Dendrimers Derived from 1 → 3 Branching Motifs

Newkome, George R.; Shreiner, Carol D.

doi:10.1021/cr900341m

Cited by 331 publications

(186 citation statements)

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“…Prior to attaching the peripherald endrons, the addition of mercaptopropionic acid led to the key electrophilic buildingb lock 1,w hereas the addition of aminoethanethiol led to an ucleophilic buildingb lock 2.U sing standard peptide coupling reagents,w ef inally attached the water-solubilising dendrons with an increasing number of TEG chains per peptide side arm. Newkomed endron D 3 , [13] with three TEG chains, was coupled to core 1 to obtain 1.D 3 .D endrons D 4 and D 8 , based on the 2,2-bis-methylolpropionic acid (bis-MPA) dendritic scaffold and appended with four and eight TEG chains,r espectively,w ere coupled to molecule 2 to obtaint he amphiphilic dendrimers 2.D 4 and 2.D 8 .…”

Section: Synthesismentioning

confidence: 99%

Steric Constraints Induced Frustrated Growth of Supramolecular Nanorods in Water

Appel

Fuchs

Tyrrell

et al. 2015

Chemistry A European J

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Document VersionPublisher's PDF, also known as Version of Record (includes final page, issue and volume numbers)Please check the document version of this publication:• A submitted manuscript is the author's version of the article upon submission and before peer-review. There can be important differences between the submitted version and the official published version of record. People interested in the research are advised to contact the author for the final version of the publication, or visit the DOI to the publisher's website.• The final author version and the galley proof are versions of the publication after peer review.• The final published version features the final layout of the paper including the volume, issue and page numbers. Link to publication Citation for published version (APA):Appel, R., Fuchs, J., Tyrrell, S. M., Korevaar, P. A., Stuart, M. C. A., Voets, I. K., ... Besenius, P. (2015). Steric constraints induced frustrated growth of supramolecular nanorods in water. Chemistry -A European Journal, 21(52), 19257-19264. DOI: 10.1002/chem.201503616 General rights Copyright and moral rights for the publications made accessible in the public portal are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights.• Users may download and print one copy of any publication from the public portal for the purpose of private study or research.• You may not further distribute the material or use it for any profit-making activity or commercial gain • You may freely distribute the URL identifying the publication in the public portal ? Take down policyIf you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. Ilja K. Voets, [d, f] Monika Schçnhoff, [c] and Pol Besenius* [a, b] Abstract: Au nique example of supramolecular polymerisation in waterb ased on monomers with nanomolara ffinities, which yield rod-like materials with extraordinarily high thermodynamic stability, yet of finite length, is reported. A small libraryo fc harge-neutral dendritic peptide amphiphiles was prepared,w ith ab ranched nonaphenylalanine-based core that was conjugated to hydrophilic dendrons of variable steric demand. Below ac ritical size of the dendron,the monomers assemble into nanorod-like polymers,w hereas for larger dendritic side chainsf rustratedg rowth into near isotropic particles is observed.T he supramolecular morphologies observed by electron microscopy,X -ray scattering and diffusion NMR spectroscopy studies are in agreement with the mechanistic insights obtained from fitting polymerisationp rofiles:n on-cooperative isodesmic growth leads to degrees of polymerisation that matcht he experimentally determined nanorod contour lengths of close to 70 nm. The reportedd esignsf or aqueous self-assembly into well-defined anisotropic particles has promising potentialf or biomedical applicat...

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Section: Synthesismentioning

confidence: 99%

Steric Constraints Induced Frustrated Growth of Supramolecular Nanorods in Water

Appel

Fuchs

Tyrrell

et al. 2015

Chemistry A European J

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“…T o date, dendrimers and metal nanoparticles (NPs) have been largely involved in materials science including nanomedicine, photonics and supramolecular chemistry [1][2][3][4][5] , and in particular metallodendrimers and dendrimercontaining NPs 2-4,6-11 have been efficiently designed for catalysis [2][3][4] , photophysics [7][8][9][10][11] and sensing [9][10][11][12][13] . Redox-stable metallodendrimers are a specific class of materials allowing redox anion recognition, sensing [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16] and biosensing 14,15 that have been used essentially with ferrocene derivatives [12][13][14][15] .…”

mentioning

confidence: 99%

Metallodendrimers in three oxidation states with electronically interacting metals and stabilization of size-selected gold nanoparticles

et al. 2014

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Metallodendrimers containing redox-robust centres may have applications in molecular redox recognition, sensing, biosensing and catalysis. So far, however, no metallodendrimer is known in several oxidation states. Here we report metallodendrimers with two electronically communicating iron centres that are stable and isolated in both the Fe II and Fe III oxidation states, and in addition as class-II mixed-valent Fe II Fe III complexes. These dendrons are branched to arene-centred dendrimer cores either by Sonogashira coupling or 'click' reactions. The latter reaction involves the introduction of intradendritic 1,2,3-triazolyl ligands, which allows investigation of the selective role of these ligands in intradendritic Au III coordination and Au 0 nanoparticle stabilization. As a result, and using the various metallodendrimers with different oxidation states, small Au 0 nanoparticles are intradendritically stabilized by the triazole ligands, whereas with the related non-'click' dendrimers large Au 0 nanoparticles are formed outside the dendrimers and stabilized by a group of dendrimers.

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“…Acetate-terminated polyester dendrimers with 1,1,1-tris(p-hydroxyphenyl)ethane (9) as a core were synthesized from generation one to four (M w : 906, 1,856, 3,754, and 7,549 g/mol) by adding the above dendrons in a convergent growth approach (Scheme 13). The simplicity of the 1 H NMR and 13 C NMR spectra and elemental analyses suggest that pure and monodisperse dendrimers were obtained. However, attempts to selectively remove the acetate groups in order to obtain the corresponding hydroxyl-terminated dendrimers for further chemical surface modification were not successful due to the lack of selectivity in the hydrolysis of the acetate and ester groups.…”

Section: The Use Of 22-bis(hydroxymethyl)propanoic Acid-derived Dendmentioning

confidence: 99%

“…As shown in Scheme 14, reacting the fourth generation dendron (12) with 9 gave a fourth generation polyester dendrimer in good yield. The periphery of the hydroxyl-terminated polyester dendrimer was then functionalized using reactions of its hydroxyl groups with various acid chlorides (benzoyl, octanoyl, and palmitoyl chloride) in the presence of TEA and DMAP in CH 2 Cl 2 to give high yields of monodisperse dendrimers, according to 1 H and 13 C NMR spectra, size exclusion chromatography, and elemental analyses of the products. Scheme 14.…”

Section: Scheme 12mentioning

confidence: 99%

Polyester Dendrimers

Twibanire

Grindley

2012

Polymers

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Polyester dendrimers have been comprehensively reviewed starting from their first synthesis in the early 1990s by Hawker and Fréchet. Polyester dendrimers have attracted and continue to attract extensive interest because they are comparatively easy to make and because, whenever they have been tested, they have been found to be non-toxic. A number of different strategies for their synthesis have been examined and the methods employed for formation of the ester bond during dendrimer assembly have been summarized. The newest approaches, including the use of bifunctional orthogonally reacting dendrons and accelerated synthesis have been surveyed.

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Dendrimers Derived from 1 → 3 Branching Motifs

Cited by 331 publications

References 1,180 publications

Steric Constraints Induced Frustrated Growth of Supramolecular Nanorods in Water

Steric Constraints Induced Frustrated Growth of Supramolecular Nanorods in Water

Metallodendrimers in three oxidation states with electronically interacting metals and stabilization of size-selected gold nanoparticles

Polyester Dendrimers

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