Noncovalent Assembly of [2]Rotaxane Architectures

Hunter, Christopher A.; Low, Caroline M. R.; Packer, Martin J.; Spey, Sharon E.; Vinter, Jeremy G.; Vysotsky, Myroslav O.; Zonta, Cristiano

doi:10.1002/1521-3773(20010716)40:14<2678::aid-anie2678>3.0.co;2-u

Cited by 99 publications

(40 citation statements)

References 45 publications

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“…information [92]. Later, inspired by the work of Williamson, we started to develop a program for the calculation of the structures of supramolecular complexes using CIS values and NOEs [130,131]. The program generates a large number of conformations, and for each of them, the CIS values are calculated and compared with the experimental values.…”

Section: Continuous Refinement With Chemical Shiftsmentioning

confidence: 99%

From structure to chemical shift and vice-versa

Hunter

Packer

Zonta

2005

Progress in Nuclear Magnetic Resonance Spectroscopy

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Section: Continuous Refinement With Chemical Shiftsmentioning

confidence: 99%

From structure to chemical shift and vice-versa

Hunter

Packer

Zonta

2005

Progress in Nuclear Magnetic Resonance Spectroscopy

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“…Hunter and coworkers developed unique self-assembled porphyrin arrays (14)(15)(16)(17)(18). Giant porphyrin arrays and large porphyrin wheels via metal coordination for modeling light-harvesting antenna have been reported by .…”

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confidence: 99%

Supramolecular polymer formed by reversible self-assembly of tetrakisporphyrin

Haino

Fujii

Watanabe

et al. 2009

Proc. Natl. Acad. Sci. U.S.A.

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S-shaped tetrakisporphyrin 2 forms supramolecular polymeric assemblies via a complementary affinity of its bisporphyrin units in solution. The self-association constant determined by applying the isodesmic model is >10 6 L mol ؊1 , which suggests that a sizable polymer forms at millimolar concentrations at room temperature. The electron deficient aromatic guest (TNF) binds within the molecular clefts provided by the bisporphyrin units via a chargetransfer interaction. This guest complexation completely disrupts supramolecular polymeric assembly. The long, fibrous fragments of the polymeric assemblies were characterized by atomic-force microscopy imaging of a film cast on a mica surface. The polymeric assemblies have lengths of >1m and show a coiled structure with a higher level of organization. The approach discussed in this report concerning the quick preparation of supramolecular polymeric assemblies driven by noncovalent forces sets the stage for the preparation of a previously undescribed class of macromolecular porphyrin architectures.porphyrin ͉ supramolecular chemistry S ignificant effort has been directed toward elucidating the energy transport phenomena occurring in natural lightharvesting complexes. A variety of porphyrin-based model compounds have been created to mimic natural light-harvesting complexes with the goal of applying them to artificial lightharvesting systems and molecular photonic devices (1-4). Among them, nanometric multiporphyrin arrays are the most challenging target, wherein, their covalent synthesis offers a high stability and a precisely controlled arrangement of multiporphyrin arrays (5, 6). Unfortunately, the growth of size and complexity of these systems makes their synthesis tedious and inefficient.In contrast, supramolecular self-assembly is a versatile alternative and offers the quick construction of 1-, 2-, or 3-dimensional nanometric architectures that have discrete structures, properties, and functions in which the molecular components are held together by reversible interactions (7-11). Self-assembled nanometric multiporphyrin arrays having well-defined shapes and dimensions provide unique optical and electrochemical properties for photochemical energy conversion and storage. As a consequence, their practical applications can be foreseen in the field of molecular electronics: conductive molecular wires, switches, and photovoltaic cells. These creative developments should pave the way for research directions in creating key materials for emerging field of nanotechnology and science.Coordination-driven self-assembly of porphyrin is one of the most useful approaches for developing large and elaborate molecular architectures (12, 13). Hunter and coworkers developed unique self-assembled porphyrin arrays (14-18). Giant porphyrin arrays and large porphyrin wheels via metal coordination for modeling light-harvesting antenna have been reported by . Aida and coworkers have investigated self-assembled nanometric porphyrin arrays (27-29). There are limited examples of porphyrin self...

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“…Due to the similarity of our system with those reported [6,7] and since the efficient constructions of [2]rotaxanes require a high affinity between the wheel and the axle molecules, we decided to use axle molecules containing an adipamide unit. When macrocycle 2 (4mM) and four equivalents of the adipamide axle 3 were mixed in CDCl 3 at room temperature the 1 H-NMR spectrum immediately showed a slight downfield shift of the NH resonances of the selfassembled macrocycle 2, indicating the formation of an hydrogen bonded-complex even in the presence of competing triflate anions.…”

Section: Resultsmentioning

confidence: 99%

“…Among possible weak reversible bonds, the metal-ligand interaction or coordinate bond is very suitable for this purpose because both strength and geometry are tunable with the selection of the right combination of metal and ligand. Based on these ideas, rotaxanes in which coordinate bonds are used for attaching stoppers to the linear molecule [5] or for the construction of the macrocycle unit [6,7] have been recently reported. The macrocycles used in these two later examples contain reversible coordination bonds N-Os(VI) [6] and N-Zn(II) [7], and in both cases the metal lacks of non-coordinate metal counter ions.…”

Section: Introductionmentioning

confidence: 99%

“…Based on these ideas, rotaxanes in which coordinate bonds are used for attaching stoppers to the linear molecule [5] or for the construction of the macrocycle unit [6,7] have been recently reported. The macrocycles used in these two later examples contain reversible coordination bonds N-Os(VI) [6] and N-Zn(II) [7], and in both cases the metal lacks of non-coordinate metal counter ions. Here we describe an example of non-covalent self-assembly of a [2]rotaxane like complex with a macrocycle containing reversible coordinate N-Pt(II) bonds and featuring non coordinate metal counter ions (triflate) which may compete with the template threading process based on the formation of intermolecular hydrogen bonds.…”

Section: Introductionmentioning

confidence: 99%

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