Thiophene α-Chain-End-Functionalized Oligo(2-methyl-2-oxazoline) as Precursor Amphiphilic Macromonomer for Grafted Conjugated Oligomers/Polymers and as a Multifunctional Material with Relevant Properties for Biomedical Applications.

Autor: Bendrea AD; Centre of Advanced Research in Bionanoconjugates and Biopolymers, 'PetruPoni' Institute of Macromolecular Chemistry, 41 A, Grigore-GhicaVoda Alley, 700487 Iasi, Romania., Cianga L; Centre of Advanced Research in Bionanoconjugates and Biopolymers, 'PetruPoni' Institute of Macromolecular Chemistry, 41 A, Grigore-GhicaVoda Alley, 700487 Iasi, Romania., Ailiesei GL; NMR Spectroscopy Department, 'PetruPoni' Institute of Macromolecular Chemistry, 41 A, Grigore-GhicaVoda Alley, 700487 Iasi, Romania., Göen Colak D; Department of Chemistry, Faculty of Science and Letters, Istanbul Technical University, Maslak, 34469 Istanbul, Turkey., Popescu I; Department of Natural Polymers, Bioactive and Biocompatible Materials, 'PetruPoni' Institute of Macromolecular Chemistry, 41 A, Grigore-GhicaVoda Alley, 700487 Iasi, Romania., Cianga I; Centre of Advanced Research in Bionanoconjugates and Biopolymers, 'PetruPoni' Institute of Macromolecular Chemistry, 41 A, Grigore-GhicaVoda Alley, 700487 Iasi, Romania.
Jazyk: angličtina
Zdroj: International journal of molecular sciences [Int J Mol Sci] 2022 Jul 06; Vol. 23 (14). Date of Electronic Publication: 2022 Jul 06.
DOI: 10.3390/ijms23147495
Abstrakt: Because the combination of π-conjugated polymers with biocompatible synthetic counterparts leads to the development of bio-relevant functional materials, this paper reports a new oligo(2-methyl-2-oxazoline) (OMeOx)-containing thiophene macromonomer, denoted Th-OMeOx . It can be used as a reactive precursor for synthesis of a polymerizable 2,2'-3-OMeOx-substituted bithiophene by Suzuki coupling. Also a grafted polythiophene amphiphile with OMeOx side chains was synthesized by its self-acid-assisted polymerization (SAAP) in bulk. The results showed that Th-OMeOx is not only a reactive intermediate but also a versatile functional material in itself. This is due to the presence of 2-bromo-substituted thiophene and ω-hydroxyl functional end-groups, and due to the multiple functionalities encoded in its structure (photosensitivity, water self-dispersibility, self-assembling capacity). Thus, analysis of its behavior in solvents of different selectivities revealed that Th-OMeOx forms self-assembled structures (micelles or vesicles) by "direct dissolution".Unexpectedly, by exciting the Th-OMeOx micelles formed in water with λ abs of the OMeOx repeating units, the intensity of fluorescence emission varied in a concentration-dependent manner.These self-assembled structures showed excitation-dependent luminescence as well. Attributed to the clusteroluminescence phenomenon due to the aggregation and through space interactions of electron-rich groups in non-conjugated, non-aromatic OMeOx, this behavior certifies that polypeptides mimic the character of Th-OMeOx as a non-conventional intrinsic luminescent material.
Databáze: MEDLINE
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