Synthesis and molecular recognition properties of a self-assembling molecule consisted of a porphyrin core and two hydrogen-bonding moieties

Fujimoto, Kazuhisa; Toyoshi, Tetsuya; Doi, Yasuhiro; Inoûye, Masahiko

doi:10.1016/j.msec.2006.04.002

Cited by 9 publications

(10 citation statements)

References 16 publications

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“…Porphyrins bearing multiple H-bonding donor and acceptor groups are being investigated as components of new materials for a diverse array of applications,87 and to study the fundamental photophysics of these systems 88. Because the porphyrin macrocycle is rigid, the placement of rigid H-bonding moieties and their relative orientation allows the design of a variety of specific architectures.…”

Section: Self-organization By Hydrogen Bondsmentioning

confidence: 99%

Self-Organized Porphyrinic Materials

2009

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The self-assembly and self-organization of porphyrins and related macrocycles enables the bottomup fabrication of photonic materials for fundamental studies of the photophysics of these materials and for diverse applications. This rapidly developing field encompasses a broad range of disciplines including molecular design and synthesis, materials formation and characterization, and the design and evaluation of devices. Since the self-assembly of porphyrins by electrostatic interactions in the late 1980s to the present, there has been an ever increasing degree of sophistication in the design of porphyrins that self-assemble into discrete arrays or self-organize into polymeric systems. These strategies exploit ionic interactions, hydrogen bonding, coordination chemistry, and dispersion forces to form supramolecular systems with varying degrees of hierarchical order. This review concentrates on the methods to form supramolecular porphyrinic systems by intermolecular interactions other than coordination chemistry, the characterization and properties of these photonic materials, and the prospects for using these in devices. The review is heuristically organized by the predominant intermolecular interactions used and emphasizes how the organization affects properties and potential performance in devices.

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Section: Self-organization By Hydrogen Bondsmentioning

confidence: 99%

Self-Organized Porphyrinic Materials

2009

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“…Both types have attracted substantial attention thanks to their host–guest and stimuli‐responsive behaviour [9, 10] . The two methods of assembly were utilised together to prepare cage‐like molecules [11–17] . However, these examples are not truly hybrid container molecules, since one of the self‐assembly components is not incorporated directly in the topology, and therefore removal of any assembling part (hydrogen‐bonding or metal‐coordination) does not result in the change of the complex topology.…”

Section: Figurementioning

confidence: 99%

“…[9,10] The two methods of assembly were utilised together to preparec agelike molecules. [11][12][13][14][15][16][17] However,t hese examples are not truly hybrid container molecules, since one of the self-assembly components is not incorporated directly in the topology,a nd therefore removal of any assembling part (hydrogen-bonding or metal-coordination) does not result in the change of the complex topology.O nt he other hand,w ell-defined discrete containers with genuine hybrid character are rare. [18][19][20][21] The recently described hybrid cage from Shi et al is the beste xample.…”

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confidence: 99%

Stimuli‐Responsive Self‐Sorting Hybrid Hydrogen‐Bonded/Metal‐Coordinated Cage

Motloch

Hunter

2021

Chemistry A European J

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The self‐assembly of a unique molecular container is reported: a hybrid hydrogen‐bonded/metal‐coordinated cage where both hydrogen‐bonding and metal‐coordination form the crucial part of the topology. The hybrid cage was prepared combining hydrogen‐bonded rosette motif and palladium(II)/platinum(II) coordination to a pyridine ligand. It was also shown that the hybrid cage could be prepared by integrative self‐sorting from simple components. For the first time the genuine dual character of the hybrid cage was manifested as both self‐assembling parts responded selectively to different stimuli (such as phosphine and cyanurate), which resulted in the disassembly of the cage.

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“…Derivatives of 2-amino-3H-pyrimidin-4-one or isocytosine have shown significant anticancer [39], antimicrobial [40] and pharmacological properties [41]. Their behavior in nucleobase recognition processes [42] and as self-assembling hydrogen-bonding modules in macromolecular systems have also been studied [43].…”

Section: Introductionmentioning

confidence: 99%