Synthesis, Characterization, and Guest−Host Properties of Inverted Unimolecular Dendritic Micelles
10.1021/ja954207h
Crossref journal-article
American Chemical Society (ACS)
Journal of the American Chemical Society (316)
Authors 6
  1. S. Stevelmans (first)
  2. J. C. M. van Hest (additional)
  3. J. F. G. A. Jansen (additional)
  4. D. A. F. J. van Boxtel (additional)
  5. E. M. M. de Brabander-van den Berg (additional)
  6. E. W. Meijer (additional)
References 26 Referenced 239
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  21. . Typical preparation and characterization of an alkyl-modified dendrimer, DAB-dendr-(palmitoyl)8:  To a solution of 2.5 g DAB-dendr-(NH2)8(1 equiv, 3.3 mmol) in 50 mL THF, 5.00 g triethylamine and 8.56 g palmitoyl chloride (1.10 equiv, 28.6 mmol) were added. After the mixture stirred for 20 h at room temperature, the solvent was evaporated. The mixture was heated under reflux in 50 mL of diethyl ether for 30 min and filtered, to remove excess palmitoyl chloride. To the residue, a solution of 2 g Na2CO3in 50 mL H2O was added, and the mixture was heated under reflux for 6 h, in order to remove residual ammonium salts and to deprotonate the dendrimers. The mixture was filtered, the residue was driedin vacuoat 40 °C, and the product was obtained as a white/yellow solid material (yield 76%).1H-NMR (CDCl3):  δ 0.90 (t, CH3), 1.18−1.75 (m, CH2−CH3+ CH2−CH2−CH2), 2.17 (t, NHCO−CH2), 2.40 (m, CH2−N−(CH2)2), 3.28 (q, CH2−NHCO), 6.95 (t, NHCO) ppm.13C-NMR (CDCl3):  δ 14.10 (CH3), 22.69 (CH2−CH3), 24.87 (N−CH2−CH2−CH2−CH2−N + N−CH2−CH2−CH2−N), 25.96 (NHCO−CH2−CH2), 27.09 (N−CH2−CH2−CH2−NHCO), 29.37− 29.73 (CH2−(CH2)n−CH2), 31.93 (CH2−CH2−CH3), 36.75 (NHCO−CH2), 37.93 (CH2−NHCO), 51.64 (N−CH2−CH2−CH2−NHCO), 52.20 (N−CH2−CH2−CH2−CH2−N + N−CH2−CH2−CH2−N), 173.59 (NHCO) ppm. IR:  amide N−H stretch 3300.2 cm-1, sec. amide N−H stretch 3083.8 cm-1, C−H sat. 2918.1 cm-1, sec. amide CO 1638.9 cm-1, N−H bend 1560.0 cm-1. DSC:  phase transition at 74.3 °C. MALDI-TOF:  measurement of DAB-dendr-(NHCOC15)8:  2683 g/mol, calcd 2678 g/mol.
  22. This phenomenon was observed for reactions between a 2- 3- and 4-fold excess of DAB-dendr-(NH2)4-64based on the number of primary amine end groupsand palmitoyl and oleyl chloride. The workup procedure with the Na2CO3solution resulted in separation between water-soluble DAB-dendr-(NH2)4-64and modified DAB-dendr-(NHCOCn)4-64. Both products isolated were unambiguously identified with IR and NMR spectroscopies, and the melting points of the amidated products resembled those of the products made by using equimolar amounts of reactants. For experimental details, see the supporting information.
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Dates
Type When
Created 23 years, 1 month ago (July 26, 2002, 1:02 a.m.)
Deposited 3 years, 10 months ago (Oct. 13, 2021, 4:22 p.m.)
Indexed 3 weeks, 2 days ago (Aug. 7, 2025, 4:59 p.m.)
Issued 29 years, 7 months ago (Jan. 1, 1996)
Published 29 years, 7 months ago (Jan. 1, 1996)
Published Online 29 years ago (Aug. 7, 1996)
Published Print 29 years, 7 months ago (Jan. 1, 1996)
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@article{Stevelmans_1996, title={Synthesis, Characterization, and Guest−Host Properties of Inverted Unimolecular Dendritic Micelles}, volume={118}, ISSN={1520-5126}, url={http://dx.doi.org/10.1021/ja954207h}, DOI={10.1021/ja954207h}, number={31}, journal={Journal of the American Chemical Society}, publisher={American Chemical Society (ACS)}, author={Stevelmans, S. and van Hest, J. C. M. and Jansen, J. F. G. A. and van Boxtel, D. A. F. J. and de Brabander-van den Berg, E. M. M. and Meijer, E. W.}, year={1996}, month=jan, pages={7398–7399} }