From Large Furan-Based Calixarenes to Calixpyrroles and Calix[n]furan[m]pyrroles: Syntheses and Structures

Cafeo, Grazia; Kohnke, Franz H.; Torre, Giovanna Loredana La; White, Andrew J. P.; Williams, David J.

doi:10.1002/(sici)1521-3773(20000417)39:8<1496::aid-anie1496>3.0.co;2-i

Cited by 104 publications

(36 citation statements)

References 18 publications

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“…Since the submission of this manuscript there have been considerable advances in the synthesis of expanded or “higher‐order” calix[ n ]pyrrole macrocycles ( n >4) 164, 165. Very recently, Kohnke and co‐workers found that meso ‐dodecamethylcalix[6]pyrrole 152 , meso ‐dodecamethylcalix[3]furan[3]pyrrole 150 , and meso ‐dodecamethylcalix[2]furan[4]pyrrole 151 may be prepared from meso ‐dodecamethylcalix[6]furan 146 (Scheme ) 166. Reaction of the calix[6]furan 146 with meta ‐chloroperbenzoic acid ( m ‐CPBA) followed by zinc/AcOH opens either some or all of the furan rings to afford a mixture of macrocycles 147 – 149 containing α , δ ‐diketone functionalities.…”

Section: Addendummentioning

confidence: 99%

Anion Recognition and Sensing: The State of the Art and Future Perspectives

Beer

Gale

2001

Angew. Chem. Int. Ed.

3,457

653

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Anion recognition chemistry has grown from its beginnings in the late 1960s with positively charged ammonium cryptand receptors for halide binding to, at the end of the millennium, a plethora of charged and neutral, cyclic and acyclic, inorganic and organic supramolecular host systems for the selective complexation, detection, and separation of anionic guest species. Solvation effects and pH values have been shown to play crucial roles in the overall anion recognition process. More recent developments include exciting advances in anion‐templated syntheses and directed self‐assembly, ion‐pair recognition, and the function of anions in supramolecular catalysis.

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Section: Addendummentioning

confidence: 99%

Anion Recognition and Sensing: The State of the Art and Future Perspectives

Beer

Gale

2001

Angew. Chem. Int. Ed.

3,457

653

View full text Add to dashboard Cite

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“…Seit Einreichen des Manuskripts wurden erhebliche Fortschritte bei der Synthese von erweiterten Calix[ n ]heteroaren‐Makrocyclen höherer Ordnung ( n >4) erzielt 164, 165. So synthetisierten Kohnke et al meso ‐Dodecamethylcalix[6]pyrrol 152 , meso ‐Dodecamethylcalix[3]furan[3]pyrrol 150 und meso ‐Dodecamethylcalix[2]furan[4]pyrrol 151 ausgehend von meso ‐Dodecamethylcalix[6]furan 146 (Schema ) 166. Durch Umsetzung von 146 mit meta ‐Chlorperbenzoesäure ( m ‐CPBA) und anschließend mit Zinc/AcOH werden einige oder alle Furanringe geöffnet, und man erhält ein Gemisch aus den Makrocyclen 147 – 149 mit unterschiedlich vielen α , δ ‐Diketonfunktionalitäten.…”

Section: Addendumunclassified

Erkennung und Nachweis von Anionen: gegenwärtiger Stand und Perspektiven

2001

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Die Chemie der Anionenerkennung hat sich seit ihren Anfängen in den späten sechziger Jahren des 20. Jahrhunderts stark entwickelt. Anfangs waren nur positiv geladene Ammonium‐Cryptanden als Rezeptoren für Halogenid‐Ionen bekannt. Nun, am Ende des Millenniums, sind eine Vielzahl geladener und neutraler, cyclischer und acyclischer, anorganischer und organischer supramolekularer Wirte für die selektive Komplexierung, den Nachweis und die Trennung anionischer Gastmoleküle verfügbar. Bei der Anionenerkennung spielen Solvatationseffekte und der pH‐Wert eine entscheidende Rolle. In jüngerer Zeit wurden wichtige Fortschritte bei Synthesen mit anionischen Templaten, der durch Anionen gesteuerten Selbstorganisation, der Ionenpaarerkennung und der Funktion von Anionen bei der supramolekularen Katalyse erzielt.

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“…It is also worth noting that similar Paal-Knorr type reactions with poly(1,4-diketone)s often leave isolated ketones between two generated aromatic rings 24 . The alternating 1,3-and 1,4-diketone system favours full conversion of 1,4-diketone subunits to aromatic rings via Paal-Knorr synthesis 25 in high yields, keeping only the terminal acetyl groups intact.…”

Section: Resultsmentioning

confidence: 99%

Oligoacetylacetones as shapable carbon chains and their transformation to oligoimines for construction of metal-organic architectures

et al. 2018

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Flexible chain-like molecules can adopt various conformations, but fabrication of complex and higher-order architectures by chain networking or coiling is still a difficult task in organic chemistry. As the degree of freedom increases, the large entropy loss impedes conformation and orientation fixing. Here we report oligo (3,3-dimethylpentane-2,4-dione)s as flexible and shapable carbon chains with many carbonyl groups for chemical modification. Polycarbonylated chains of various lengths are synthesized by terminal-selective silylation and oxidative coupling reactions using silver(I) oxide. We use reactions of 1,3-diketones and 1,4diketones to reduce the chain length and to induce favourable conformations. When the chains are treated with hydrazine, all the carbonyl groups are converted to imine groups, resulting in the formation of multidentate ligands. Finally, a two-dimensional sheet-like structure and a cylindrical assembly are generated by respectively networking and coiling the carbon chains, with the aid of metal coordination.

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From Large Furan-Based Calixarenes to Calixpyrroles and Calix[n]furan[m]pyrroles: Syntheses and Structures

Cited by 104 publications

References 18 publications

Anion Recognition and Sensing: The State of the Art and Future Perspectives

Anion Recognition and Sensing: The State of the Art and Future Perspectives

Erkennung und Nachweis von Anionen: gegenwärtiger Stand und Perspektiven

Oligoacetylacetones as shapable carbon chains and their transformation to oligoimines for construction of metal-organic architectures

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