A BPTTF-based self-assembled electron-donating triangle capable of C60 binding

Goeb, Sébastien; Bivaud, Sébastien; Dron, Paul I.; Balandier, Jean‐Yves; Chas, Marcos; Sallé, Marc

doi:10.1039/c2cc00065b

Cited by 53 publications

(41 citation statements)

References 48 publications

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“…In particular, the development of systems able to encapsulate and liberate fullerenes has emerged as an attractive method for the purification of this important class of molecules . The development of highly diverse coordination‐based nanoreceptors exhibiting high binding affinity and selectivity for different‐size fullerenes (i.e., trigonal, tetrahedral and cubic cages, barrel, capsule) has been described in the last decade. On the other hand, several strategies have been applied to liberate the sequestered fullerene from supramolecular receptors.…”

Section: Methodsmentioning

confidence: 99%

Reversible C₆₀ Ejection from a Metallocage through the Redox‐Dependent Binding of a Competitive Guest

Colomban

Szalóki

Allain

et al. 2017

Chemistry A European J

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The reversible encapsulation of a tetrapyridyl extended-tetrathiafulvalene (exTTF)-based ligand (m-Py)exTTF by a tetragonal Zn-porphyrin-based prismatic nanocage (1) is described. The reversible uptake and release of the (m-Py)exTTF guest proceeds through drastic electronic and conformational changes occurring upon oxidation of the latter. This reversible system has been explored in a guest-exchange process, by addition of (m-Py)exTTF to the host-guest complex [C ⊂1], leading to fullerene C ejection from the host cavity. Remarkably, the subsequent redox-triggered ejection of (m-Py)exTTF, leads to the recovery of the empty cage 1, which remains available for further C encapsulation. The C ejection is justified by the preferable coordination of the pyridine anchors of (m-Py)exTTF to the two Zn-porphyrin units of 1. This approach, based on the use of a switchable competitive guest, offers a promising new strategy for guest-delivery control.

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Section: Methodsmentioning

confidence: 99%

Reversible C₆₀ Ejection from a Metallocage through the Redox‐Dependent Binding of a Competitive Guest

Colomban

Szalóki

Allain

et al. 2017

Chemistry A European J

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“…Host platforms containing extended p-systems have been designed because of their affinity towards the sphere-like unsaturated structure of fullerenes. In this line, several covalent or supramolecular approaches pursued include: (a) macrocyclic arene-based receptors [18][19][20][21][22][23][24] , (b) macrocyclic structures containing aromatic heterocycles [25][26][27][28] , (c) p-extended TTF receptors [29][30][31][32][33] and (d) macrocyclic or jawlike structures containing porphyrin moieties 17,[34][35][36][37][38][39][40][41][42][43][44][45] . Interestingly, Fujita and co-workers reported the use of the empty channels of a metal-organic framework (MOF) for encapsulating fullerenes upon soaking MOF crystals in fullerene-containing toluene.…”

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confidence: 99%

Sponge-like molecular cage for purification of fullerenes

et al. 2014

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Since fullerenes are available in macroscopic quantities from fullerene soot, large efforts have been geared toward designing efficient strategies to obtain highly pure fullerenes, which can be subsequently applied in multiple research fields. Here we present a supramolecular nanocage synthesized by metal-directed self-assembly, which encapsulates fullerenes of different sizes. Direct experimental evidence is provided for the 1:1 encapsulation of C 60 , C 70 , C 76 , C 78 and C 84 , and solid state structures for the host-guest adducts with C 60 and C 70 have been obtained using X-ray synchrotron radiation. Furthermore, we design a washingbased strategy to exclusively extract pure C 60 from a solid sample of cage charged with a mixture of fullerenes. These results showcase an attractive methodology to selectively extract C 60 from fullerene mixtures, providing a platform to design tuned cages for selective extraction of higher fullerenes. The solid-phase fullerene encapsulation and liberation represent a twist in host-guest chemistry for molecular nanocage structures.

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“…From these formulae, the ratio between the two circumcircle radii can be expressed as [Eq. ]:

true r_{t} / r_{s} = (a / \sqrt 3) / (a / \sqrt 2) = 0.82

…”

Section: Resultsmentioning

confidence: 99%

Visible and Near‐IR Emissions from k²N‐ and k³N‐Terpyridine Rhenium(I) Assemblies Obtained by an [n×1] Head‐to‐Tail Bonding Strategy

Laramée‐Milette

Zaccheroni

Palomba

et al. 2017

Chemistry A European J

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An [n×1] head-to-tail bonding strategy has been used for the synthesis of Re metallacycles. From a k N-dicarbonyl precursor, a single discrete [4×1] square assembly was isolated and characterized, whereas a k N-tricarbonyl precursor led to two major species, a square and a [3×1] triangular assembly. Solid-state X-ray diffraction study has confirmed the high angular distortion (71° to 96°) of the k N precursors. The electrochemical reversibility of the triangular (5) and square (6, 7) assemblies is increased with respect to that of their precursors. Photophysical investigation has confirmed pronounced red-shifts in the emissions of the k N-dicarbonyl species 4 (935 nm) and 7 (980 nm), as confirmed by density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations.

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A BPTTF-based self-assembled electron-donating triangle capable of C60 binding

Cited by 53 publications

References 48 publications

Reversible C₆₀ Ejection from a Metallocage through the Redox‐Dependent Binding of a Competitive Guest

Reversible C₆₀ Ejection from a Metallocage through the Redox‐Dependent Binding of a Competitive Guest

Sponge-like molecular cage for purification of fullerenes

Visible and Near‐IR Emissions from k²N‐ and k³N‐Terpyridine Rhenium(I) Assemblies Obtained by an [n×1] Head‐to‐Tail Bonding Strategy

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A BPTTF-based self-assembled electron-donating triangle capable of C60 binding

Cited by 53 publications

References 48 publications

Reversible C60 Ejection from a Metallocage through the Redox‐Dependent Binding of a Competitive Guest

Reversible C60 Ejection from a Metallocage through the Redox‐Dependent Binding of a Competitive Guest

Sponge-like molecular cage for purification of fullerenes

Visible and Near‐IR Emissions from k2N‐ and k3N‐Terpyridine Rhenium(I) Assemblies Obtained by an [n×1] Head‐to‐Tail Bonding Strategy

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Reversible C₆₀ Ejection from a Metallocage through the Redox‐Dependent Binding of a Competitive Guest

Reversible C₆₀ Ejection from a Metallocage through the Redox‐Dependent Binding of a Competitive Guest

Visible and Near‐IR Emissions from k²N‐ and k³N‐Terpyridine Rhenium(I) Assemblies Obtained by an [n×1] Head‐to‐Tail Bonding Strategy