Supramolecular Assemblies of Tripodal Porphyrin Hosts and C<sub>60</sub>

Tong, L.; Wietor, Jean‐Luc; Clegg, William; Raithby, Paul R.; Pascu, Sofia I.; Sanders, Jeremy K. M.

doi:10.1002/chem.200701686

Cited by 50 publications

(37 citation statements)

References 70 publications

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“…We will conclude this section dedicated to porphyrin tweezers for fullerenes with the work on tripodal porphyrin receptors reported by the groups of Pascu and Sanders [25]. At first sight, their receptors do not strictly fit in the category of molecular tweezers, since they feature three recognizing motifs each, but as we shall see their binding mode is that of a tweezer.…”

Section: Porphyrin-based Molecular Tweezers For Fullerenesmentioning

confidence: 97%

Molecular tweezers for fullerenes

Pérez

Martín

2010

Pure and Applied Chemistry

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The search for molecular receptors capable of forming stable associates with fullerenes is a very active field of research in fullerene chemistry, with the purification from fullerite and the self-assembly of nanoscale electronic devices as driving forces. The construction of bivalent, tweezer-like receptors featuring two recognizing units connected through a spacer is one of the most successful design strategies employed in this field. Here, we present an overview of the most significant examples of these "molecular tweezers" for fullerenes.

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Section: Porphyrin-based Molecular Tweezers For Fullerenesmentioning

confidence: 97%

Molecular tweezers for fullerenes

Pérez

Martín

2010

Pure and Applied Chemistry

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“…29 Various tripod systems have been synthesized with the goal of fullerene complexation ( Figure 9). 30 One such scaffold involves a tripod with rigid linkers; this system is proposed to make a supramolecular network wherein the net stoichiometry is expected to be 1 : 2 (tripod to fullerene). On the basis of an experimental analysis, it was concluded that each fullerene is always held by two porphyrins.…”

Section: Fullerenesmentioning

confidence: 99%

Porphyrins and Expanded Porphyrins as Receptors

Sessler

Karnas

Sedenberg

2012

Supramolecular Chemistry

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This chapter summarizes recent efforts to use porphyrins and expanded porphyrins as receptors. These unique macrocycles bear resemblance to naturally occurring tetrapyrrolic pigments and have been studied extensively as building blocks for a variety of functional molecular receptors. The introduction discusses the inherent characteristics of porphyrins and their analogs from the perspective of receptor design and is designed to highlight key features. These features include ease of synthesis and functionalization, the hydrogen‐bonding ability of the constituent pyrrolic NH protons, and the fact that the systems in question are often highly colored. This latter feature has afforded an extremely useful means of analyzing host–guest interactions. Because of space limitations, not all of the literature on this topic could be covered in a comprehensive manner. The definition of “receptor” is also limited to species that are thought to be operated via strictly noncovalent‐ or supramolecular‐type interactions. However, this definition is expanded in a few special cases. The goal of this article is not to cite every published article on this topic, but to highlight interesting examples of porphyrin and expanded porphyrins and their utility as receptors. An effort has also been made to describe the analytical techniques used to characterize the resulting host–guest ensembles. This chapter is organized according to the type of guest. One section covers the relatively new area of supramolecular π–π interactions involving porphyrins and nanomaterials, such as fullerenes and nanotubes. Another section discusses porphyrins as receptors for biological entities, including saccharides, peptides, and proteins, as well as DNA. The next section covers porphyrins and expanded porphyrins as anion receptors. This latter treatment includes a discussion of supramolecular electron‐transfer dyads. The use of porphyrins in sensing applications is also presented in summary form. Finally, a perspective on this rapidly growing field of supramolecular chemistry is included in the final remarks. It is hoped that the combination of cited references and listed further readings will allow the interested reader to learn more about this fast‐evolving and fascinating topic.

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“…In a recent example, Sanders and coworkers described the synthesis and fullerene complexation of two different tripodal porphyrin hosts (26-27) by means of X-ray crystallography, and NMR and fluorescence titrations [31]. Surprisingly, the binding of C 60 resulted to be completely different in solution and in the solid state.…”

Section: Receptors For Fullerenes Based On Planar Recognizing Units 73mentioning

confidence: 99%

Supramolecular Receptors for Fullerenes

Fernández

Sánchez

Martán

2010

Ideas in Chemistry and Molecular Sciences

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Since the extraction of fullerenes from the carbon soot using aromatic solvents [1], the interaction between the convex surface of fullerenes and the flat π surface of aromatic moieties has received increasing attention [2]. Fullerene [3] is a polyenic structure constituted by 12 pentagonal and 20 hexagonal rings, in which each carbon atom possess sp 2,3 hybridization [4]. The existence of pentagonal rings provokes a curvature and, therefore, a weak polarization on its surface between the 5 : 6 ring junctions, which represent centers of positive charge, and the negatively charged 6 : 6 fusions [5, 6]. This anisotropic distribution of the electronic charge is the basis to determine the interactions with other substrates.There are two main driving forces to design supramolecular receptors for fullerenes: on one hand, it would be feasible for an effective purification from their natural extraction sources, mainly carbon soot and fullerite. On the other hand, in combination with electron donor receptors, we could design highly organized architectures that can find application in optoelectronics, where the organization of the active materials plays a crucial role in the improvement and precise operation of the devices.In the design of supramolecular receptors for fullerenes we have to consider the neutral features of fullerenes. Therefore, there are some energetic factors to take into account that will determine the final properties and the nature of the interactions involved in the supramolecular complexes: (i) van der Waals forces, (ii) electrostatic interactions, (iii) induction energy, (iv) charge-transfer, and (v) desolvation [7, 8].Considering the nature of all of these noncovalent forces and the geometry and electronic features of C 60 and its higher congeners, van der Waals and solvophobic interactions should be decisive in the stability of the C 60 -receptor complexes [9]. The large global area of fullerenes, consequence of their spherical geometry, and their nonpolar character make these noncovalent effects key factors to attain highly stabilized complexes. Thus, the direct strategy consists in increasing the aromatic

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Supramolecular Assemblies of Tripodal Porphyrin Hosts and C₆₀

Cited by 50 publications

References 70 publications

Molecular tweezers for fullerenes

Molecular tweezers for fullerenes

Porphyrins and Expanded Porphyrins as Receptors

Supramolecular Receptors for Fullerenes

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Supramolecular Assemblies of Tripodal Porphyrin Hosts and C60

Cited by 50 publications

References 70 publications

Molecular tweezers for fullerenes

Molecular tweezers for fullerenes

Porphyrins and Expanded Porphyrins as Receptors

Supramolecular Receptors for Fullerenes

Contact Info

Product

Resources

About

Supramolecular Assemblies of Tripodal Porphyrin Hosts and C₆₀