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From N -vinylpyrrolidone anions to modified paraffin-like oligomers via double alkylation with 1,8-dibromooctane: access to covalent networks and oligomeric amines for dye attachment

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ABSTRACT

The double alkylation of N-vinylpyrrolidone (N-VP) with 1,8-dibromooctane yields paraffin-like oligomeric chains bearing polymerizable vinyl moieties. These oligomers were radically crosslinked in bulk with N-VP as co-monomer yielding swellable polymer disks. The vinylic side groups of the N-VP oligomers allow thiol–ene click reactions with 2-aminoethanethiol hydrochloride to obtain reactive amino-functionalized oligomers. Further modification of the free amino groups with 1,4-difluoro-9,10-anthraquinone (DFA) yields red-colored oligomeric anthraquinone dyes. The final reaction of DFA-substituted N-VP oligomers with Jeffamine® M 600 leads to blue-colored and branched oligomers with poly(ethylene glycol) side chains.

No MeSH data available.


UV–vis spectra of oligomers 5 (c = 0.16 g/mL, red), 6 (c = 0.63 g/mL, blue) and DFA (c = 0.016 g/mL, grey).
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Figure 2: UV–vis spectra of oligomers 5 (c = 0.16 g/mL, red), 6 (c = 0.63 g/mL, blue) and DFA (c = 0.016 g/mL, grey).

Mentions: The second fluoro substituent of the attached anthraquinone moiety in 5 was replaced at elevated temperature with O-(2-aminopropyl)-O'-(2-methoxyethyl)propylene glycol (Jeffamine® M 600) yielding the branched blue-colored oligomeric dye 6. The deep blue color is a result of the presence of two amino groups in 1,4-position of the anthraquinone dye [44]. Thus, this reaction can also be followed with the naked eye. Furthermore, the conversion of oligomer 6 was verified with UV–vis spectroscopy (Fig. 2).


From N -vinylpyrrolidone anions to modified paraffin-like oligomers via double alkylation with 1,8-dibromooctane: access to covalent networks and oligomeric amines for dye attachment
UV–vis spectra of oligomers 5 (c = 0.16 g/mL, red), 6 (c = 0.63 g/mL, blue) and DFA (c = 0.016 g/mL, grey).
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Related In: Results  -  Collection

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Figure 2: UV–vis spectra of oligomers 5 (c = 0.16 g/mL, red), 6 (c = 0.63 g/mL, blue) and DFA (c = 0.016 g/mL, grey).
Mentions: The second fluoro substituent of the attached anthraquinone moiety in 5 was replaced at elevated temperature with O-(2-aminopropyl)-O'-(2-methoxyethyl)propylene glycol (Jeffamine® M 600) yielding the branched blue-colored oligomeric dye 6. The deep blue color is a result of the presence of two amino groups in 1,4-position of the anthraquinone dye [44]. Thus, this reaction can also be followed with the naked eye. Furthermore, the conversion of oligomer 6 was verified with UV–vis spectroscopy (Fig. 2).

View Article: PubMed Central - HTML - PubMed

ABSTRACT

The double alkylation of N-vinylpyrrolidone (N-VP) with 1,8-dibromooctane yields paraffin-like oligomeric chains bearing polymerizable vinyl moieties. These oligomers were radically crosslinked in bulk with N-VP as co-monomer yielding swellable polymer disks. The vinylic side groups of the N-VP oligomers allow thiol–ene click reactions with 2-aminoethanethiol hydrochloride to obtain reactive amino-functionalized oligomers. Further modification of the free amino groups with 1,4-difluoro-9,10-anthraquinone (DFA) yields red-colored oligomeric anthraquinone dyes. The final reaction of DFA-substituted N-VP oligomers with Jeffamine® M 600 leads to blue-colored and branched oligomers with poly(ethylene glycol) side chains.

No MeSH data available.