Extending the limits of precision polymer synthesis: Giant polyphenylene dendrimers in the megadalton mass range approaching structural perfection

Journal of the American Chemical Society

Volumn 135, Issue 11, 2013, Pages 4183-4186

  Nguyen, Thi Thanh Tam ^a,b   Baumgarten, Martin ^a   Rouhanipour, Ali ^a   Räder, Hans Joachim ^a   Lieberwirth, Ingo ^a   Müllen, Klaus ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

^b INSTITUT CHARLES SADRON   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANALYTICAL TOOL; DIELS-ALDER SYNTHESIS; MALDI-TOF MASS SPECTROMETRY; MONODISPERSITY; POLYMER SYNTHESIS; POLYPHENYLENE DENDRIMER; STRUCTURAL PERFECTION; TRANSMISSION ELECTRON;

CHROMOPHORES; DENDRIMERS; MASS SPECTROMETRY; TRANSMISSION ELECTRON MICROSCOPY;

SIZE EXCLUSION CHROMATOGRAPHY;

DENDRIMER; POLYPHENYLENE DENDRIMER; UNCLASSIFIED DRUG;

ACCURACY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHROMATOPHORE; CYCLOADDITION; DESILYLATION; DIELS ALDER REACTION; GEL PERMEATION CHROMATOGRAPHY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MOLECULAR WEIGHT; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; RADIATION ABSORPTION; SYNTHESIS; TRANSMISSION ELECTRON MICROSCOPY; ULTRAVIOLET RADIATION;

EID: 84875461219     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja311430r     Document Type: Article

References (50)

1. Fréchet, J. M. J.; Tomalia, D. A. Dendrimers and Other Dendritic Polymers; Wiley: New York, 2001.
2. Tomalia, D. A.; Christensen, J. B.; Boas, U. Dendrimers, Dendrons and Dendritic Polymers; Cambridge University Press: New York, 2012.
3. Frechet, J. M. Science 1994, 263, 1710
4. Newkome, G. R. M.; Moorefield, C. N.; Vögtle, F. Dendrimers and Dendrons: Concepts, Syntheses, Applications; Wiley-VCH, Weinheim, Germany, 2002.
5. Vögtle, F.; Richardt, G.; Werner, N. Dendrimer Chemistry; Wiley-VCH: Weinheim, Germany, 2009.
6. Zeng, F.; Zimmerman, S. C. Chem. Rev. 1997, 97, 1681
7. Bosman, A. W.; Janssen, H. M.; Meijer, E. W. Chem. Rev. 1999, 99, 1665
8. Designing Dendrimers; Campagna, S.; Ceroni, P.; Puntoriero, F., Eds.; Wiley: Hoboken, NJ, 2012.
9. Tuerp, D.; Nguyen, T. T. T.; Baumgarten, M.; Müllen, K. New J. Chem. 2012, 36, 282
10. Grayson, S. M.; Fréchet, J. M. J. Chem. Rev. 2001, 101, 3819
11. Astruc, D.; Boisselier, E.; Ornelas, C. T. Chem. Rev. 2010, 110, 1857
12. Marchi, E.; Baroncini, M.; Bergamini, G.; Van Heyst, J.; Vögtle, F.; Ceroni, P. J. Am. Chem. Soc. 2012, 134, 15277
13. John, A.; Nachtigall, F. M.; Santos, L. S. Curr. Org. Chem. 2012, 16, 1776
14. Venturi, M.; Ceroni, P. Curr. Top. Electrochem. 2011, 16, 31
15. Wang, R. E.; Costanza, F.; Niu, Y.; Wu, H.; Hu, Y.; Hang, W.; Sun, Y.; Cai, J. J. Controlled Release 2012, 159, 154
16. Walter, M. V.; Malkoch, M. Chem. Soc. Rev. 2012, 41, 4593
17. Caminade, A.-M.; Ouali, A.; Keller, M.; Majoral, J.-P. Chem. Soc. Rev. 2012, 41, 4113
18. Frey, H. Nat. Mater. 2012, 11, 359
19. Astruc, D. Nat. Chem. 2012, 4, 255
20. Abdul, Q. M.; Colderon, M.; Haag, R. In Dendritic Polymers in Oncology: Facts, Features, and Applications; Wiley-VCH: Weinheim, Germany, 2012; pp 513-551.
21. Sadekar, S.; Ghandehari, H. Adv. Drug Delivery Rev. 2012, 64, 571
22. Turrin, C.-O.; Caminade, A.-M. In Unexpected Biological Applications of Dendrimers and Specific Multivalency Activities; Wiley: Chichester, U.K., 2011; pp 485-509.
23. Qin, T.; Wiedemair, W.; Nau, S.; Trattnig, R.; Sax, S.; Winkler, S.; Vollmer, A.; Koch, N.; Baumgarten, M.; List, E. J. W.; Müllen, K. J. Am. Chem. Soc. 2011, 133, 1301
24. Morgenroth, F.; Kubel, C.; Müllen, K. J. Mater. Chem. 1997, 7, 1207
25. Majoral, J.-P.; Caminade, A.-M. Top. Curr. Chem. 1998, 197, 79
26. Miller, T. M.; Neenan, T. X.; Zayas, R.; Bair, H. E. J. Am. Chem. Soc. 1992, 114, 1018
27. Newkome, G. R.; Yao, Z.; Baker, G. R.; Gupta, V. K. J. Org. Chem. 1985, 50, 2003
28. Tomalia, D. A.; Baker, H.; Dewald, J.; Hall, M.; Kallos, G.; Martin, S.; Roeck, J.; Ryder, J.; Smith, P. Macromolecules 1986, 19, 2466
29. van der Made, A. W.; van Leeuwen, P. W. N. M.; de Wilde, J. C.; Brandes, R. A. C. Adv. Mater. 1993, 5, 466
30. Ruiz, J.; Lafuente, G.; Marcen, S.; Ornelas, C.; Lazare, S.; Cloutet, E.; Blais, J.-C.; Astruc, D. J. Am. Chem. Soc. 2003, 125, 7250
31. Xu, Z.; Moore, J. S. Angew. Chem., Int. Ed. Engl. 1993, 32, 1354
32. Moore, J. S.; Xu, Z. Macromolecules 1991, 24, 5893
33. Xu, Z.; Kahr, M.; Walker, K. L.; Wilkins, C. L.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 4537
34. Sartor, V.; Djakovitch, L.; Fillaut, J.-L.; Moulines, F.; Neveu, F.; Marvaud, V.; Guittard, J.; Blais, J.-C.; Astruc, D. J. Am. Chem. Soc. 1999, 121, 2929
35. Jiang, Y.; Lu, Y.-X.; Cui, Y.-X.; Zhou, Q.-F.; Ma, Y.; Pei, J. Org. Lett. 2007, 9, 4539
36. Sun, G.; Guan, Z. Macromolecules 2010, 43, 4829
37. Moore, J. S. Acc. Chem. Res. 1997, 30, 402
38. Clark, C. G.; Wenzel, R. J.; Andreitchenko, E. V.; Steffen, W.; Zenobi, R.; Müllen, K. J. Am. Chem. Soc. 2007, 129, 3292
39. deGennes, P. G.; Hervet, H. J. Phys., Lett. 1983, 44, 351
40. Baumgarten, M.; Qin, T.; Müllen, K. Shape Persistent Polyphenylene-Based Dendrimers. In Designing Dendrimers; Campagna, S.; Ceroni, P.; Puntoriero, F.; Eds.; Wiley: Hoboken, NJ, 2012; pp 121-159.
41. Ornelas, C.; Ruiz, J.; Belin, C.; Astruc, D. J. Am. Chem. Soc. 2009, 131, 590
42. Andreitchenko, E. V.; Clark, C. G.; Bauer, R. E.; Lieser, G.; Müllen, K. Angew. Chem., Int. Ed. 2005, 44, 6348
43. Jackson, C. L.; Chanzy, H. D.; Booy, F. P.; Drake, B. J.; Tomalia, D. A.; Bauer, B. J.; Amis, E. J. Macromolecules 1998, 31, 6259
44. Lartigue, M.-L.; Donnadieu, B.; Galliot, C.; Caminade, A.-M.; Majoral, J.-P.; Fayet, J.-P. Macromolecules 1997, 30, 7335
45. Slany, M.; Bardaji, M.; Casanove, M.-J.; Caminade, A.-M.; Majoral, J.-P.; Chaudret, B. J. Am. Chem. Soc. 1995, 117, 9764
46. Feng, F.; Lee, S. H.; Cho, S. W.; Komurlu, S.; McCarley, T. D.; Roitberg, A. E.; Kleiman, V. D.; Schanze, K. S. Langmuir 2012, 28, 16679
47. Davis, B. L.; Melinger, J. S.; McMorrow, D.; Peng, Z.; Pan, Y. J. Lumin. 2004, 106, 301
48. Aksenov, A. A. B.; Mark, E. J. Am. Soc. Mass Spectrom. 2008, 19, 219
49. Schriemer, D. C.; Li, L. Anal. Chem. 1996, 68, 2721
50. Martin, K.; Spickermann, J.; Räder, H. J.; Müllen, K. Rapid Commun. Mass Spectrom. 1996, 10, 1471