Doubly Cavitand‐Capped Porphyrin Capsule by Hydrogen Bonds. Issue 8 (20th January 2016)

• Record Type: Journal Article
• Authors: Kishimoto, Kazuki; Nakamura, Munechika; Kobayashi, Kenji
• Is Part Of: Chemistry. Volume 22:Issue 8(2016)
• Page Start: 2629
• Page End: 2633
• Publication Date: 2016-01-20
• Subjects: cavitands -- host–guest systems -- porphyrins -- self-assembly -- supramolecular chemistry; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201504893
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: The components of a 1:2 mixture of meso ‐tetrakis(4‐dodecyl‐3, 5‐dihydroxyphenyl)porphyrin (1 ) and a bowl‐shaped tetrakis(4‐pyridylethynyl)cavitand (2 ) in CDCl3 or C6 D6 self‐assemble quantitatively into the doubly cavitand‐capped porphyrin capsule2⋅1⋅2 through eight ArOH⋅⋅⋅ Npy hydrogen bonds. Capsule2⋅1⋅2 possesses two cavities divided by the porphyrin ring and encapsulates two molecules of 1‐acetoxy‐3, 5‐dimethoxybenzene (G ) as a guest to formG /G @(2⋅1⋅2 ). Remarkable solvent effect was observed, in which the apparent association constant of2⋅1⋅2 withG in C6 D6 was much greater than that in CDCl3 . Abstract : Porphyrin sandwich ! A 1:2 mixture of resorcinol‐porphyrin1 and pyridylethynyl cavitand2 self‐assembles into doubly cavitand‐capped porphyrin capsule2⋅1⋅2 through eight ArOH⋅⋅⋅ Npy hydrogen bonds, which encapsulates two guest molecules (see figure).