Spatially Resolved Derivatization of Solid-Phase-Synthesis Beads with Fluorescent Dendrimers: Creation of Localized Microdomains

Cardona, Claudia M.; Jannach, Stephan H.; Huang, Hao; Itojima, Yukiko; Leblanc, Roger M.; Gawley, Robert E.; Baker, Gary A.; Brauns, Eric B.

doi:10.1002/1522-2675(200210)85:10<3532::aid-hlca3532>3.0.co;2-f

Cited by 15 publications

(5 citation statements)

References 10 publications

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“…However, addition of sulfuric acid to the reaction mixture makes the esterification reaction more efficient. Coupling of the CTV−tris-amine compound with thioctic acid in the presence of HATU and triethylamine afforded the target compound in 67% yield. , We also tried DIC and HOBt as the coupling reagents, but the reaction gave worse yields. The structure and conformation of 1 were confirmed by 1 H and 13 C NMR, MS, and elemental analysis.…”

Section: Resultsmentioning

confidence: 99%

Selective Anion Sensing by a Tris-Amide CTV Derivative: ¹H NMR Titration, Self-Assembled Monolayers, and Impedance Spectroscopy

Zhang

Echegoyen

2005

J. Am. Chem. Soc.

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A hydrogen-bond forming tris(amide) receptor based on cyclotriveratrylene (CTV) was prepared. Self-assembled monolayers (SAMs) of the receptor were formed on gold surfaces. Desorption experiments show a surface coverage of 2.26 x 10(-10) mol/cm(2). (1)H NMR and UV measurements confirm that the receptor exhibits the highest affinity for acetate ions among the anions studied. Electrochemical impedance was used to investigate anion sensing by the SAMs and proved to be an efficient and convenient technique for detecting anions in aqueous solutions. Upon binding acetate anions, the monolayer-modified gold electrodes show a drastic increase of the R(ct) values when Fe(CN)(6)(3-/4-) is used as the redox probe. When the probe was changed to a positively charged one, Ru(NH3)(6)(3+/2+), the R(ct) values decreased monotonically as the acetate concentration was increased, thus confirming the accumulation of negative surface charge upon anion binding. H(2)PO(4-) shows some interference when sensing AcO-. Other monovalent anions such as Cl-, Br-, NO3(-) and HSO4(-) do not bind to the CTV receptor either in solution or on the surfaces.

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Section: Resultsmentioning

confidence: 99%

Selective Anion Sensing by a Tris-Amide CTV Derivative: ¹H NMR Titration, Self-Assembled Monolayers, and Impedance Spectroscopy

Zhang

Echegoyen

2005

J. Am. Chem. Soc.

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“…Polymeric electroluminescent materials have distinct advantages over their inorganic counterparts, including ease of film preparation and color tunability throughout the visible spectrum . Polymers garnering their electroluminescent properties from coumarin moieties have received some interest in both published and patent literature. − Uchida and co-workers patented a series of acrylate-based polymers consisting of a coumarin derivative and N -vinylcarbazole used in the production of an electroluminescent device . They fabricated electroluminescent devices with colors ranging from red to violet by changing the coumarin derivative and the ratio of the number of coumarin groups to the number of N -vinylcarbazole groups in the polymer.…”

Section: 3 Electroluminescence Studiesmentioning

confidence: 99%

Coumarins in Polymers: From Light Harvesting to Photo-Cross-Linkable Tissue Scaffolds

et al. 2004

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“…Hyperbranch dendrimers have been the focus of recent studies pertaining to structural morphology of dendrimers. Cardona and co-workers have reported the synthesis and the photophysical properties of Newkome-type dendrimers with different fluorescent chromophores (fluorophores). A fluorophore when attached to the core provides insight into the physical properties of the molecule as a whole.…”

Section: Introductionmentioning

confidence: 99%

Self-Association of Protected Newkome-Type Second-Generation Dendrimers at Nanomolar Level Concentrations in Aqueous Solution

et al. 2004

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Protected Newkome-type second-generation dendrimers (based on Lin's amine) were synthesized with a pyrene moiety attached to the core. The photophysical property in aqueous solution of the protected dendrimers shows self-association behavior in water. Pyrene excimer emission at 475 nm is observed in water even at very low concentrations of protected dendrimer (ca. 5 × 10-8 M). This emission band is absent in other solvents even up to a concentration of 10-5 M. The corresponding unprotected dendrimer does not show the pyrene excimer fluorescence. The amide of pyrene butyric acid with tert-butylamine shows the formation of excimer, albeit with very low intensity. Quenching studies on the dendrimer with hydrophilic quencher iodide anion (I-) reveal that there is significant quenching of fluorescence intensity in the case of N-tert-butyl-4-pyren-1-ylbutyramide as compared to that of the pyrene-attached second-generation protected dendrimer. This shows that the pyrene moiety in the case of the protected dendrimer is significantly shielded from the surrounding.

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Spatially Resolved Derivatization of Solid-Phase-Synthesis Beads with Fluorescent Dendrimers: Creation of Localized Microdomains

Cited by 15 publications

References 10 publications

Selective Anion Sensing by a Tris-Amide CTV Derivative: ¹H NMR Titration, Self-Assembled Monolayers, and Impedance Spectroscopy

Selective Anion Sensing by a Tris-Amide CTV Derivative: ¹H NMR Titration, Self-Assembled Monolayers, and Impedance Spectroscopy

Coumarins in Polymers: From Light Harvesting to Photo-Cross-Linkable Tissue Scaffolds

Self-Association of Protected Newkome-Type Second-Generation Dendrimers at Nanomolar Level Concentrations in Aqueous Solution

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Spatially Resolved Derivatization of Solid-Phase-Synthesis Beads with Fluorescent Dendrimers: Creation of Localized Microdomains

Cited by 15 publications

References 10 publications

Selective Anion Sensing by a Tris-Amide CTV Derivative: 1H NMR Titration, Self-Assembled Monolayers, and Impedance Spectroscopy

Selective Anion Sensing by a Tris-Amide CTV Derivative: 1H NMR Titration, Self-Assembled Monolayers, and Impedance Spectroscopy

Coumarins in Polymers: From Light Harvesting to Photo-Cross-Linkable Tissue Scaffolds

Self-Association of Protected Newkome-Type Second-Generation Dendrimers at Nanomolar Level Concentrations in Aqueous Solution

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Product

Resources

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Selective Anion Sensing by a Tris-Amide CTV Derivative: ¹H NMR Titration, Self-Assembled Monolayers, and Impedance Spectroscopy

Selective Anion Sensing by a Tris-Amide CTV Derivative: ¹H NMR Titration, Self-Assembled Monolayers, and Impedance Spectroscopy