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1.
J Am Chem Soc ; 140(13): 4705-4711, 2018 04 04.
Artículo en Inglés | MEDLINE | ID: mdl-29485275

RESUMEN

Single-molecule surface-enhanced Raman spectroscopy (SERS) offers new opportunities for exploring the complex chemical and biological processes that cannot be easily probed using ensemble techniques. However, the ability to place the single molecule of interest reliably within a hot spot, to enable its analysis at the single-molecule level, remains challenging. Here we describe a novel strategy for locating and securing a single target analyte in a SERS hot spot at a plasmonic nanojunction. The "smart" hot spot was generated by employing a thiol-functionalized cucurbit[6]uril (CB[6]) as a molecular spacer linking a silver nanoparticle to a metal substrate. This approach also permits one to study molecules chemically reluctant to enter the hot spot, by conjugating them to a moiety, such as spermine, that has a high affinity for CB[6]. The hot spot can accommodate at most a few, and often only a single, analyte molecule. Bianalyte experiments revealed that one can reproducibly treat the SERS substrate such that 96% of the hot spots contain a single analyte molecule. Furthermore, by utilizing a series of molecules each consisting of spermine bound to perylene bisimide, a bright SERS molecule, with polymethylene linkers of varying lengths, the SERS intensity as a function of distance from the center of the hot spot could be measured. The SERS enhancement was found to decrease as 1 over the square of the distance from the center of the hot spot, and the single-molecule SERS cross sections were found to increase with AgNP diameter.

2.
J Am Chem Soc ; 139(22): 7432-7435, 2017 06 07.
Artículo en Inglés | MEDLINE | ID: mdl-28538099

RESUMEN

We report here a synthetic ion channel developed from a shape-persistent porphyrin-based covalent organic cage. The cage was synthesized by employing a synthetically economical dynamic covalent chemistry (DCC) approach. The organic cage selectively transports biologically relevant iodide ions over other inorganic anions by a dehydration-driven, channel mechanism as evidenced by vesicle-based fluorescence assays and planar lipid bilayer-based single channel recordings. Furthermore, the organic cage appears to facilitate iodide transport across the membrane of a living cell, suggesting that the cage could be useful as a biological tool that may replace defective iodide channels in living systems.

3.
Angew Chem Int Ed Engl ; 54(45): 13241-4, 2015 Nov 02.
Artículo en Inglés | MEDLINE | ID: mdl-26305107

RESUMEN

The porphyrin boxes (PB-1 and PB-2), which are rationally designed porous organic cages with a large cavity using well-defined and rigid 3-connected triangular and 4-connected square shaped building units are reported. PB-1 has a cavity as large as 1.95 nm in diameter and shows high chemical stability in a broad pH range (4.8 to 13) in aqueous media. The crystalline nature as well as cavity structure of the shape-persistent organic cage crystals were intact even after complete removal of guest molecules, leading to one of the highest surface areas (1370 m(2) g(-1)) among the known porous organic molecular solids. The size of the cavities and windows of the porous organic cages can be modulated using different sized building units while maintaining the topology of the cages, as illustrated with PB-2. Interestingly, PB-2 crystals showed unusual N2 sorption isotherms as well as high selectivity for CO2 over N2 and CH4 (201 and 47.9, respectively at 273 K at 1 bar).

4.
J Org Chem ; 77(1): 707-12, 2012 Jan 06.
Artículo en Inglés | MEDLINE | ID: mdl-22103681

RESUMEN

An efficient regioselective protocol for the C-C bond formation by the unexpected α,α-diarylation of aromatic ketones with unactivated arenes in the presence of selenium dioxide and boron trifluoride etherate has been developed. The generality and functional tolerance of this protocol is demonstrated by the synthesis of a series of triarylethanones.

5.
Chem Commun (Camb) ; 55(42): 5930-5933, 2019 May 21.
Artículo en Inglés | MEDLINE | ID: mdl-31049491

RESUMEN

Fluorescent macromolecules were developed for intracellular labeling in live cells. Coupling rigid rod phenyleneethynylene trimers with flexible amphiphilic diamines via the imine-bond formation chemistry yielded rigid-flexible [2+2] macromolecules showing nucleic acid selectivity and nontoxicity in live cells.


Asunto(s)
Alquinos/química , Éteres/química , Compuestos Macrocíclicos/química , Ácidos Nucleicos/química , Polímeros/química , Células HeLa , Humanos , Espectroscopía de Protones por Resonancia Magnética
6.
Chem Commun (Camb) ; 51(45): 9313-6, 2015 Jun 07.
Artículo en Inglés | MEDLINE | ID: mdl-25958824

RESUMEN

A new type of solid lithium-ion conducting electrolytes prepared by incorporation of Li(+) ions into a cucurbit[6]uril (CB[6])-based organic molecular porous solid shows high Li(+) ion conductivity (∼10(-4) S cm(-1)) and mobility (transference numbers, tLi(+) = 0.7-0.8). In addition, the solid electrolytes show excellent, thermally stable performance even after several temperature cycles.

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