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3 article(s) from Gaeta, Carmine

Supramolecular approaches to mediate chemical reactivity

Pablo Ballester,
Qi-Qiang Wang and
Carmine Gaeta

Beilstein J. Org. Chem. 2022, 18, 1463–1465, doi:10.3762/bjoc.18.152

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Editorial

Published 14 Oct 2022

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Multiple threading of a triple-calix[6]arene host

Veronica Iuliano,
Roberta Ciao,
Emanuele Vignola,
Carmen Talotta,
Patrizia Iannece,
Margherita De Rosa,
Annunziata Soriente,
Carmine Gaeta and
Placido Neri

Beilstein J. Org. Chem. 2019, 15, 2092–2104, doi:10.3762/bjoc.15.207

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Graphical Abstract

Figure 1: Sketch of the currently known prototypical examples of handcuff-derived architectures.

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Figure 2: Chemical drawing of the known bis-calix[6]arene 1 and its handcuff pseudorotaxane architectures 3²⁺...

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Scheme 1: Synthesis of triple-calix[6]arene host 6.

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Scheme 2: Formation of the 7⁺ [Graphic 2] 6, (7⁺)₂6, (7⁺)₃6 pseudorotaxane architectures by multiple-threading of 6 with 7⁺...

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Figure 3: (Bottom) Portion of the ESI-FT-ICR mass spectrum of 7⁺ [Graphic 2] 6. (Top a–c) Significant portions of: (a) ¹H ...

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Figure 4: ¹H NMR titration of 6 with 7⁺·TFPB^– (CDCl₃ , 298 K, 600 MHz). Significant portions of the ¹H NMR sp...

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Figure 5: ESI-FT-ICR-MS and HR-ESI-FT-ICR-CID mass spectrum of (7⁺)₂ [Graphic 2] 6.

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Figure 6: Different views of the minimized structures of (7⁺)₃ [Graphic 2] 6 obtained by molecular mechanics calculations.

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Scheme 3: Formation of the 4⁺ [Graphic 2] 6, (4⁺)₂6, (4⁺)₃6 pseudorotaxane architectures by multiple-threading of 6 with 4⁺...

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Figure 7: (a–d) ¹H NMR titration of 6 with 4⁺·TFPB⁻ (CDCl₃, 298 K, 600 MHz). Significant portions of the ¹H N...

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Figure 8: Different views of the minimized structures of (4⁺)₃ [Graphic 2] 6 obtained by molecular mechanics calculations.

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Figure 9: (Top) Possible endo-benzyl and endo-alkyl stereoisomers obtainable by directional threading of cali...

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Figure 10: (Left) HR-ESI-FT-ICR mass spectrum of 8⁺ [Graphic 2] 6. (Right) HR-ESI-FT-ICR-CID mass spectrum of (8⁺)₂6.

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Figure 11: (a–d) ¹H NMR titration of 6 with 8⁺·TFPB⁻ (CDCl₃ , 298 K, 600 MHz). Significant portions of the ¹H ...

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Letter

Published 03 Sep 2019

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Calix[6]arene-based atropoisomeric pseudo[2]rotaxanes

Carmine Gaeta,
Carmen Talotta and
Placido Neri

Beilstein J. Org. Chem. 2018, 14, 2112–2124, doi:10.3762/bjoc.14.186

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Graphical Abstract

Figure 1: Cartoon representation of the chiral rotaxane of the Goldup group [15,16] (I and I*) and of the chiral pse...

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Figure 2: Cartoon representation of the rotaxane sequence isomers reported by Leigh [17] (III and IV) and of the ...

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Figure 3: The possible 8 discrete conformations of a calix[6]arene macrocycle [26].

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Figure 4: Diastereoisomeric pseudorotaxanes obtained by threading a directional calixarene wheel with directi...

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Scheme 1: Synthesis of threads 2⁺ and 3⁺. Reagents and conditions: a) hexamethyldisilazane, LiClO₄, 30 min, 6...

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Figure 5: Possible mechanism for the formation of the two atropoisomeric pseudo[2]rotaxanes 2⁺ [Graphic 2] 1^cone and 2⁺1^1,...

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Figure 6: ¹H NMR spectra (600 MHz, CDCl₃, 298 K) of, from bottom to top: hexahexyloxycalix[6]arene 1; a 1:1 m...

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Figure 7: DFT-optimized structures of the: (left) 2⁺ [Graphic 2] 1^cone and (right) 2⁺1^1,2,3-alt pseudorotaxane atropoisome...

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Figure 8: The two pseudorotaxane atropoisomers obtained by threading hexahexyloxycalix[6]arene 1 with monosto...

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Figure 9: The two pseudorotaxane atropoisomers obtained by threading penta-O-methyl-p-tert-butylcalix[5]arene ...

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Figure 10: ¹H NMR spectra (600 MHz, CDCl₃, 298 K) of, from bottom to top: hexahexyloxycalix[6]arene 1; a 1:1 m...

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Full Research Paper

Published 14 Aug 2018

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