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: Anca-Dana Bendrea, Luminita Cianga, Gabriela-Liliana Ailiesei, Demet Göen Colak, Irina Popescu, Ioan Cianga
Jazyk: angličtina
Rok vydání: 2022
Předmět:
Zdroj: International Journal of Molecular Sciences, Vol 23, Iss 14, p 7495 (2022)
Druh dokumentu: article
ISSN: 1422-0067
1661-6596
06431208
DOI: 10.3390/ijms23147495
Popis: 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 λabs 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.
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