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Relevant academic research and scientific papers

Control of the aggregation properties of Tris(maltohexaose)-linked porphyrins with an alkyl chain

A series of porphyrins with three maltohexaose units and one alkyl chain (ethyl, butyl, hexyl, decyl, and hexadecyl) has been synthesized. Aggregation properties were investigated by absorbance and circular dichroism (CD) spectra. These trismaltohexaosylated tetraphenylporphyrins exhibited high water solubility. Although these porphyrins exhibited sharp Soret bands in DMSO solution, the Soret band broadened in a concentration-dependent manner in aqueous solution. This is the result of the aggregation of porphyrin molecules in aqueous solution. Interestingly, trismaltohexaosylated porphyrins with long alkyl chains of a certain length exhibited a broad. Soret band in water without concentration dependency due to the stability of such, aggregates. The CD spectra were silent in DMSO solution in all porphyrin derivatives, indicating that the maltohexaose moiety does not interact with the porphyrin chromophore in the monomelic state. However, in water, a splitting Cotton effect was observed at the Soret band. Intensity of this CD signal decreased as the length of the alkyl chain was extended. These observations show the formation of a chiral, face-to-face aggregate, in which the porphyrin rings are in close proximity to each other for short; alkyl chain derivatives. The porphyrin derivatives with long alkyl chains exhibit edge-to-edge aggregation, where hydrophobic interaction of the alkyl chains separates the porphyrin chromophores.

Novel liquid crystals consisting of tetraphenylporphyrine derivatives

Tetrakis(p-n-alkyloxyphenyl)porphyrin, 1, has been found to form mesophases with a wide range of temperature (from 45.3 to 144.5°C: 1a).

Synthesis of Porphyrin-CdSe Quantum Dot Assemblies: Controlling Ligand Binding by Substituent Effects

Cadmium selenide quantum dots of 2.2-2.3 nm diameter were prepared by phosphorus-free methods using oleic acid as stabilizing surface ligand. Ligand exchange monitored quantitatively by 1H NMR spectroscopy gave an estimate of 30-38 monodentate ligands per nanocrystal, with a ligand density of 1.8-2.3 nm-2. The extent of ligand exchange with macrocycles carrying one or more functional groups was investigated, with the aim of producing nanocrystal-macrocycle conjugates with a limited number of coligands. Metal-free porphyrins are able to sequester the Cd2+ ions from the Cd(oleate)2 outer layer of the nanocrystals. Zinc porphyrin complexes carrying one carboxylate function displace oleate efficiently to give porphyrin/CdSe composites with porphyrins stacked upright on the crystal surface. Porphyrins with four potential ligating sites are able to bind to the crystal surface only if the donors are at the end of sufficiently long and flexible tethers. High-dilution methods allowed the synthesis and isolation of well-defined composites of composition [CdSe{porphyrin}2], where porphyrin = 5,10,15,20-tetrakis{3-(carboxy-n-alkyloxy)phenyl}porphyrinato zinc (n = 5 or 10) and 5,10,15,20-tetrakis{3-(11-undecenyloxythiol)phenyl}-porphyrinato zinc. Comparison of the composition data obtained by 1H NMR spectroscopy with luminescence quenching behavior suggests a dependence of quenching efficiency on the tether length. Luminescence quenching was also observed for porphyrins that, according to 1H NMR results, do not undergo surface ligand exchange.

SYNTHESIS, EQUILIBRIUM SOLUBILITY, AND ELECTRONIC AND PMR SPECTRA OF meso-TETRA(ALKOXYPHENYL)PORPHYRINES

Tetra(alkoxyphenyl)porphines, readily soluble in nonpolar solvents, were synthesized from tetra(hydroxyphenyl)porphines.The equilibrium solubility was determined in hexane at 25 deg C, and its relation to the number of carbon atoms in the alkyl chain has