A binol-strapped calix[4]pyrrole as a model chirogenic receptor for the enantioselective recognition of carboxylate anions.

نویسندگان

  • Hidekazu Miyaji
  • Seong-Jin Hong
  • Seung-Doo Jeong
  • Dae-Wi Yoon
  • Hee-Kyung Na
  • Jooyeon Hong
  • Sihyun Ham
  • Jonathan L Sessler
  • Chang-Hee Lee
چکیده

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Calix[4]pyrroles such as meso-octamethylcalix[4]pyrrole 1 have been extensively studied as anion and ion-pair receptors over recent years. Subsequently ‘strapped’ calix[4]pyrroles, pioneered by Lee and Sessler, have been synthesised that contain a single linker between distal meso-positions. These compounds have increased 15 affinity for anions relative to the parent macrocycle. Recently there ...

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Photoinduced electron transfer in a supramolecular triad produced by porphyrin anion-induced electron transfer from tetrathiafulvalene calix[4]pyrrole to Li(+)@C60.

Binding of a porphyrin carboxylate anion () to tetrathiafulvalene calix[4]pyrrole (TTF-C4P) results in electron transfer from TTF-C4P to Li(+)@C60 to produce the charge-separated state (1/TTF-C4P˙(+)/Li(+)@C60˙(-)) in benzonitrile. Upon photoexcitation of , photoinduced electron transfer from the triplet excited state of to TTF-C4P˙(+) occurs to produce the higher energy charge-separated state ...

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Reconciling Experiment and Theory in the Use of Aryl-Extended Calix[4]pyrrole Receptors for the Experimental Quantification of Chloride–π Interactions in Solution

In this manuscript we consider from a theoretical point of view the recently reported experimental quantification of anion-π interactions (the attractive force between electron deficient aromatic rings and anions) in solution using aryl extended calix[4]pyrrole receptors as model systems. Experimentally, two series of calix[4]pyrrole receptors functionalized, respectively, with two and four ary...

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Ion pair-induced conformational motion in calix[4]arene-strapped calix[4]pyrroles.

In order to understand the still-poorly understood interplay between calix[4]arene conformations and cation and anion recognition in multicomponent systems, the ion pair receptors 1 and 2 were synthesized. In solution and in the solid state, the calix[4]arene subunit of receptor 1 adopts a cone conformation, while that of 2 interconverts between the cone and the partial cone conformation. These...

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Sensing of antipyretic carboxylates by simple chromogenic calix[4]pyrroles.

We present a simple, two- or three-step method for the synthesis of chromogenic octamethylcalix[4]pyrrole-based (OMCP) sensors for anions. Electrophilic aromatic substitution allows for converting the pyrrole moieties of OMCP into a dye. The formation of a sensor-anion complex results in partial charge transfer and a dramatic change in color. The absorption (UV-vis) and NMR titration experiment...

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عنوان ژورنال:
  • Angewandte Chemie

دوره 46 14  شماره 

صفحات  -

تاریخ انتشار 2007