Poly(propylene imine) dendrimers functionalized with stilbene or 1,4-distyrylbenzene chromophores

Tetrahedron

Volumn 63, Issue 46, 2007, Pages 11429-11435

  Schulz, Andrea ^a   Meier, Herbert ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

Crosslinking; Dendrimers; Photochemistry

Indexed keywords

1,4 DISTYRYLBENZENE; BENZENE DERIVATIVE; DENDRIMER; IMINE; NANOPARTICLE; POLY(PROPYLENE IMINE); POLYPROPYLENE; SCHIFF BASE; STILBENE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; FLUORESCENCE; HORNER REACTION; HYDROGENATION; IRRADIATION; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; OLIGOMERIZATION; PHOTOCHEMISTRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 34848850411     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.08.064     Document Type: Article

References (100)

1. See for example:
2. Newkome G.R., Moorefield C.N., and Vögtle F. Dendrimers and Dendrons: Concepts, synthesis, Applications (2001), Wiley-VCH, Weinheim
3. Fréchet J.M.J., and Tomalia D.A. Dendrimers and Other Dendritic Polymers (2001), Wiley, New York, NY
4. Soomro S.A., Schulz A., and Meier H. Tetrahedron 62 (2006) 8089
5. Ong W., and McCarley R.L. Org. Lett. 7 (2005) 1287
6. Vögtle F., Fakhrnabavi H., Lukin O., Mueller S., Friedhofen J., and Schalley C.A. Eur. J. Org. Chem. 22 (2004) 4717
7. Vicinelli V., Ceroni P., Maestri M., Lazzari M., Balzani V., Lee S.-K., van Heyst J., and Vögtle F. Org. Biomol. Chem. 2 (2004) 2207
8. Ceroni P., Vicinelli V., Maestri M., Balzani V., Gorka M., Lee S.-K., Dragut P., and Vögtle F. Collect. Czech. Chem. Commun. 68 (2003) 1541
9. Frerot E., Herbal K., and Herrmann A. Eur. J. Org. Chem. 6 (2003) 967
10. Lee J.W., Ko Y.H., Park S.-H., Yamaguchi K., and Kim K. Angew. Chem. 113 (2001) 769
11. Angew. Chem., Int. Ed. 40 (2001) 746
12. Baars M.W.P.L., Kleppinger R., Koch M.H.J., Yeu S.-L., and Meijer E.W. Angew. Chem. 112 (2000) 1341
13. Angew. Chem., Int. Ed. 39 (2000) 1285
14. Baars M.W.P.L., Soentjens S.H.M., Fischer H.M., Peerlings H.W.I., and Meijer E.W. Chem.-Eur. J. 4 (1998) 2456
15. Smith G., Chen R., and Mapolie S. J. Organomet. Chem. 673 (2003) 111
16. Volkova N.N., Tarasov E.V., Kodess M.I., Van Meervelt L., Dehaen W., and Bakulev V.A. Org. Biomol. Chem. 1 (2003) 4030
17. Christensen J.B., Nielsen M.F., van Haare J.A.E.H., Baars M.W.P.L., Janssen R.A.J., and Meijer E.W. Eur. J. Org. Chem. 11 (2001) 2123
18. Klein G., Robertus J.M., Bosman A.W., Feiters M.C., Meijer E.W., and Nolte R.J.M. Chem.-Eur. J. (1999) 65
19. Heuzé K., Méry D., Gauss D., Blais J.-C., and Astruc D. Chem.-Eur. J. 10 (2004) 3936
20. Jones J.W., Bryant W.S., Bosman A.W., Janssen R.A.J., Meijer E.W., and Gibson H.W. J. Org. Chem. 68 (2003) 2385
21. Engel G.D., and Gode L.H. Chem.-Eur. J. 8 (2002) 4319
22. Stephan H., Spies H., Johannsen B., Gloe K., Gorka M., and Vögtle F. Eur. J. Inorg. Chem. 11 (2001) 2957
23. Boas U., Karlsson A., de Waal B.F.M., and Meijer E.W. J. Org. Chem. 66 (2001) 2136
24. Saltiel J., and Sun Y.-P. In: Dürr H., and Bouas-Laurent H. (Eds). Photochromism, Molecules and Systems (2003), Elsevier, Amsterdam
25. Liu R.S.H. Acc. Chem. Res. 34 (2001) 555
26. Görner H., and Kuhn H.J. Adv. Photochem. 19 (1995) 1
27. Arai T., and Tokumaru K. Chem. Rev. 93 (1993) 23
28. Meier H. Angew. Chem. 104 (1992) 1425
29. Angew. Chem., Int. Ed. Engl. 31 (1992) 1399
30. Waldeck D.H. Chem. Rev. 91 (1991) 415
31. Mazzucato U., and Momicchioli F. Chem. Rev. 91 (1991) 1679
32. Selected newer publications:
33. Onagi H., Belke C.J., Easton C.J., and Lincoln S.F. Chem.-Eur. J. 9 (2003) 5978
34. Tokunaga Y., Akasaka K., Hisada K., Shimomura Y., and Kakuchi S. Chem. Commun. (2003) 2350
35. Gracia H. Pure Appl. Chem. 75 (2003) 1085
36. Stanier C.A., Alderman S.J., Claridge T.D.W., and Anderson H.L. Angew. Chem. 114 (2002) 1847
37. Angew. Chem., Int. Ed. 41 (2002) 1769
38. Jin S.-H., Kim S.-H., and Gal Y.-S. J. Polym. Sci., Part A: Polym. Chem. 39 (2001) 4025
39. Sànchez C., Villacampa B., Alcalà R., Martinez C., Oriol L., Piñol M., and Serrano J.L. Chem. Mater. 11 (1999) 2804
40. Strashnikova N., Papper V., Parkhomyuk P., Likhtenshtein G.I., Ratner V., and Marks R. J. Photochem. Photobiol., A: Chem. 122 (1999) 133
41. Grabchev I., and Philipova T. Angew. Makromol. Chem. 263 (1998) 1
42. Meier H., and Lehmann M. In: Nalwa H.S. (Ed). Encyclopedia of Nanoscience and Nanotechnology Vol. 10 (2004), American Scientific, Stevenson Ranch, USA 95
43. Watanabe S., Ikegami M., Nagaheta R., and Arai T. Bull. Chem. Soc. Jpn. 80 (2007) 586
44. Miura Y., Momotake A., Shinohara Y., Wahadoszamen M., Nishimura Y., and Arai T. Tetrahedron Lett. 48 (2007) 639
45. Nishimura Y., Kamada M., Ikegami M., Nagahata R., and Arai T. J. Photochem. Photobiol., A: Chem. 178 (2006) 150
46. Momotake A., Hayakawa J., Nagahata R., and Arai T. Bull. Chem. Soc. Jpn. 77 (2004) 1195
47. Momotake A., and Arai T. J. Photochem. Photobiol., C: Photochem. Rev. 5 (2004) 1
48. Gutierrez-Nava M., Accorsi G., Masson P., Armaroli N., and Nierengarten J.-F. Chem.-Eur. J. 10 (2004) 5076
49. Momotake A., Uda M., and Arai T. J. Photochem. Photobiol., A: Chem. 158 (2003) 7
50. Tatewaki H., Mizutani T., Hayakawa J., Arai T., and Terazima M. J. Phys. Chem. A 107 (2003) 6515
51. Hayakawa J., Momotake A., and Arai T. Chem. Commun. (2003) 94
52. Hayakawa J., Momotake A., and Arai T. Chem. Lett. 32 (2003) 1008
53. Uda M., Momotake A., and Arai T. Org. Biomol. Chem. 1 (2003) 1635
54. Uda M., Mizutani T., Hayakawa J., Momotake A., Ikegami M., Nagahata R., and Arai T. J. Photochem. Photobiol. 76 (2002) 596
55. Imai M., and Arai T. Tetrahedron Lett. 43 (2002) 5265
56. Mizutani T., Ikegami M., Nagahata R., and Arai T. Chem. Lett. (2001) 1014
57. Drobizhev M., Karotki A., Kruk M., Dzenis Y., Rebane H., Meng F., Nickel E., and Spangler C.W. Proc. SPIE-Int. Soc. Opt. Eng. 5211 (2003) 63
58. Spangler C.W., Suo Z., Drobizhev M., Karotki A., and Rebane H. NATO Science Series, II: Math., Phys., Chem. 100 (2003) 139
59. Beavington R., Frampton M.J., Lupton J.M., Burn P.L., and Samuel I.D.W. Adv. Funct. Mater. 13 (2003) 211
60. Pålsson L.-O., Beavington R., Frampton M.J., Lupton J.M., Magennis S.W., Markham J.P.J., Pillow J.N.G., Burn P.L., and Samuel I.D.W. Macromolecules 35 (2002) 7891
61. Guldi D.M., Swartz A., Luo C., Gómez R., Segura J.L., and Martín N. J. Am. Chem. Soc. 124 (2002) 10875
62. Langa F., Gómez-Escalonilla J.M., Díez-Barra E., García-Martínez J.C., de la Hoz A., Rodriguez-López J., González-Cortés A., and López-Arza V. Tetrahedron Lett. 42 (2001) 3435
63. Segura J.L., Gómez R., Martín N., Luo C., Swartz A., and Guldi D.M. Chem. Commun. (2001) 707
64. Burn P.L., Beavington R., Frampton M.J., Pillow J.N.G., Halim M., Lupton J.M., and Samuel I.D.W. Mater. Sci. Eng., B: Solid-State Mater. Adv. Technol. 85 (2001) 190
65. Lupton J.M., Samuel I.D.W., Beavington R., Burn P.L., and Bässler H. Synth. Met. 116 (2001) 357
66. Adv. Mater. 13 (2001) 258
67. Díez-Barra E., García-Martínez J.C., Rodriguez-López J., Goméz R., Segura J.L., and Martín N. Org. Lett. 2 (2000) 3651
68. Halim M., Pillow J.N.G., Samuel I.D.W., and Burn P.L. Adv. Mater. 11 (1999) 371
69. Pillow J.N.G., Halim M., Lupton J.M., Burn P.L., and Samuel I.D.W. Macromolecules 32 (1999) 5985
70. Díez-Barra E., García-Martínez J.C., and Rodriguez-López J. Tetrahedron Lett. 40 (1999) 8181
71. Rosenfeldt S., Karpuk E., Lehmann M., Meier H., Lindner P., Harnau L., and Ballauff M. Chem. Phys. Chem. 7 (2006) 2097
72. Lehmann M., Köhn C., Meier H., Renker S., and Oelhof A. J. Mater. Chem. 16 (2006) 141
73. Soomro S.A., Benmouna R., Berger R., and Meier H. Eur. J. Org. Chem. (2005) 3586
74. Uda M., Momotake A., and Arai T. Tetrahedron Lett. 46 (2005) 3021
75. Momotake A., and Arai T. Polymer 45 (2004) 5369
76. Lehmann M., Fischbach I., Spiess H.W., and Meier H. J. Am. Chem. Soc. 126 (2004) 772
77. Segura J.L., Goméz R., Martín N., and Guldi D.M. Org. Lett. 3 (2001) 2645
78. Meier H., Lehmann M., and Kolb U. Chem.-Eur. J. 6 (2000) 2462
79. Petermann R., Schnorpfeil C., Lehmann M., Fetten M., and Meier H. J. Inf. Recording 25 (2000) 259
80. Meier H., Lehmann M., Schnorpfeil C., and Fetten M. Mol. Cryst. Liq. Cryst. 352 (2000) 85
81. Lehmann M., Schartel B., Hennecke M., and Meier H. Tetrahedron 55 (1999) 13377
82. Meier H., and Lehmann M. Angew. Chem. 110 (1998) 666
83. Angew. Chem., Int. Ed. 37 (1998) 643
84. Deb S.K., Maddux T.M., and Yu L. J. Am. Chem. Soc. 119 (1997) 9079
85. Schenning A.P.H.J., Peeters E., and Meijer E.W. J. Am. Chem. Soc. 122 (2000) 4489
86. Such procedures for the extension of stilbenoid chains have often been successfully used; see for example Refs. 14-16.
87. Armaroli N., Accorsi G., Clifford J.N., Eckert J.-F., and Nierengarten J.-F. Chem. Asian J. 1 (2006) 564
88. Gutiérrez-Nava M., Jaeggy M., Nierengarten H., Masson P., Guillon D., Van Dorsselaer A., and Nierengarten J.-F. Tetrahedron Lett. 44 (2003) 3039
89. 3J=12.1 Hz and a singlet for the protons on the alkoxy-substituted benzene ring at 6.38 ppm. The latter signal is particularly useful for the detection of traces of the (Z)-isomer.
90. Meier H. Angew. Chem. 117 (2005) 2536
91. Angew. Chem., Int. Ed. 44 (2005) 2482
92. Lewis F.D., Wu T., Burch E.L., Bassani D.M., Yang J.-S., Schneider S., Jäger W., and Letsinger R.L. J. Am. Chem. Soc. 117 (1995) 8785
93. Song X., Geiger C., Farahat M., Perlstein J., and Whitten D.G. J. Am. Chem. Soc. 119 (1997) 12481
94. Lewis F.D. Acc. Chem. Res. 19 (1986) 401 and references therein
95. Meier H., Kretzschmann H., and Lang M. J. Prakt. Chem. 336 (1994) 297
96. Mamane V., Hannen P., and Fürstner A. Chem.-Eur. J. 10 (2004) 4556
97. Mervič M., and Ghera E. J. Org. Chem. 45 (1980) 4720
98. Sandros K., Sundahl M., Wennerström O., and Norinder U. J. Am. Chem. Soc. 112 (1990) 3082
99. Careful drying in the vacuum did not lead to complete evaporation of water. Therefore exact elemental analyses could not be obtained for the dendrimers 9, 10, 11, and 14.
100. A correct mass spectrum, which contains the molecular ion, could not be obtained (FD MS, ESI, MALDI-TOF).