Dendrimer disassembly in the gas phase: A cascade fragmentation reaction of fréchet dendrons

Chemistry - A European Journal

Volumn 15, Issue 29, 2009, Pages 7139-7149

  Baytekin, Bilge ^a   Tank Bavtekin, H ^a   Hahn, Uwe ^b   Reckien, Werner ^c   Kirchner, Barbara ^c   Schalley, Christoph A ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^c UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

Dendrimers; Fragmentation mechanisms; Gas phase reactions; Mass spectrometry

Indexed keywords

COLLISION-INDUCED DISSOCIATION; DENDRONS; DIFFERENT MECHANISMS; EXPERIMENTAL EVIDENCE; FOCAL POINTS; FRAGMENTATION MECHANISMS; FRAGMENTATION REACTIONS; GAS-PHASE REACTIONS; GASPHASE; OH GROUP; POSITIVE MODE; QUATERNARY AMMONIUM IONS;

AMINES; AMMONIUM COMPOUNDS; BROMINE COMPOUNDS; DISSOCIATION; ELECTROSPRAY IONIZATION; FOCUSING; IONIZATION OF GASES; MASS SPECTROMETERS; MASS SPECTROMETRY; PHASE INTERFACES; POSITIVE IONS;

DENDRIMERS;

DENDRIMER; ION;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; GAS; TANDEM MASS SPECTROMETRY;

DENDRIMERS; GASES; IONS; MOLECULAR STRUCTURE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY;

EID: 67650603910     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900403     Document Type: Article

References (115)

1. For recent reviews, see: a) G. R. Newkome, C. N. Moorefield, F. Vögtle, Dendritic Molecules: Concepts, Synthesis, Perspectives, Wiley-VCH, Weinheim, 1996.
2. b) F. Zeng, S. C. Zimmerman, Chem. Rev. 1997, 97, 1681-1712.
3. c) A. Archut, F. Vögtle, Chem. Soc. Rev. 1998, 27, 233-240.
4. d) D. K. Smith, F. Diederich, Chem. Eur. J. 1998, 4, 1353-1361.
5. e)M. Fischer, F. Vögtle, Angew. Chem. 1999, 111, 934-955;
6. Angew. Chem. Int. Ed. 1999, 38, 884-905.
7. f) A.W. Bosman, H. M. Jansen, E. W. Meijer, Chem. Rev. 1999, 99, 16651688.
8. g) G. R. Newkome, E. He, C. N. Moorefield, Chem. Rev. 1999, 99, 1689-1746.
9. h) J.-F. Nierengarten, Chem. Eur. J. 2000, 6, 36673670.
10. i) A. D. Schlüter, J. P. Rabe, Angew. Chem. 2000, 112, 860880;
11. Angew. Chem. Int. Ed. 2000, 39, 864-883.
12. j) G. R. Newkome, C. N. Moorefield, F. Vögtle, Dendrimers and Dendrons. Concepts, Syntheses, Applications, Wiley-VCH, Weinheim, 2001.
13. k) R. Haag, Chem. Eur. J. 2001, 7, 327-335.
14. S. Hecht, J. M. J. Fréchet, Angew. Chem. 2001, 113, 76-94; Angew. Chem. Int. Ed. 2001, 40, 74-91.
15. m) J. M. J. Fréchet, D. A. Tomalia, Dendrimers and other dendritic polymers, Wiley, New York. 2001.
16. n) S. M. Grayson, J. M. J. Fréchet, Chem. Rev. 2001, 101, 3819-3868.
17. o) G. R. Newkome, C. D. Schreiner, Polymer 2008, 49, 1-113.
18. p) F. Vögtle, G. Richardi, N. Werner, Dendritische Moleküle: Konzepte, Synthese, Eigenschaften, Anwendungen, Teubner, Wiesbaden 2007;
19. Dendrimer Chemistry: Concepts, Syntheses, Properties, Applications, Wiley-VCH, Weinheim 2009.
20. J. Denning, Top. Curr. Chem. 2003, 225, 621-672.
21. a) M. Venturi, S. Serroni, A. Juris, S. Campagna, V. Balzani, Top. Curr. Chem 1998, 197, 193-228.
22. b) V. Balzani, P. Ceroni, M. Maestri, C. Saudan, V. Vicinelli, Top. Curr. Chem. 2003, 228, 159-191.
23. D. A. Tomalia, Aldrichimica Acta 2004, 37, 39-57.
24. a) R. J. Amir, N. Pessah, M. Shamis, D. Shabat, Angew. Chem. 2003, 115, 4632-4637;
25. Angew. Chem. Int. Ed. 2003, 42, 4494-4499.
26. b)F.M. H. de Groot, C. Albrecht, R. Koekkoek, P.H. Beusker, H. W. Sheeren, Angew. Chem. 2003, 115, 4628-4632,
27. Angew Chem. Int. Ed. 2003, 42, 4490-4494.
28. c) S. Li, M. L. Szalai, R. M. Kevwitch, D. V. McGrath, J. Am. Chem. Soc. 2003, 125, 10516-10517. Review.
29. d) D. Shabat, J. Polym. Sci A 2006, 44, 1569-1578.
30. D. Schubert, M. Corda, O. Lukin, B. Brusilowskij, E. Fiskin, C. A. Schalley, Eur. J. Org. Chem. 2008, 4148-4156, and references therein.
31. Selected examples: a) M. C. Coen, K. Lorenz, J. Kressler, H. Frey, R. Mülhaupt, Macromolecules 1996, 29, 8069-8076.
32. b) L. Shu, A. D. Schlüter, C. Ecker, N. Severin, J. P. Rabe, Angew. Chem. 2001, 113, 4802-4805;
33. Angew. Chem. Int. Ed. 2001, 40, 4666-4669.
34. c)J. Li, D. R. Swanson, D. Qin, H. M. Brothers, L. T. Piehler, D. A. Tomalia, D. J. Meier, Langmuir 1999, 15, 7347-7350.
35. d) H.-J. van Manen, T. Auletta, B. Dordi, H. Schönherr, G. J. Vancso, F. C. J. M. van Veggel, D. N. Reinhoudt, Adv. Funct. Mater. 2002, 12, 811-818.
36. e) F. Würthner, V. Stepanenko, A. Sautter, Angew. Chem. 2006, 118, 19731976;
37. Angew. Chem. Int. Ed. 2006, 45, 1939-1942.
38. f) R. Bauer, D. Liu, A. V. Heyen, F. D. Schryver, S. D. Feyter, K. Müllen, Macromolecules 2007, 40, 4753-4761.
39. g) H. T. Baytekin, M. Sahre, A. Rang, M. Engeser, A. Schulz, C. A. Schalley, Small 2008, 4, 1823-1834.
40. h) Review: A. D. Schlüter, J. P. Rabe, Angew. Chem. 2000, 112, 860880;
41. Angew. Chem. Int. Ed. 2000, 39, 864-883.
42. C. A. Schalley, B. Baytekin, H. T. Baytekin, M. Engeser, T. Felder, A. Rang, J. Phys. Org. Chem. 2006, 19, 479-490.
43. Representative examples for defect analysis by mass spectrometry:
44. a) C. J. Hawker, J. M. J. Fréchet, J. Am. Chem. Soc. 1990, 112, 76387647.
45. b)M. Liu, J.M.J. Fréchet, Polym. Bull. 1999, 43, 379-386.
46. c) E. K. Wolter, M.J. Cloninger, Org. Lett. 2002, 4, 7-10.
47. d) G. D. Engel, L. H. Gade, Chem. Eur. J. 2002, 8, 4319-4329.
48. e) W. Zhang, S. E. Tichy, L. M. Pérez, G. C. Maria, P. A. Lindahl, E. E. Simanek, J. Am. Chem. Soc. 2003, 125, 5086-5094.
49. f) S. C. Zimmerman, I. Zharov, M. S. Wendland, N. A. Rakow, K. S. Suslick, J. Am. Chem. Soc. 2003, 125, 13504-13518.
50. g) A. Dirksen, U. Hahn, F. Schwanke, M. Nieger, J. N. H. Reek, F. Vögtle, L. De Cola, Chem. Eur. J. 2004, 10, 2036-2047.
51. a) C. G. Juo, L. L. Shiu, C. K. F. Shen, T. Y. Luh, G. R. Her, Rapid Commun. Mass Spectrom. 1995, 9, 604.
52. b) G. Coullerez, H. J. Mathieu, S. Lundmark, M. Malkoch, H. Magnusson, A. Huit, Surf. Interface Anal. 2003, 35, 682 - 692.
53. See, for example: a) T. Kawaguchi, K. L. Walker, C. L. Wilkins, J. S. Moore, J. Am. Chem. Soc. 1995, 117, 2159-2165.
54. b) B. L. Schwartz, A. L. Rockwood, R. D. Smith, D. A. Tomalia, R. Spindler, Rapid Commun. Mass Spectrom. 1995, 9, 1552-1555.
55. c) J. W. Leon, M. Kawa, J.M.J. Fréchet, J. Am. Chem. Soc. 1996, 118, 8847-8859.
56. d) M. S. Wendland, S. C. Zimmerman, J. Am. Chem. Soc. 1999, 127, 1389-1390.
57. e) P.B. Rheiner, D. Seebach, Chem. Eur. J. 1999, 5, 3221-3236.
58. f) L. Bu, W. K. Nonidez, J. W Mays, N. B. Tan, Macromolecules 2000, 33, 4445-4452.
59. g) L. Zhou, D. H. Russell, M. Zhao, R. M. Crooks, Macromolecules 2001, 34, 3567-3573.
60. h) H. Chen, M. He, X. Cao, X. Zhou, J. Pei, Rapid Commun. Mass Spectrom. 2004, 18, 367-370.
61. Selected examples: a) G. J. Kallos, D. A. Tomalia, D. M. Hedstrand, S. Lewis, J. Zhou, Rapid Commun. Mass Spectrom. 1991, 5, 383386.
62. b) J. C. Hummelen, J. L. J. van Dongen, E. W Meijer, Chem. Eur. J. 1997, 3, 1489-1493.
63. c) L. P. Tolic, G. A. Anderson, R. D. Smith, H. M. Brothers II, R. Spindler, D. A. Tomalia, Int. J. Mass Spectrom. 1997, 165, 405-418.
64. d) U. Puapaiboon, R. T. Taylor, Rapid Commun. Mass Spectrom. 1999, 13, 508-515.
65. e) S. Watanabe, M. Sato, S. Sakamoto, K. Yamaguchi, M. Iwamura, J. Am. Chem. Soc. 2000, 722, 12588-12589.
66. f) S. M. Cohen, S. Petoud, K. N. Raymond, Chem. Eur. J. 2001, 7, 272-279.
67. g) Y. Rio, G. Accorsi, H. Nierengarten, J.-L. Rehspringer, B. Hönerlage, G. Kopitkovas, A. Chugreev, A. Van Dorsselaer, N. Armaroli, J.-F. ierengarten, New J. Chem. 2002, 26, 1146-1154.
68. h) A. T. Iavarone, E. R. Williams, J. Am. Chem. Soc. 2003, 125, 2319-2327.
69. i) M. Luostarinen, T. Laitinen, C. A. Schalley, K. Rissanen, Synthesis 2004, 255-262.
70. B. Baytekin, N. Werner, F. Luppertz, M. Engeser, J. Brüggemann, S. Bitter, R. Henkel, T. Felder, C. A. Schalley, Int. J. Mass Spectrom. 2006, 249, 138-148.
71. a) J.-C. Blais, C.-O. Turrin, A.-M, Caminade, J.-P. Majorai, Anal. Chem. 2000, 72, 5097-5105
72. b)T. Felder, C.A. Schalley, H. Fakhrnabavi, O. Lukin, Chem. Eur. J. 2005, 11, 5625-5636.
73. a) J.-W. Weener, J. L. J. Dongen, E. W. Meijer, J. Am. Chem. Soc. 1999, 121, 10346-10355.
74. b) U. Puapaiboon, R. T. Taylor, J. Jainhuknan, Rapid Commun. Mass Spectrom. 1999, 13, 516-520.
75. c) S. Koster, M. C. Duursma, X. Guo, R. A. T. M. van Benthem, C. G. de Koster, J. J. Boon, R. M. A. Heeren, J. Macromol. Chem. 2002, 37, 792-802.
76. d) A. Adhiya, C. Wesdemiotis, Int. J. Mass Spectrom. 2002, 214, 75-88.
77. e) H. Neubert, K. A. Knights, Y. R. de Miguel, D. A. Cowan, Macromolecules 2003, 36, 8297-8303.
78. f) S. Koster, M. C. Duursma, J. J. Boon, R. M. A. Heeren, S. Ingemann, R. A. T. M. van Benthem, C. G. de Koster, J. Am. Soc. Mass Spectrom. 2003, 14, 332-341.
79. g) M. He, S. A. McLuckey, Rapid Commun. Mass Spectrom. 2004, 18, 960-972.
80. Some selected examples for MS-detected self-assembled dendrimers: a) P. S. Corbin, L. J. Lawless, Z. Li, Y. Ma, M. J. Witmer, S. C. Zimmerman, Proc. Natl. Acad. Sci USA 2002, 99, 5099-5104.
81. b) H.-J. van Manen, F. C. J. M. van Veggel, D. N. Reinhoudt, Top. Curr. Chem. 2001, 217, 121-162.
82. a) W. Ong, A. E. Kaifer, Angew. Chem. 2003, 115, 2214-2217;
83. Angew. Chem. Int. Ed. 2003, 42, 2164-2167.
84. b) T. Yamada, M. Ge, H. Shinohara, K. Kimura, S. Mashiko, Chem. Phys. Lett. 2003, 379, 458-465.
85. c)M. A. C. Broeren, J. L. J. van Dongen, M. Pittelkow, X B. Christensen, M. H. P. van Genderen, E. W. Meijer, Angew. Chem. 2004, 116, 3641-3646;
86. Angew. Chem. Int. Ed. 2004, 43, 35573562.
87. C. J. Hawker, J. M. J. Fréchet, J. Chem. Soc. Chem. Commun. 1990, 1010-1013.
88. M. Meot-Ner (Mautner), Chem. Rev. 2005, 105, 213-284.
89. The synthesis, isolation and characterization of Fréchet endrimers with triethylammonium at the focal point has been described earli- er: Z. Bo, L. Zhang, Z. Wang, X. Zhanh, J. Shen, Mater. Sci. Eng. C 1999, 10, 165-1.70.
90. a) C. A. Schalley, C. Verhaelen, F. G. Klärner, U. Hahn, F. Vögtle, Angew. Chem. 2005, 117, 481-485;
91. Angew. Chem. Int. Ed. 2005, 44, 477-480.
92. b) V. Balzani, H. Bandmann, P. Ceroni, C. dansante, U. Hahn, F.-G. Klärner, U. Müller, W. M. Müller, C. Verhaelen, V. Vicinelli, F. Vögtle, J. Am. Chem. Soc. 2006, 128, 637-648.
93. -1 according to the Coulomb law.
94. For reviews, see: a) C. Lifshitz, Acc. Chem. Res. 1994, 27, 138-144. Also, see:
95. b) I. Howe, F. W McLafferty, J. Am. Chem. Soc. 1971, 93, 99-105.
96. c)A. Siegel, J. Am. Chem. Soc. 1974, 96, 1251-1252.
97. d) J. C. Traeger, R. G. McLoughlin, J. Am. Chem, Soc. 1977, 99, 7351-7352.
98. e) G Cone, M. J. S. Dewar, D. Landman, J. Am. Chem. Soc. 1977, 99, 372-376.
99. f) F. W McLafferty, F. M. Bockhoff, Org. Mass Spectrom. 1979, 14, 181-184.
100. g) J. H. Moon, J. C. Choe, M. S. Kim, J. Phys. Chem. A 2000, 104, 458-463.
101. h) M. Malow, M. Penno, K.-M. Weitzel. J. Phys. Chem. A 2003, 107, 10625-10630.
102. T. D. Fridgen, J. Troe, A. A. Viggiono, A. J. Midey, S. Williams, T. B. McMahon, J. Phys. Chem. A 2004, 108, 5600-5609.
103. a) D. Kuck, W. Bäther, H.-F. Grützmacher, J. Am. Chem. Soc. 1979, 101, 7154-7157.
104. b) D. Kuck, W. Bäther, H.-F. Grützmacher, Int. J. Mass Spectrom. Ion Processes 1985, 67, 75-91.
105. E. Buhleier, W. Wehner, F. Vögtle, Synthesis 1978, 155-158.
106. The following articles report the syntheses which have been used: a) O. Trapp, G. Trapp, J. W. Kong, U. Hahn, F. Vögtle, V. Schurig, Chem. Eur. J. 2002, 8, 3629-3634.
107. b) U. Hahn, A. Kaufmann, M. Nieger, O. Julinek, M. Urbanova, F. Vögtle, Eur. J. Org. Chem. 2006, 1237-1244.
108. c) U. Herrmann, T. Jonischkeit, J. Bargon, U. Hahn, Q. Y. Li, C. A. Schalley, E. Vogel, F. Vögtle, Anal. Bioanal. Chem. 2002, 372, 611-614.
109. d) P. Ceroni, V. Vicinelli, M. Maestri, V. Balzani, W M. Müller, U. Müller, U. Hahn, F. Osswald, F. Vögtle, New J. Chem. 2001, 25, 989-993.
110. e) R. Toba, J. M. Quintela, C. Peinador, E. Román, A. E. Kaifer, Chem. Commun. 2001, 857-858.
111. f) T. H. Ghaddar, J. F. Wishart, D. W Thompson, J. K. Whitesell, M. A. Fox, J. Am. Chem. Soc. 2002, 124, 8285-8289.
112. R. Ahlrichs, M. Bär, M. Häser, H. Horn, C. Kölmel, Chem. Phys. Lett. 1989, 762, 165-169. For the current version, see: http:// www.turbomole.de.
113. a) A. D. Becke, Phys. Rev. A 1988, 38, 3098-3100.
114. b) A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
115. The turbomole basis set library is available via anonymous ftp from ftp://ftp.chemie.uni.-k.arl.sruhe.de/pub/basen.