Porphyrin nanoparticles as supramolecular systems

Drain, Charles Michael; Smeureanu, Gabriela; Patel, Sandeep; Gong, Xianchang; Garno, Jayne C.; Arijeloye, Julius

doi:10.1039/b607289e

Cited by 80 publications

(94 citation statements)

References 74 publications

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“…Although metastable inorganic colloids [26] and porphyrin nanoparticles [17,27] can be grown with specific shapes under high-energy conditions (vigorous stirring and/or high temperature), until recently reports of molecular crystal growth [15] under such conditions have been scarce, with none progressing beyond the initial molecule-to-nanocrystal stage. As this new frontier in molecular materials emerges, exciting new nanoscale materials will be produced given the near-infinite functional diversity provided by synthetic chemistry; a feature that is not available in the natural environment.…”

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confidence: 99%

Amphiphilic Porphyrin Nanocrystals: Morphology Tuning and Hierarchical Assembly

et al. 2008

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The translation of molecular building blocks into welldefined solid-state structures in a hierarchical fashion (i.e., molecular scale ! nanoscale ! meso-and macroscale) is a key process in many bottom-up materials syntheses. Recent applications of this concept have resulted in new classes of materials that possess well-defined nanometer-sized domains that effect selective catalysis [1] and separation, [2] enable gas storage, [3,4] and facilitate energy transfer.[5] However, assembling such domains into mesoscopic [6,7] or even macroscopic structures remains a major challenge. As the properties of nanomaterials created from small inorganic and organic building blocks can be readily tuned at a molecular level, much interest has been devoted to the assembly of these materials into ever-larger structures. Herein, we demonstrate a hierarchical strategy for producing mesoscopic (and larger) objects from discrete amphiphilic porphyrins. Crystal growth under highly ''energetic'' conditions (i.e., vigorous stirring and heating) was first employed to produce, in a scalable fashion, uniform nanocrystals the morphology of which can be easily modulated by crystal growth conditions as well as the structure of the porphyrin building blocks. These materials were then assembled into macroscopic prisms in the presence of a simple surfactant or selectively partitioned into hydrophobic patterns on glass surfaces. Because the porphyrin nanocrystals formed in the first step have enhanced photostability compared to their molecular constituents, the described hierarchical method for assembling them into larger objects should facilitate practical applications of porphyrin-based materials in transport, [8] imaging, [9] light-harvesting, [10] or catalysis.

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confidence: 99%

Amphiphilic Porphyrin Nanocrystals: Morphology Tuning and Hierarchical Assembly

et al. 2008

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“…The size and structural organization of nanoaggregates of porphyrinoids depends on a variety of factors such as concentration, type of solvent used, temperature and nature of peripheral groups attached to the chromophore. 28 After shaking in phosphate buffered saline (PBS), DLS shows two populations with diameters of 30±4 nm and 284±15 nm, but after sonication for about 15 min, only 82±7 nm particles are observed. The size of the nanoaggregates and strength of intermolecular interactions significantly affects the endocytosis of the photosensitizer by cancer cells, and the propensity of the dyes to disaggregate while adsorbed on the cell membrane or within the cell.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and cell phototoxicity of a triply bridged fused diporphyrin appended with six thioglucose units

Singh

Aggarwal

Bhupathiraju

et al. 2014

Tetrahedron Letters

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“…4 Since the discovery of 'reprecipitation method', a 'bottom up' route to synthesize the organic nanoparticle by Kasai et al 5 different types of innovative results are being reported playing around the process. [6][7][8][9][10][11][12][13][14][15][16][17][18] The central idea of this process is the delicate mixture of good solvent and poor solvent of the target compound. A small volume of milli molar solution of target compound made of relatively volatile solvent is rapidly injected into large amount of vigorously stirred poor solvent of target compound.…”

Section: Introductionmentioning

confidence: 99%

“…On tuning this process for varieties of good solvent and poor solvent pairs along with different parameters, such as temperature, use of microwave and sonication for different π conjugated systems brings several frantic results, which are documented elsewhere. [6][7][8][9][10][11][12][13][14][15][16][17][18] Xianchang Gong et al have claimed that they have first synthesized and characterized the porphyrin nanoparticles using mixing solvent technique. 19 In addition, they have discovered poly ethylene glycol as a stabilizer of the porphyrin nanoparticle.…”

Section: Introductionmentioning

confidence: 99%

Preparation and characterization of free-standing pure porphyrin nanoparticles

Perepogu

Bangal

2008

J Chem Sci

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Preparation and characterization of absolutely pure and stable nanoparticles of 5,10,15,20-meso-tetrakis phenyl porphyrin (TPP) and catalytically repute 5,10,15,20-meso-tetrakis pentaflurophenyl porphyrin (H 2 F 20 TPP) by improved 'reprecipitation method' is described. The innovation of this modified 'reprecipitation method' lies on the judicial selection of organic solvent and amount of porphyrin solution to be injected in the aqueous media. Exactly similar process produces relatively small nanoparticles for TPP than that of H 2 F 20 TPP while the stability of the H 2 F 20 TPP nanoparticles is bit higher than nanoparticles of TPP. Absorption and emission spectra reveal that the formation of nanoparticles for both the cases is induced by J-and H-type aggregation. DFT calculations predict the optimized geometries and frontier molecular orbital, which favours the strength of face-to-face interaction with neighbour molecules to be more facile for TPP than that of H 2 F 20 TPP helping the latter to form bigger and relatively more stable and free-standing nanoparticles. The use of no other compounds except dichloromethane, a highly volatile organic solvent and respective porphyrins give absolutely pure nanoparticles. This improved method will lead to produce organic nanoparticles of π-conjugated systems easily and efficiently.

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Porphyrin nanoparticles as supramolecular systems

Cited by 80 publications

References 74 publications

Amphiphilic Porphyrin Nanocrystals: Morphology Tuning and Hierarchical Assembly

Amphiphilic Porphyrin Nanocrystals: Morphology Tuning and Hierarchical Assembly

Synthesis and cell phototoxicity of a triply bridged fused diporphyrin appended with six thioglucose units

Preparation and characterization of free-standing pure porphyrin nanoparticles

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