2003
DOI: 10.1021/ja029175u
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Single Side Strapping:  A New Approach to Fine Tuning the Anion Recognition Properties of Calix[4]pyrroles

Abstract: Three calix[4]pyrroles bearing m-orcinol-derived diether straps of different lengths on one side of the tetrapyrrolic core have been synthesized and characterized. Structural information for an analogous diester bridged strapped system reported previously (Yoon, D. W.; Hwang, H.; Lee, C. H. Angew. Chem., Int. Ed. Engl. 2002, 41, 1757-1759) is also provided as are bromide and chloride anion affinities for all four systems determined by Isothermal Titration Calorimetry (ITC) in acetonitrile. Although both sets o… Show more

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Cited by 154 publications
(84 citation statements)
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“…[435] Auch für andere Anionenrezeptoren wurden Stabilisierungsbeiträge durch C-H-Gruppen nachgewiesen. [436] Die C-H-Acidität der Pyrazolringe in 39 reicht aus, um Tetrabutylammoniumchlorid in Aceton mit K = 1.7 10 4 m À1 zu binden, gleichzeitig erfahren die beteiligten C-H-Protonen eine Entschirmung von etwa 1.5 ppm. [437] C-H-Brücken mit Aromaten [438] als Akzeptoren bilden naturgemäß die schwächsten denkbaren Komplexe, wobei Rechnungen einen wesentlichen Beitrag von dispersiven Wechselwirkungen indizieren.…”
Section: Supramolekulare Komplexeunclassified
“…[435] Auch für andere Anionenrezeptoren wurden Stabilisierungsbeiträge durch C-H-Gruppen nachgewiesen. [436] Die C-H-Acidität der Pyrazolringe in 39 reicht aus, um Tetrabutylammoniumchlorid in Aceton mit K = 1.7 10 4 m À1 zu binden, gleichzeitig erfahren die beteiligten C-H-Protonen eine Entschirmung von etwa 1.5 ppm. [437] C-H-Brücken mit Aromaten [438] als Akzeptoren bilden naturgemäß die schwächsten denkbaren Komplexe, wobei Rechnungen einen wesentlichen Beitrag von dispersiven Wechselwirkungen indizieren.…”
Section: Supramolekulare Komplexeunclassified
“…[15,[37][38][39][40][41][42][43][44] Attachment of substituents to CP has also been used to modify the binding properties, and has led to systems capable of binding selectively certain ions or neutral molecules. [45][46][47][48][49][50][51][52][53][54][55][56] A successful example of this latter strategy involved fluorine substitution on the beta-pyrrolic positions of the CP core; the resulting systems (Scheme 1) demonstrate enhanced affinities for small anions such as Cl À , F À , and H 2 PO 4 À . [19,57,58] A number of studies, both theoretical and experimental, have confirmed that calix [4]pyrroles are not preorganized for anion recognition.…”
Section: Introductionmentioning
confidence: 99%
“…One of the merits of the present work is the design and successful synthesis of the dyad having a phthalocyanbine core and the peripheral calixpyrrole. Calixpyrroles and other type of calixarenes are currently attracting considerable interest due to their ability to form complexes with anions or even to form an assembly with anion/cation pairs [10][11][12] . We will show that while absorption spectroscopy does not allow assessing the interaction of the calixpyrrole armed phthalocyanine with halides, electrochemistry and photophysical measurements provide experimental support in favor of complexation of these calixpyrrole-substituted metal phthalocyanines with Cl -and F -with the calixpyrrole units.…”
Section: Introductionmentioning
confidence: 99%