A self-assembly study of PNA–porphyrin and PNA–BODIPY hybrids in mixed solvent systems

The synthesis and self-assembled nanostructures of a series of nucleopeptides (NPs) derived from the dipeptide Phe–Phe and the peptide nucleic acid unit which are covalently attached through an amide or a triazole linker are described. Depending on the variables such as protecting groups, linkers, and nucleobases, spherical nanoparticles were observed through scanning electron microscopy and high-resolution transmission electron microscopy images, and the porous nature of representative NPs was corroborated by carboxyfluorescein entrapment. Hydrophobic substituents on different sites of NPs and solvents employed for peptide self-assembly played a crucial role for corresponding morphologies. The stability of nanoparticles was also probed under external stimuli such as pH, temperature, and enzymatic hydrolysis using proteolytic enzymes. The semiconducting nature of the NP-modified carbon electrodes suggested their potential use as a new capacitor material.

show abstract

“…Porphyrin and BODIPY conjugates of PNA monomers have recently been reported as promising candidates for photocatalytic applications. 17…”

Section: Introductionmentioning

confidence: 99%

Self-Assembly of Diphenylalanine–Peptide Nucleic Acid Conjugates

2019

View full text Add to dashboard Cite

show abstract

“…Significant endeavors are focusing on preparing organized and specifically shaped chromophores for superior performance in molecular photonic devices such as artificial light harvesting systems . One of the most appealing methods for achieving such goals is the nature‐inspired self‐assembly via hydrogen bonding , .…”

Section: Methodsmentioning

confidence: 99%

Self‐Assembly of Simple Corroles, via Hydrogen Bonding and Coordination

et al. 2020

View full text Add to dashboard Cite

The unique properties of pyrazole raised the interest of preparing a corrole containing one such moiety on its C10 position. Its single‐crystal X‐ray structure uncovers it to be a dimer wherein the two monomeric units are held together by very strong corrole‐pyrazole NH···N hydrogen bonding interactions that lead to a very well self‐assembled network. The corresponding gallium(III) complex is isolated as a trimer in which all hydrogen bonding interactions are between the pyrazole subunits. In contrast, a tetrameric coordination complex is formed from the gallium(III) complex of a corrole with a pyridyl moiety on C10.

show abstract

“…Over the course of our studies focused on the development of amphiphilic porphyrin-based supramolecular systems, we largely used the "good-bad" solvent self-assembling method, by which macrocycles are at first molecularly dissolved in a good solvent and then a bad solvent is added to trigger the aggregation process. Operating carefully within the experimental parameters, i.e., concentration of porphyrin solutions, type, and order of addition of the two solvents and time, assemblies with different structures can be achieved [27,28]. We typically used ethanol/water or dimethylacetamide/water solvent combinations at proper water contents to drive the formation of ordered porphyrin suprastructures by hydrophobic effect [21,[29][30][31][32].…”

Section: Introductionmentioning

confidence: 99%

Amphiphilic Porphyrin Aggregates: A DFT Investigation

et al. 2019

View full text Add to dashboard Cite

Owing to the attractive potential applications of porphyrin assemblies in photocatalysis, sensors, and material science, studies presently concerning porphyrin aggregation are widely diffused.π-π stacking, H-bonding, metal coordination, hydrophobic effect, and electrostatic forces usually drive porphyrin interaction in solution. However, theoretical studies of such phenomena are still limited.Therefore, a computational examination of the different porphyrin aggregation approaches is proposed here, taking into account amphiphilic [5-{4-(3-trimethylammonium)propyloxyphenyl}-10,15,20-triphenylporphyrin] chloride, whose aggregation behavior has been previously experimentally investigated. Different functionals have been adopted to investigate the porphyrin dimeric species, considering long-range interactions. Geometry optimization has been performed, showing that for the compound under analysis, H-type and cation-π dimers are the most favored structures that likely co-exist in aqueous solution. Of note, frontier orbital delocalization showed an interesting interaction between the porphyrin units in the dimer at the supramolecular level.

show abstract

A self-assembly study of PNA–porphyrin and PNA–BODIPY hybrids in mixed solvent systems

Abstract: In this work a peptide nucleic acid has been covalently linked with porphyrin and boron-dipyrromethene exhibiting self assembly properties and light-harvesting capability.

Cited by 38 publications

References 34 publications

Self-Assembly of Diphenylalanine–Peptide Nucleic Acid Conjugates

Self-Assembly of Diphenylalanine–Peptide Nucleic Acid Conjugates

Self‐Assembly of Simple Corroles, via Hydrogen Bonding and Coordination

Amphiphilic Porphyrin Aggregates: A DFT Investigation

Contact Info

Product

Resources

About