Double Porphyrin Cage Compounds

Stout, Kathleen; Peters, Theo P. J.; Mabesoone, Mathijs F. J.; Visschers, Fabian L L; Meijer, Eline M; Klop, Joëlle-Rose; Berg, Jeroen van den; White, Paul B.; Rowan, Alan E.; Nolte, Roeland J. M.; Elemans, Johannes A. A. W.

doi:10.1002/ejoc.202001211

Cited by 3 publications

References 55 publications

(104 reference statements)

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Doubly Cavitand‐Capped Zn‐Porphyrin Capsule with Simultaneous Encapsulation of Guest and Ligand, and Its Application to Doubly Cavitand‐Capped Double‐Decker Zn‐Porphyrin Capsule

2021

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A 1 : 2 mixture of Zn-meso-tetrakis(4-dodecyl-3,5dihydroxyphenyl)porphyrin (1-Zn) and tetrakis(4pyridylethynyl)cavitand (2) in C 6 D 6 self-assembles quantitatively into the doubly cavitand-capped Zn-porphyrin capsule 2 • 1-Zn • 2 with two cavities divided by the porphyrin ring via eight ArOH•••Npy hydrogen bonds. Simultaneous encapsulation of 1-acetoxy-3,5-dimethoxybenzene (G) and 4-(4-methylphenyl)pyridine (L2) in 2 • 1-Zn • 2 preferentially occurs to form G/L2@(2 • 1-Zn • 2). A 1 : 1 mixture of 1-Zn and 2 in the presence of G and L2 self-assembles into the G-encapsulating half-capsule G@(2 • 1-Zn) • L2 with coordination of L2 at the outer side of 2 • 1-Zn. A 2 : 2 : 1 mixture of 1-Zn, 2, and 1,4diazabicyclo[2.2.2]octane (L3) in the presence of G selfassembles preferentially into the G-encapsulating doubly cavitand-capped double-decker Zn-porphyrin capsule G/G@-(2 • 1-Zn • L3 • 1-Zn • 2) with coordination of L3 between two hydrogen-bonded 1-Zn subunits. Thus, selective formation of these cavitand-porphyrin capsules can be controlled by the stoichiometry of 1-Zn and 2 as well as the character of Nligands.

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Doubly Cavitand‐Capped Zn‐Porphyrin Capsule with Simultaneous Encapsulation of Guest and Ligand, and Its Application to Doubly Cavitand‐Capped Double‐Decker Zn‐Porphyrin Capsule

2021

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A Highly Sterically Congested Bis‐Zinc‐Porphyrin Containing a Single Buta‐1,3‐diyne Linkage: From a Serendipitous Finding to Supramolecular Encapsulation

et al. 2023

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A unique example of a bis‐zinc‐porphyrin chemical system in which both macrocycles are covalently connected with a single, short buta‐1,3‐diyne linkage placed at the ortho sites of the meso phenyl rings is presented. This dimeric compound resulted from an homo‐coupling side‐reaction taking place during a copper‐catalyzed click reaction between an alkyne porphyrin and 2‐azidopyridine derivatives. Its unexpected formation was rationalized by control experiments and an improved synthesis was achieved under copper‐catalyzed Glaser‐Hay coupling reaction conditions. This highly sterically congested bis‐zinc‐porphyrin derivative behaved as a supramolecular host for encapsulating ditopic molecular guests such as 1,4‐diazabicyclo[2.2.2]octane (DABCO) with association constant K1.1 in the order of 106 M−1. This value is comparable to current systems that typically feature several connecting linkages between the two zinc‐porphyrin sites resulting in (supra)molecular cages ensuring a high pre‐organization. As such, the requirements to take benefit from supramolecular encapsulation can be reduced to a highly rigid, minimal covalent linkage of four atoms between zinc‐porphyrins as herein described.

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Eight-membered and larger rings

Moorefield¹,

Newkome

2021

Progress in Heterocyclic Chemistry

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Double Porphyrin Cage Compounds

Cited by 3 publications

References 55 publications

Doubly Cavitand‐Capped Zn‐Porphyrin Capsule with Simultaneous Encapsulation of Guest and Ligand, and Its Application to Doubly Cavitand‐Capped Double‐Decker Zn‐Porphyrin Capsule

Doubly Cavitand‐Capped Zn‐Porphyrin Capsule with Simultaneous Encapsulation of Guest and Ligand, and Its Application to Doubly Cavitand‐Capped Double‐Decker Zn‐Porphyrin Capsule

A Highly Sterically Congested Bis‐Zinc‐Porphyrin Containing a Single Buta‐1,3‐diyne Linkage: From a Serendipitous Finding to Supramolecular Encapsulation

Eight-membered and larger rings

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