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1.
J Am Chem Soc ; 2023 Nov 02.
Artigo em Inglês | MEDLINE | ID: mdl-37917939

RESUMO

The architecture of self-assembled host molecules can profoundly affect the properties of the encapsulated guests. For example, a rigid cage with small windows can efficiently protect its contents from the environment; in contrast, tube-shaped, flexible hosts with large openings and an easily accessible cavity are ideally suited for catalysis. Here, we report a "Janus" nature of a Pd6L4 coordination host previously reported to exist exclusively as a tube isomer (T). We show that upon encapsulating various tetrahedrally shaped guests, T can reconfigure into a cage-shaped host (C) in quantitative yield. Extracting the guest affords empty C, which is metastable and spontaneously relaxes to T, and the T⇄C interconversion can be repeated for multiple cycles. Reversible toggling between two vastly different isomers paves the way toward controlling functional properties of coordination hosts "on demand".

2.
Chem Commun (Camb) ; 58(21): 3461-3464, 2022 Mar 10.
Artigo em Inglês | MEDLINE | ID: mdl-35064258

RESUMO

We show that the optical properties of indigo carmine can be modulated by encapsulation within a coordination cage. Depending on the host/guest molar ratio, the cage can predominantly encapsulate either one or two dye molecules. The 1 : 1 complex is fluorescent, unique for an indigo dye in an aqueous solution. We have also found that binding two dye molecules stabilizes a previously unknown conformation of the cage.

3.
Commun Chem ; 5(1): 44, 2022 Mar 30.
Artigo em Inglês | MEDLINE | ID: mdl-36697669

RESUMO

Confining molecules within well-defined nanosized spaces can profoundly alter their physicochemical characteristics. For example, the controlled aggregation of chromophores into discrete oligomers has been shown to tune their optical properties whereas encapsulation of reactive species within molecular hosts can increase their stability. The resazurin/resorufin pair has been widely used for detecting redox processes in biological settings; yet, how tight confinement affects the properties of these two dyes remains to be explored. Here, we show that a flexible PdII6L4 coordination cage can efficiently encapsulate both resorufin and resazurin in the form of dimers, dramatically modulating their optical properties. Furthermore, binding within the cage significantly decreases the reduction rate of resazurin to resorufin, and the rate of the subsequent reduction of resorufin to dihydroresorufin. During our studies, we also found that upon dilution, the PdII6L4 cage disassembles to afford PdII2L2 species, which lacks the ability to form inclusion complexes - a process that can be reversed upon the addition of the strongly binding resorufin/resazurin guests. We expect that the herein disclosed ability of a water-soluble cage to reversibly modulate the optical and chemical properties of a molecular redox probe will expand the versatility of synthetic fluorescent probes in biologically relevant environments.

4.
Nanoscale ; 12(16): 8909-8914, 2020 Apr 30.
Artigo em Inglês | MEDLINE | ID: mdl-32266900

RESUMO

Sustainable energy storage devices are required in view of the current demand for environmentally friendly technology. We fabricated a fully recyclable electrochemical double-layer supercapacitor (EDLC), based on multiwalled carbon nanotube (MWCNT) electrodes, an organic nanocrystalline (ONC) dielectric membrane, and an aqueous electrolyte. The entire EDLC device was fabricated and recycled using simple solution processing. The pristine and recycled EDLC devices maintained high stability after 18 000 cycles in cyclic voltammetry testing. Our results advance a concept of sustainable energy storage devices that are easy to fabricate and recycle.

5.
Chemistry ; 23(66): 16782-16786, 2017 Nov 27.
Artigo em Inglês | MEDLINE | ID: mdl-28800185

RESUMO

In the context of drug discovery, novel spirocyclic pyrrolidines have been synthesized in two steps from common three- to seven-membered-ring (hetero)alicyclic ketones. The key transformation is a reaction between an electron-deficient exocyclic alkene and an in situ generated N-benzyl azomethine ylide. The developed method has been used to synthesize the central diamine core of the known antibacterial agents Sitafloxacin and Olamufloxacin.


Assuntos
Antibacterianos/síntese química , Pirrolidinas/química , Compostos de Espiro/química , Antibacterianos/química , Catálise , Reação de Cicloadição , Desenho de Fármacos , Paládio/química , Pirrolidinas/síntese química
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