Self-assembling dendrimers

Science

Volumn 271, Issue 5252, 1996, Pages 1095-1098

  Zimmerman, Steven C ^a   Zeng, Fanwen ^a   Reichert, David E C ^a   Kolotuchin, Sergei V ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID; POLYMER; SOLVENT;

ARTICLE; CHEMISTRY; CHROMATOGRAPHY; HYDROGEN BOND; MACROMOLECULE; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYSICAL CHEMISTRY; SYNTHESIS;

CARBOXYLIC ACIDS; CHEMISTRY, PHYSICAL; CHROMATOGRAPHY; HYDROGEN BONDING; MACROMOLECULAR SUBSTANCES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR WEIGHT; POLYMERS; SOLVENTS;

EID: 0030598465     PISSN: 00368075     EISSN: None     Source Type: Journal    
DOI: 10.1126/science.271.5252.1095     Document Type: Article

References (25)

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11. A preliminary study showing the formation of a hydrogen-bonded 2 1 dendritic aggregate was recently reported [G. R. Newkome, C. N. Moorefield, R Güther, G. R. Baker, Polym Prepr. Am Chem, Soc. Drv. Polym. Chem. 36, 609 (1995)].
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13. 1H NMR to be >95% pure. As further evidence of purity, all dendrimers exhibited a single peak by size exclusion or high-performance liquid chromatographies. All dendrimers up to the fourth generation gave correct fast atom bombardment (FAB) or matrix-assisted laser desorption Ionization (MALDI) mass spectra. Complete synthetic details will be published elsewhere.
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17. This latter result shows that for stable aggregates little retention occurs through specific carboxylic acid-resin contacts, a conclusion firmly supported by the following observations, (i) Most tetraacids 1 had symmetric SEC peaks, whereas analogous non-assembling isophthalic acids showed significant tailing; (ii) the retention times changed minimally with a change in eluent from methylene chloride to toluene to 1:1 hexane-toluene, and (iii) for 1c, the collected peak from SEC contained the same amount as was injected.
18. Because of its high MW, 1d was examined in toiuene on an SEC column with a higher MW range This precluded many direct comparisons with 1 a to 1c.
19. For example, Hawker and Fréchet reported that PS is a reasonable standard for small dendrimers (similar to 4a to 4d), but it underestimates the MW of dendrimers with higher generation numbers [C. J Hawker and J. M. J. Fréchet, J. Am. Chem Soc. 112, 7638 (1990)] Assemblies 1a to 1d are not expected to exhibit similar SEC behavior to dense dertdrimers of high-generation number. The radius of gyration of each aggregate 1a to 1d determined with PS as the standard was close to the aggregate radius determined by molecular modeling A similar finding was reported by Moore and co-workers for covalent dendrimers (5).
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24. P. Roger and P Colonna, Carbohydr. Polym. 21, 83 (1993); M. W. Anthonsen, K. M Vårum, A. M. Hermansson, O. Smidsrod, D. A. Brant, ibid. 25, 13 (1994); M. Mhatre, R. Qian, I. S. Krull, S. Gadam, S M. Cramer, Chromatographia 38, 349 (1994)
25. Supported by National institutes of Health grant GM39782. We thank P. A. Thiessen for assistance with the modeling and J. K. Barbay for help with the synthesis.