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Fluorescent EDOT-Functionalized Poly-E-Caprolactone: Synthesis, Photophysical and Self-Assembling Properties in Organic Solvents and Its Serendipitously Noticed Behaviour in Protonated Media
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1  "Petru Poni" Institute of Macromolecular Chemistry, Iasi, Romania


In the last few years several fluorescent poly-e- caprolactones [1-3] were designed, synthesized and subsequently used as nanoparticles [1], nanofibers [2] or scaffolds [3] in various prospective bioapplications. Meanwhile, our interest was directed toward electro - and photoactive moieties - functionalized poly/or oligo-e- caprolactone, that worked as key building blocks (macromonomers) for new grafted conjugated polymers or hybrid systems successfully used as biosensors [4,5] or regenerative medicine [6]. In the same line, the present report is aimed to extend the investigations and to highlight the properties in solution (photophysical, self-assembling) of 3, 4-ethylenedioxythiophene-functionalized poly-e- caprolactone (EDOT-PCL) synthesized by ring-opening polymerization (ROP). The results of the studies in two organic solvents (chloroform and acetonitrile), having different selectivity in relation with the constitutive parts of EDOT-PCL, revealed its propensity for self-assembling, proved by Dynamic Light Scattering (DLS) measurements, while fluorescent emission maxima in the range 310-430 nm, depending on the solvent were evidenced, as well. Moreover, its capability for spontaneous oxidant-free oligomerization, presumably due to and under the action of acidic character of CDCl3, serendipitously noticed during 13C-NMR registration, was subsequently validated by experiments performed in chloroform in the presence of hydrochloric acid. This is an interesting and applications-oriented useful observation which supports that recently demonstration of oxidant-free polymerization of common EDOT in the only presence of some organic acids [7] could also be extended to EDOT-containing more complex structure.

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Keywords: fluorescent nanoparticles; self-assembly; EDOT; oxidant-free polymerization
Comments on this paper
Ana Maria Diez-Pascual
Comment on 10.3390/CGPM2020-07208
Very nice article. Did you characterize them in environmentally friendly solvents?
First of all thank you for the interest in our presentation and nice word. For the moment we didn't investigate the behavior of our macromonomer in another solvents as chloroform and ACN. More specifically in for example more friendly ( green) methyl -THF. This compound was used previously for electro-copolymerization with EDOT-MeOH in the aim to improve the biocompatibility of an flexible and 3D PP mesh platform, as it is mentioned in the references of the Abstract. But it is a good idea and we will do it in the future.
Sincerely yours,