Multiporphyrinic Cages: Architectures and Functions

Durot, Stéphanie; Taesch, Julien; Heitz, Valérie

doi:10.1021/cr400673y

Cited by 265 publications

(186 citation statements)

References 301 publications

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“…We believe that the general approach presented here is applicable to the synthesis of ultra-large,s hapepersistent organic cages leading to highly porous molecular solids.B esides the porosity,t he shape-persistent cages built with porphyrin units may exhibit interesting chemical, photophysical, electrochemical, and biological properties. [20] Furthermore,the large organic cages may encapsulate intriguing guests such as fullerenes in the hydrophobic cavity through host-guest interactions. [21] Finally,o nce metalated, the porphyrin boxes can be utilized as ab uilding block to generate metal-organic frameworks (MOFs) with many exciting application perspectives.W ork along these lines is in progress.…”

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confidence: 99%

Porphyrin Boxes: Rationally Designed Porous Organic Cages

et al. 2015

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The porphyrin boxes (PB-1 and PB-2), which are rationally designed porous organic cages with a large cavity using well-defined and rigid 3-connected triangular and 4-connected square shaped building units are reported. PB-1 has a cavity as large as 1.95 nm in diameter and shows high chemical stability in a broad pH range (4.8 to 13) in aqueous media. The crystalline nature as well as cavity structure of the shape-persistent organic cage crystals were intact even after complete removal of guest molecules, leading to one of the highest surface areas (1370 m(2) g(-1)) among the known porous organic molecular solids. The size of the cavities and windows of the porous organic cages can be modulated using different sized building units while maintaining the topology of the cages, as illustrated with PB-2. Interestingly, PB-2 crystals showed unusual N2 sorption isotherms as well as high selectivity for CO2 over N2 and CH4 (201 and 47.9, respectively at 273 K at 1 bar).

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Porphyrin Boxes: Rationally Designed Porous Organic Cages

et al. 2015

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“…[11] Self-assembled porphyrin capsules or cages have been intensively studied. [12] However, in almost all cases, porphyrin subunits have been used as exteriorw alls of self-assembled capsules. Although af ew examples of singly macrocyclic host-capped self-assembled porphyrinc apsules have been reported, [13][14][15] ad oublym acrocyclic host-capped self-assembled porphyrin capsulei su nprecedented, [16,17] probably because of al ack of an appropriate moleculard esign.T he merits of ad oubly macrocyclic host-capped porphyrin capsulea re that two same guest molecules,s uch as electron donor or acceptor,o rt wo different guest molecules, such as ac ombinationo fs ubstrate and ligand or electrond onor and acceptor,c an be encapsulated simultaneously and such guest encapsulation would endow this type of porphyrin capsulew ith potential as af unctional material.…”

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Doubly Cavitand‐Capped Porphyrin Capsule by Hydrogen Bonds

Kishimoto

Nakamura

Kobayashi

2016

Chemistry A European J

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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 capsule 2⋅1⋅2 through eight ArOH⋅⋅⋅Npy hydrogen bonds. Capsule 2⋅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 form G/G@(2⋅1⋅2). Remarkable solvent effect was observed, in which the apparent association constant of 2⋅1⋅2 with G in C6 D6 was much greater than that in CDCl3.

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“…54 The last work reviewed in this section includes both types. The design and function of smaller porphyrinic cage architectures have been recently reviewed by Durot et al 55 Kanaizuka et al created a one-dimensional coordination porphyrin polymer grown off glass substrates (Fig. 20).…”

Section: Coordination Polymersmentioning

confidence: 99%

Porphyrin polymers and organic frameworks

Day

Wamser

Walter

2015

Polymer International

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The versatility of porphyrins as optoelectronic or catalytic units makes them attractive elements for inclusion in functional materials. Polymers that include porphyrins have been created with a wide variety of structures and used in a wide range of applications. This review covers recent developments in the synthesis, characterization and applications of polymeric materials in which porphyrins are key components of the repeat units, including the rapidly growing area of metal-organic frameworks and related covalent organic frameworks. © 2015 Society of Chemical Industry Keywords: review; porphyrin; metal-organic framework; covalent organic framework PORPHYRINS AS FUNCTIONAL BUILDING BLOCKSThe porphyrin ring and its many structural relatives are common functional units in both natural and synthetic systems (Fig. 1). Porphyrins have a variety of properties that allow them to be useful in applications, especially their broad-ranging optoelectronic and catalytic capabilities. Furthermore, these properties are readily modulated by incorporation of various metals inside the ring or by substituent effects at various locations around the ring. In many cases, nature provides guidance for specific structure-function correlations and applications -the so-called biomimetic approaches. In nature, porphyrin (heme) units are typically embedded in a biological matrix that controls the environment of and access to the porphyrin. In synthetic systems, porphyrins in polymeric matrices have been developed in similar fashion to help control the specific application.In this review, we briefly cite previous reviews and summarize recent results regarding the synthesis, structure, properties and applications of polymeric porphyrins. We only include polymers that contain multiple porphyrin units as an integral part of the polymer, as opposed to polymeric matrices that are simply used to encapsulate individual porphyrin units. We also cover the rapidly growing field of metal-organic frameworks (MOFs) and covalent organic frameworks (COFs), where they specifically include porphyrins as a key component of the framework. Structures related to porphyrins (phthalocyanines, corroles, chlorins, etc.) and porphyrin dimers are not covered, but some porphyrin oligomers are discussed; reviews on many of these are available in the comprehensive series Handbook of Porphyrin Science.

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Multiporphyrinic Cages: Architectures and Functions

Cited by 265 publications

References 301 publications

Porphyrin Boxes: Rationally Designed Porous Organic Cages

Porphyrin Boxes: Rationally Designed Porous Organic Cages

Doubly Cavitand‐Capped Porphyrin Capsule by Hydrogen Bonds

Porphyrin polymers and organic frameworks

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