Fluorescent Phthalocyanine Assembly Distinguishes Chiral Isomers of Different Types of Amino Acids and Sugars

Abstract

The functions of some natural supramolecular architectures, such as ribosomes, are dependent on the recognition of different types of chiral biomolecules. However, the recognition of different types of chiral molecules (multiobject chiral recognition), such as amino acids and sugars, by independent and identically artificial supramolecular assembly, was rarely achieved. In this article, simple amphiphilic achiral phthalocyanine was found to form supramolecular chiral assemblies with charged water-soluble polymers upon host-guest interactions at the air/water interface. Among these systems, one identical phthalocyanine/poly(l-lysine) assembly not only can distinguish enantiomers of different amino acids but also can recognize several epimers of monose. The chiral recognitions were achieved by comparing either the steady-state fluorescence intensity or fluorescence quenching rate of phthalocyanine/poly(l-lysine) assemblies, before and after interaction with different small chiral molecules. It was demonstrated that the interactions between poly(l-lysine) and different small chiral molecules could change the aggregation of phthalocyanines. And the sensitivity of fluorescence and the excellent multiobject chiral recognition properties of the phthalocyanine/poly(l-lysine) assembly are dependent on the subtle molecular packing mode and the cooperation of different noncovalent interactions.

Applications of Photoinduced Phenomena in Supramolecularly Arranged Phthalocyanine Derivatives: A Perspective

“…It has been suggested that D-glutamic acid could induce a more significant aggregation of the phthalocyanine molecules; in contrast, L-glutamic acid molecule contribute to slightly move away the macroring molecules. Further analysis by AFM, CD, and UV-Vis spectroscopy are consistent with these conclusions [52].…”

“…The positive charges in poly(l-lysine) corroborate the effective interaction existing with the phthalocyanine even at the air-water interface. Further AFM, XRD and FT-IR investigations [52] confirmed the origination of a weak chirality when films of the pure phthalocyanine were deposited; but, on the other side, the presence of poly(l-lysine) induces the handover of biomaterials chirality to the phthalocyanine coassemblies.…”

“…The crown-ether has a dual function: to induce amphiphilic properties and pliability to the macrocycle, while the other two components have to relocate optical activity to the co-assemblies. Such supramolecular assemblies have been fabricated by both the Langmuir-Blodgett (LB) [53,54] and the Langmuir-Schäfer (LS) techniques [52] since the Coulombic interaction between species with opposite charges allows the transfer of robust dyads; in this case with the presence of the amphiphilic phthalocyanine floating on the water surface and DNA or poly(l-lysine) dissolved in the subphase. The surface pressure vs. area per molecule curves already gave indications of the interaction at the air-water interface between the biomacromolecules and the phthalocyanine.…”

Supramolecular complexes based on liquid‐crystalline polysiloxanes and copper phthalocyanine

“…For SCP [CuPc]‐[P 2 ‐SO 3 ] (Fig. (b)), except for the peaks mentioned above, the significant difference was an additional peak appearing at 1420 cm −1 , assigned to the symmetric stretching vibrations of C  N bonds in CuPc . Furthermore, the peak at 3683 cm −1 was broader, indicating that the OH stretching vibration had been constrained under a strong intramolecular hydrogen bond, suggesting the monomer CuPc was connected to the SAPs.…”

Molecular enantiorecognition of l‐glucose and d‐glucose in whole blood samples

“…The stochastic mode is based on the principle of the reversible binding of an analyte to the wall of the pore. The metallophthalocyanines used for the design of the sensors were Copper(II)phthalocyanine and Nickel(II)phthalocyanine; the selection of these materials was made particularly due to their ability to form aggregates with channels, able to perform molecular enantiorecognition, 23 these materials presenting also electrical conductivity and oxidative catalytic activity. 20 Chiral selectors are of particular importance in biomedical enatioanalysis.…”