Self-assembled porphyrin microrods and observation of structure-induced iridescence

Martelli, Cícero; Canning, John; Khoury, Tony; Skivesen, N.; Kristensen, Martin; Huyang, George; Jensen, Paul R.; Neto, Chiara; Sum, Tze Jing; Hovgaard, Mads Bruun; Gibson, Brant C.; Crossley, Maxwell J.

doi:10.1039/b917695k

Cited by 9 publications

(9 citation statements)

References 31 publications

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“…These functionalized porphyrins have been used as promising photosensitizers in dye‐sensitized solar cells . In addition, peripheral substituents play important roles during the construction of porphyrin‐based molecular materials through further substituent transformations or coordination‐driven self‐assembly . For these purposes, a considerable number of synthetic methods for the introduction of a variety of substituents have been developed over several decades.…”

Section: Introductionmentioning

confidence: 99%

Versatile and Catalyst‐Free Methods for the Introduction of Group‐16 Elements at the meso‐Positions of Diarylporphyrins

et al. 2018

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This report describes versatile and catalyst-free methods for the introduction of group-16 elements at the meso-positions of diarylporphyrins. The methods involve nucleophilic aromatic substitution (S N Ar) of the meso-bromodiarylporphyrin. The reaction proceeds in almost quantitative yield in most cases. Reactions with various phenols afford the corresponding meso-phenoxyporphyrins, except for the reaction with 4-hydroxypyridine, which affords a meso-(N-pyridonyl)porphyrin. With the exception of thiocyanate, reac-tions involving sulfur-centered nucleophiles proceed smoothly and afford the corresponding functionalized porphyrins, including a meso-sulfonylporphyrin that was obtained from benzenesulfinate. To overcome problems associated with the handling of chalcogenols (instability, bad odors), we also used dichalcogenides as nucleophile precursors to afford the corresponding meso-sulfanyl or selanylporphyrins. The instability of a novel meso-tellanylporphyrin is also revealed.[a] Dr.

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Section: Introductionmentioning

confidence: 99%

Versatile and Catalyst‐Free Methods for the Introduction of Group‐16 Elements at the meso‐Positions of Diarylporphyrins

et al. 2018

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“…Recently, photonic wires made from self-assembled porphyrin structures were demonstrated on both quartz and silicon [2][3][4]. Those produced on silica have so far been of greater uniformity and higher optical transparency, displaying iridescence associated with structural layers within the wires.…”

Section: Self-assembled Porphyrin Wires and Slabsmentioning

confidence: 99%

“…The next generation of technologies spanning both electronics and photonics are self-assembled supramolecular structures including wires and films [1][2][3][4]. Of these supramolecular structures, porphyrin-based assemblies are particularly attractive in photonics, having a number of advantages which include unmatched chemical structure engineering [4] for specific functionality ranging from non-linear optics [5][6][7] (high Kerr coefficients) to potentially novel sensing and filter elements and optical limiting devices using heavy metals [8]. Other active systems can be readily incorporated or attached to the various end groups.…”

Section: Introductionmentioning

confidence: 99%

“…The exploitation of certain properties of organic molecular systems for optoelectronic functionality in waveguide technology, generally, is of current topical interest [9]. Recently, the self-assembly of supramolecular structures such as porphyrins into 1D and 2D structures potentially useful for waveguide technologies has been demonstrated [2][3][4]. More broadly, self-assembly already plays a key role in other areas including DNA colloidal self-assembly for diagnostics [10] and the general preparation of various thin films layer by layer for bulk optoelectronic applications [1].…”

Section: Introductionmentioning

confidence: 99%

“…While the entire self-assembly of an integrated circuit is currently challenging today's technology, the recent demonstration of self-assembled porphyrin wires and slabs [2][3][4] suggests that supramolecular self-assembly can be integrated to existing major photonic platform technologies, overcoming key limitations in niche areas of these expanding platforms.…”

Section: Introductionmentioning

confidence: 99%

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Focused ion beam processing and engineering of devices in self-assembled supramolecular structures

Huyang¹,

Canning²,

Gibson³

et al. 2009

Nanotechnology

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Self-assembled supramolecular structures such as optical wires, films and 2D slabs offer a new generation of electronic and optical devices. In particular, self-assembled porphyrin devices, including those integrated onto silica and silicon platforms, open new opportunities in photonic applications spanning molecular biosensing, photovoltaics and telecommunications. All reports to date, however, largely highlight the potential but have not established a clear pathway to the actual implementation of more complex device prototypes. In this paper, we propose and demonstrate the use of a focused ion beam (FIB) to process and fabricate devices in porphyrin-based supramolecular structures. These self-assembled structures have an initial root mean squared (rms) values for surface roughness of < 0.5 nm as measured by atomic force microscopy. Under appropriate FIB processing and cutting conditions, the rms value for surface roughness falls to < 0.4 nm, comparable with some of the best optical flatnesses obtained within, for example, structured optical fibres and integrated optical waveguides. The milling rate of the porphyrin structures was estimated to be approximately 70% of that of silica. The versatility of a FIB as a tool for rapid processing and fabricating 1D and 2D photonic waveguide structures within supramolecular self-assembled platforms is demonstrated by fabricating a 2D coupler, setting the groundwork for true optical device engineering and integration using these new organic systems.

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Synthesis of Steroid–Porphyrin Conjugates from Oestradiol, Oestrone, and Lithocholic Acid*

et al. 2014

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The synthesis of porphyrin–steroid conjugates is examined using the natural steroids oestradiol, oestrone, and lithocholic acid as precursors. Two strategies differing in the timing of formation of the steroid–porphyrin linkage leading to four different construction motifs are explored. Two approaches are based on a strategy of introduction of steroidal components in the porphyrin-forming reaction involving condensation of steroidal-alkylaldehydes and pyrrole to give 5,10,15,20-tetrakis(steroidal-alkyl)porphyrins and differ in the way in which the required aldehyde is introduced to the steroidal component. In the other strategy, a steroidal component is introduced by post-porphyrin synthesis reactions and here also two approaches were explored, one involving nucleophilic substitution and the other esterification. Of the four approaches investigated, the most efficient and most versatile one attaches the steroidal components late in the sequence to a 5,10,15,20-tetra(ω-haloalkyl)porphyrin by a nucleophilic substitution reaction. In this way, a 5,10,15,20-tetrakis[oestrone-linked-heptyl)porphyrin was obtained in 47 % yield.

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Self-assembled porphyrin microrods and observation of structure-induced iridescence

Cited by 9 publications

References 31 publications

Versatile and Catalyst‐Free Methods for the Introduction of Group‐16 Elements at the meso‐Positions of Diarylporphyrins

Versatile and Catalyst‐Free Methods for the Introduction of Group‐16 Elements at the meso‐Positions of Diarylporphyrins

Focused ion beam processing and engineering of devices in self-assembled supramolecular structures

Synthesis of Steroid–Porphyrin Conjugates from Oestradiol, Oestrone, and Lithocholic Acid*

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