Kinetic Investigations on the Chiral Induction by Amino Acids in Porphyrin J-Aggregates

The self-assembling kinetics of the 5,10,15,20- (4-sulfonato-phenyl)porphyrin (TPPS ) into nano-tubular J-aggregates under strong acidic condition and in the presence of amino acids as templating chiral reagents have been investigated through UV/Vis spectroscopy. The ability of the chiral species to...

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Bibliographic Details
Published in:International journal of molecular sciences 2023-01, Vol.24 (2), p.1695
Main Authors: Zagami, Roberto, Castriciano, Maria Angela, Romeo, Andrea, Scolaro, Luigi Monsù
Format: Article
Language:English
Subjects:
Aggregates
aggregation kinetics
Amino Acids
Broken symmetry
chiral supramolecular assemblies
Chirality
Circular Dichroism
Dichroism
Endangered & extinct species
Extinction
Handedness
Hydrophobicity
J-aggregates
Polyamines
Porphyrins
Porphyrins - chemistry
Protocol
Reagents
Self-assembly
Spectrophotometry, Ultraviolet
Spectroscopy
Stereoisomerism
Symmetry
symmetry breaking
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Summary:The self-assembling kinetics of the 5,10,15,20- (4-sulfonato-phenyl)porphyrin (TPPS ) into nano-tubular J-aggregates under strong acidic condition and in the presence of amino acids as templating chiral reagents have been investigated through UV/Vis spectroscopy. The ability of the chiral species to transfer its chiral information to the final J-aggregate has been measured through circular dichroism (CD) spectroscopy and compared to the spontaneous symmetry breaking process usually observed in these nano-aggregates. Under the experimental conditions here selected, including mixing protocol, we have observed a large difference in the observed aggregation rates for the various amino acids, those with a positively charged side group being the most effective. On the contrary, these species are less efficient in transferring their chirality, exhibiting a quite low or modest enhancement in the observed dissymmetry g-factors. On the other side, hydrophobic and some hydrophilic amino acids are revealed to be very active in inducing chirality with a discrete increase of intensity of the detected CD bands with respect to the spontaneous symmetry breaking.
ISSN:1422-0067
1661-6596
1422-0067
DOI:10.3390/ijms24021695