Self-assembled multiporphyrin arrays mediated by self-complementary quadruple hydrogen bond motifs

Drain, Charles Michael; Shi, Xinxu; Milic, Tatjana; Nifiatis, Fotis

doi:10.1039/b008045o

Cited by 51 publications

(40 citation statements)

References 17 publications

(10 reference statements)

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“…69,70,89,120 The right angle disposition of 5,15-(3,5-diacetamido-4-pyridyl) groups results in self-complementary interactions between porphyrins to form a square structure in solution, but in crystals of this array one of the porphyrins cants at an angle to form a square helical structure that allows denser packing 89,120. This illustrates the differences that can be found between solution and solid state structures.…”

Section: Self-organization By Hydrogen Bondsmentioning

confidence: 97%

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: 97%

Self-Organized Porphyrinic Materials

2009

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“…A variety of nanofibers have also been reported [61–64]. Coordination chemistry is most often used because the metal ion binding geometry can be exploited as a design element and coordination bonds are robust [65], but electrostatic [26, 54] and hydrogen bond [52, 66] interactions are also used in formation of porphyrinic materials. Reversible coordination of metal ions dictates the conformation of porphyrins linked to the 5,5’ positions of a 2,2’-bipyridyl bridge thereby reversibly switching the electronic communication between the chromophores [67].…”

Section: Introductionmentioning

confidence: 99%

Porphyrins as molecular electronic components of functional devices

Jurow¹,

Schuckman²,

Batteas³

et al. 2010

Coordination Chemistry Reviews

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The proposal that molecules can perform electronic functions in devices such as diodes, rectifiers, wires, capacitors, or serve as functional materials for electronic or magnetic memory, has stimulated intense research across physics, chemistry, and engineering for over 35 years. Because biology uses porphyrins and metalloporphyrins as catalysts, small molecule transporters, electrical conduits, and energy transducers in photosynthesis, porphyrins are an obvious class of molecules to investigate for molecular electronic functions. Of the numerous kinds of molecules under investigation for molecular electronics applications, porphyrins and their related macrocycles are of particular interest because they are robust and their electronic properties can be tuned by chelation of a metal ion and substitution on the macrocycle. The other porphyrinoids have equally variable and adjustable photophysical properties, thus photonic applications are potentiated. At least in the near term, realistic architectures for molecular electronics will require self-organization or nanoprinting on surfaces. This review concentrates on self-organized porphyrinoids as components of working electronic devices on electronically active substrates with particular emphasis on the effect of surface, molecular design, molecular orientation and matrix on the detailed electronic properties of single molecules.

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“…Porphyrinoids appended with H-bond motifs can assemble into diverse arrangements such as rosettes, squares, tapes, and nanoparticles for materials for solar energy harvesting, photonic devices, sensors, catalysts, and understanding biological electron transport. 4–6 In addition to directing supramolecular architectures, the functional groups on the macrocycle and mode of assembly can modulate photophysical and chemical properties of chromophoric arrays. Responsive H-bond materials, whereby the supramolecular structure can be modulated by environmental conditions such as temperature or solvent, can find applications as catalytic hosts for specific guests, or control of electronic communication between subunits.…”

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confidence: 99%

“…7 While functional materials of porphyrins self-assembled by hydrogen bonding have demonstrated utility, 5 porphyrins bearing hydrogen bonding motifs rigidly attached can be difficult to synthesize. 4 …”

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“…Two notable features are: the porphyrins are made in one step, and the supramolecular dynamics are significantly reduced because all four meso positions participate in the assembly instead of two. 4–6 The free base and zinc complexes of two different macrocycles are used to form the cages (Scheme 2), where interconversion of the atropisomers of the uracylporphyrins is required. NMR, light scattering, and photophysical properties in solution indicate formation of the cages, and atomic force microscopy (AFM) elucidates the self-organization of the materials cast onto mica.…”

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