Self-Assembly of Oligomeric Porphyrin Rings

Haycock, Richard A.; Hunter, Christopher A.; James, David A.; Michelsen, U.; Sutton, Liam R.

doi:10.1021/ol000129d

Cited by 105 publications

(43 citation statements)

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“…For decades they have been subject to research, mainly owed to their outstanding photophysical properties. The metal binding capability and the redox behaviour of these complexes make porphyrines an essential component of 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 [3,4] or (b) hydrogen bonds or non-covalent interactions between substituents, e.g. in ref [5].…”

Section: Introductionmentioning

confidence: 99%

“…An estimation of the dimer binding energy of (zinc) porphyrine by analysing the thermodynamics of metal complexation vs. stacking interaction gave -11.5 ±2. 4 Energies were then recalculated with the recently introduced double-hybrid density functional B2-PLYP [35], that contains a perturbative (virtual orbital dependent) contribution 5 We also applied the SCS-MP2 model [38], a recently introduced improved version of standard Møller-Plesset perturbation theory in which the correlation energy is partitioned into parallel-and antiparallel-spin components which are separately scaled. It provides significantly improved energetics compared to standard MP2 for a wide variety of chemical systems often reaching QCISD(T) accuracy and also corrects for the systematic overestimation of MP2 for van der Waals interactions in unsaturated systems [38,39,40,41,42].…”

Section: Introductionmentioning

confidence: 99%

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Structure and binding energies of the porphine dimer

Mück‐Lichtenfeld¹

2007

Molecular Physics

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Structure and binding energies of the porphine dimer

Mück‐Lichtenfeld¹

2007

Molecular Physics

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“…4(b)]. 125,126 Simultaneously Kobuke reported the self-assembly of bis((Nmethyl)imidazolyl Zn(II)-porphyrin) ImZnP3 into polymeric supramolecular arrays, driven by the intermolecular Zncoordination of the methylimidazolyl side groups (Fig. 5).…”

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confidence: 96%

Controlling supramolecular polymerization through multicomponent self‐assembly

Besenius

2016

J. Polym. Sci. Part A: Polym. Chem.

122

102

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The self-assembly into supramolecular polymers is a process driven by reversible non-covalent interactions between monomers, and gives access to materials applications incorporating mechanical, biological, optical or electronic functionalities. Compared to the achievements in precision polymer synthesis via living and controlled covalent polymerization processes, supramolecular chemists have only just learned how to developed strategies that allow similar control over polymer length, (co)monomer sequence and morphology (random, alternating or blocked ordering). This highlight article discusses the unique opportunities that arise when coassembling multicomponent supramolecular polymers, and focusses on four strategies in order to control the polymer architecture, size, stability and its stimuli-responsive properties: (1) endcapping of supramolecular polymers, (2) biomimetic templated polymerization, (3) controlled selectivity and reactivity in supramolecular copolymerization, and (4) living supramolecular polymerization. In contrast to the traditional focus on equilibrium systems, our emphasis is also on the manipulation of selfassembly kinetics of synthetic supramolecular systems. V C 2016

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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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Self-Assembly of Oligomeric Porphyrin Rings

Abstract: A cobalt porphyrin equipped with two different but geometrically complementary pyridine ligands self-assembles to form an unusually stable complex with approximately 12 porphyrin monomers arranged in a macrocyclic array.

Cited by 105 publications

References 6 publications

Structure and binding energies of the porphine dimer

Structure and binding energies of the porphine dimer

Controlling supramolecular polymerization through multicomponent self‐assembly

Supramolecular polymer formed by reversible self-assembly of tetrakisporphyrin

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