Fullerene−Porphyrin Constructs

Boyd, Peter D. W.; Reed, Christopher A.

doi:10.1021/ar040168f

Cited by 510 publications

(392 citation statements)

References 57 publications

Supporting

Mentioning

372

Contrasting

Unclassified

Order By: Relevance

“…This has also been called the pentagon-adjacency-penalty rule (PAPR) [4,5]. The focus of studies of classical fullerenes is now moving on to applications [6,7]. However, an increasing number of experimental and theoretical observations indicate that non-classical isomers play an important role in the formation of metallofullerenes and fullerene derivatives [8][9][10].…”

Section: Introductionmentioning

confidence: 99%

From C₅₈to C₆₂and back: Stability, structural similarity, and ring current

Gan

Tian

et al. 2016

J. Comput. Chem.

View full text Add to dashboard Cite

An increasing number of observations show that non-classical isomers may play an important role in the formation of fullerenes and their exo-and endo-derivatives. A quantum-mechanical study of all classical isomers of C 58 , C 60 and C 62 , and all non-classical isomers with at most one square or heptagonal face, was carried out. Calculations at the B3LYP/6-31G* level show that the favoured isomers of C 58 , C 60 and C 62 have closely related structures and suggest plausible inter-conversion and growth pathways amongst low-energy isomers. Similarity of the favoured structures is reinforced by comparison of calculated ring currents induced on faces of these polyhedral cages by radial external magnetic fields, implying patterns of magnetic response similar to those of the stable, isolated-pentagon C 60 molecule.

show abstract

Section: Introductionmentioning

confidence: 99%

From C₅₈to C₆₂and back: Stability, structural similarity, and ring current

Gan

Tian

et al. 2016

J. Comput. Chem.

View full text Add to dashboard Cite

show abstract

“…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.…”

mentioning

confidence: 99%

Sponge-like molecular cage for purification of fullerenes

et al. 2014

View full text Add to dashboard Cite

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.

show abstract

“…[1][2][3][4][5][6][7][8][9][10][11] To achieve these objectives, the formation of stable associates with fullerenes is a prerequisite. In this regard, the group of Kawase has recently coined the term ''concave-convex interactions'' [5][6][7][8] to denote the increase in non-covalent interactions between curved aromatic hosts and guests, and suggested these might play a distinct role in the stabilization of the complexes.…”

mentioning

confidence: 99%

Weighting non-covalent forces in the molecular recognition of C60. Relevance of concave–convex complementarity

et al. 2008

View full text Add to dashboard Cite

The relative contributions of several weak intermolecular forces to the overall stability of the complexes formed between structurally related receptors and [60]fullerene are compared, revealing a discernible contribution from concave-convex complementarity.The construction of molecular receptors for fullerenes continues to be a very active area of research, with their purification from fullerite and the construction of self-organized electroactive nanostructures as main driving forces.1-11 To achieve these objectives, the formation of stable associates with fullerenes is a prerequisite. In this regard, the group of Kawase has recently coined the term ''concave-convex interactions '' 5-8 to denote the increase in non-covalent interactions between curved aromatic hosts and guests, and suggested these might play a distinct role in the stabilization of the complexes. A fair and quantitative comparison of the stability of the complexes formed between fullerenes and receptors based on flat or concave recognizing fragments would require a collection of receptors with enough structural similarity-that is, dissimilar only with regard to the recognizing units-to be studied under experimentally identical conditions. Herein, we investigate the relative contributions of p-p, van der Waals, electrostatic, and concave-convex interactions to the molecular recognition of C 60 by a series of related receptors.We have reported receptors that exploit the concave, electron-rich, aromatic surface of p-extended tetrathiafulvalene derivatives to associate [60]fullerene.9,10 Receptor 1 features 2-[9-(1,3-dithiol-2-ylidene)anthracen-10(9H)-ylidene]-1,3-dithiole (exTTF) as the recognizing element (Chart 1).9 Despite the lack of preorganization in its design, 1 forms stable associates with C 60 (see Table 1). Since a charge-transfer band is experimentally observed in the UV-Vis titrations (l max E 482 nm) of 1 against C 60 , up to four ''separate'' contributions to the stability of the complex can be envisaged: p-p aromatic interactions, van der Waals forces, electrostatic interactions, and concave-convex complementarity. With the aim of weighting those contributions separately, we designed and synthesized a collection of tweezer-like receptors, 1-4, in which the size, shape and electronic character of the recognizing motifs are selectively tuned. The solubility of receptors 1-4 at the concentrations employed in titration experiments (r1 mM) is sufficient to rule out solvophobic effects as a major factor in the stability of the complexes.As shown in Chart 1, receptors 1-4 consist of an isophthalic diester spacer to which two units of the corresponding recognizing moieties are attached. All the receptors were synthesized from the commercially available or previously reported methylene alcohols and isophthaloyl dichloride by standard condensation reactions in good to excellent yields, and unambiguously characterized.w Table 1 and are the average of at least two titration experiments (for details, see the Supplementary Informationw). Unfo...

show abstract

Fullerene−Porphyrin Constructs

Cited by 510 publications

References 57 publications

From C₅₈to C₆₂and back: Stability, structural similarity, and ring current

From C₅₈to C₆₂and back: Stability, structural similarity, and ring current

Sponge-like molecular cage for purification of fullerenes

Weighting non-covalent forces in the molecular recognition of C60. Relevance of concave–convex complementarity

Contact Info

Product

Resources

About

Fullerene−Porphyrin Constructs

Cited by 510 publications

References 57 publications

From C58to C62and back: Stability, structural similarity, and ring current

From C58to C62and back: Stability, structural similarity, and ring current

Sponge-like molecular cage for purification of fullerenes

Weighting non-covalent forces in the molecular recognition of C60. Relevance of concave–convex complementarity

Contact Info

Product

Resources

About

From C₅₈to C₆₂and back: Stability, structural similarity, and ring current

From C₅₈to C₆₂and back: Stability, structural similarity, and ring current