, 3H), 7.19 (s, 3H), 7.237.36 (m, 12H), 7.487.54 (m, 9H). 9: δ 2.35 (s, 9H), 3.64 (br, 2H). 6.59 (d, J = 8.7 Hz, 2H), 6.99 (d, J = 16.2 Hz, 3H), 7.04 (d. J = 8.7 Hz, 2H), 7.077.15 (m, 6H), 7.227.28 (m, 6H), 7.30 (d, J = 16.2 Hz, 3H), 7.35 (t, J = 7.2 Hz, 3H), 7.36 (d, J = 7.2 Hz, 3H), 7.477.52 (m, 6H), 10b: δ 2.35 (s. 9H), 5.23 (d, J = 11 Hz, 1H), 5.73 (d, J = 17.4 Hz, 1H), 6.70 (dd, J = 11, 17.4 Hz, IH), 7.00 (d, J = 16.2 Hz, 3H), 7.057.11 (m, 6H), 7.227.28 (m, 9H), 7.307.38 (m, 10H), 7.50 (d, J = 7 Hz, 6H).
51. Meier H, Angew Chem, Int Ed Engl, 31, 1992, 1399.
52. The molar absortivity of tetraphenylmethane is 2020 compared to 212 for benzene. For constructive excitonic couplings, see Kasha M, Rawls H R, Ashraf El-Bayoumi M, Pure Appl Chem, 11, 1965, 371.