Supramolecular interactions of carbon nanotubes with biosourced polyurethanes from 2-(2,5-dimethyl-1H-pyrrol-1-yl)-1,3-propanediol

Galimberti, Maurizio; Barbera, Vincenzina; Citterio, Attilio; Sebastiano, Roberto; Truscello, Ada; Valerio, Antonio; Conzatti, Lucia; Mendichi, Raniero

doi:10.1016/j.polymer.2015.02.042

Cited by 17 publications

(47 citation statements)

References 39 publications

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“…The polymeric nature of graphene layer with the six atoms aromatic ring as the repeating unit is responsible for such exceptional properties. Hence, main objectives of graphene synthesis [8][9][10][11][12] and functionalization [8,[13][14][15][16][17][18][19][20][21][22][23] are to obtain and preserve such structure.…”

Section: Introductionmentioning

confidence: 99%

“…In our research group, sustainable synthesis of a pyrrole derivative was obtained [51,52], based on the reaction of primary amine with diketone in the absence of any solvent and catalyst. 2-(2,5-Dimethyl-1H-pyrrol-1-yl)-1,3-propanediol (serinol pyrrole, SP) was obtained from the reaction of 2-amino-1,3-propandiol (known as serinol) with 2,5-hexanedione (HD).…”

Section: Introductionmentioning

confidence: 99%

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Facile and sustainable functionalization of graphene layers with pyrrole compounds

Barbera

Bernardi

Palazzolo

et al. 2017

Pure and Applied Chemistry

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A facile and sustainable functionalization of graphene layers was performed with pyrrole compounds (PyC) prepared through the Paal-Knorr reaction of a primary amine with 2,5-hexanedione. A good number of primary amines were used: hexanamine, dodecanamine, octadecanamine, 2-aminoacetic acid, 2-amino-1,3-propanediol, 3-(triethoxysilyl)propan-1-amine. The reactions were characterized by good yield, up to 96 %, and indeed satisfactory atom efficiency, up to 80 %. The functionalization of graphene layers was obtained by mixing PyC with a high surface area graphite and heating at a temperature range from 130 °C to 150 °C for 3 h. The yield of functionalization reaction was larger than 60 % and also up to about 90 % for the pyrrole compounds from dodecanamine and 2-amino-1,3-propanediol, respectively. The cycloaddition reaction between the graphene layers and the pyrrole compound, oxidized in two position, is proposed as working hypothesis to account for such efficient functionalization. Raman spectroscopy revealed that the structure of the graphitic substrate remained substantially unaltered, after the reaction. Stable dispersions of HSAG adducts with different PyC were prepared in solvents with different solubility parameters and HRTEM analysis showed the presence of aggregates of only few layers of graphene. Qualitative results of dispersion tests were used to calculate the Hansen sphere for the HSAG adduct with the pyrrole compound based on dodecanamine so to provide a first estimate of its Hansen solubility parameters. This work paves the way for the facile and sustainable modification of the solubility parameters of graphene layers and for the predictive assessment of their compatibility with different environments.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Facile and sustainable functionalization of graphene layers with pyrrole compounds

Barbera

Bernardi

Palazzolo

et al. 2017

Pure and Applied Chemistry

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“…The synthesis of SP, summarized in Figure 2, is described in detail in the experimental part and has been discussed elsewhere [32,33]. In brief, serinol (S) was first reacted with 2,5-hexanedione (HD), adopting the Paal-Knorr reaction, obtaining the tricyclic compound 4a,6a-dimethyl-hexahydro-1,4-dioxa-6b-azacyclopenta[cd]pentalene (HHP), that was then converted into SP.…”

Section: Synthesis Of 2-(25-dimethyl-1h-pyrrol-1-yl)-13-propanediolmentioning

confidence: 99%

“…Pyrrole can give rise to π-π stacking with aromatic compounds such as CNT and the hydroxyl groups allow the preparation of polymers such as polyethers by step-growth polymerization. First example of polymer obtained by step-growth polymerization, polyurethane, has been recently reported [33]. In this manuscript, polyethers from the reaction of SP with 1,6-dibromohexane are reported.…”

Section: Introductionmentioning

confidence: 97%

“…In recent papers, polymers from serinol have been reported: cyclic carbonates derivatives were converted into polymers through organocatalytic ring opening polymerization [30] and a compound obtained from the reaction of serinol with succinimidyl ester of trimethyl-locked benzoquinone was used to prepare water soluble biodegradable polyester [31]. In this work, serinol chemoselectivity was exploited [32][33][34], preparing SP through the Paal-Knorr reaction [34,35] of serinol (S) with 2,5-hexanedione (HD), performing the reaction in the absence of solvents and catalysts. SP has been defined as a Janus molecule [36], that means a molecule with two faces and, hence, a dual reactivity.…”

Section: Introductionmentioning

confidence: 99%

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Polyether from a biobased Janus molecule as surfactant for carbon nanotubes

Barbera¹,

Musto²,

Citterio³

et al. 2016

Express Polym. Lett.

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Abstract.A new polyether (PE) was prepared from a biobased Janus molecule, 2-(2,5-dimethyl-1H-pyrrol-1-yl)-1,3-propanediol (serinol pyrrole, SP). SP was synthesized with very high yield (about 96%) and high atom efficiency (about 80%) by reacting a biosourced molecule, such as serinol, with 2,5-hexanedione in the absence of solvent or catalyst. The reaction of SP with 1,6-dibromohexane led to PE oligomers, that were used as surfactants for multiwalled carbon nanotubes (MWCNT), in ecofriendly polar solvents such as acetone and ethyl acetate. The synergic interaction of aromatic rings and oxyalkylene sequences with the carbon allotrope led to dramatic improvement of surfactant efficiency: only 24% of SP based PE was extracted with ethyl acetate from the adduct with MWCNT, versus 98% of a typical pluronic surfactant. Suspensions of MWCNT-PE adducts in ethyl acetate were stable for months. High resolution transmission electron microscopy revealed a film of oligomers tightly adhered to MWCNT surface.

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A Janus Molecule for Screen‐Printable Conductive Carbon Ink for Composites with Superior Stretchability

et al. 2023

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Inspired by decades of research in the compatibilization of fillers into elastomeric composites for high‐performance materials, a novel polyurethane‐based stretchable carbon ink is created by taking advantage of a Janus molecule, 2‐(2,5‐dimethyl‐1H‐pyrrol‐1‐yl)propane‐1,3‐diol (serinol pyrrole, SP). SP is used to functionalize the carbon and comonomer in the polymer phase. The use of SPs in both the organic and inorganic phases results in an improved interaction between the two phases. When printed, the functionalized material has a factor 1.5 lower resistance‐strain dependence when compared to its unfunctionalized analogue. This behavior is superior to commercially available carbon inks. To demonstrate the suitability of ink in an industrial application, an all‐printed, elastomer‐based force sensor is fabricated. This “pyrrole methodology” is scalable and broadly applicable, laying the foundation for the realization of printed functionalities with improved electromechanical performance.

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Supramolecular interactions of carbon nanotubes with biosourced polyurethanes from 2-(2,5-dimethyl-1H-pyrrol-1-yl)-1,3-propanediol

Cited by 17 publications

References 39 publications

Facile and sustainable functionalization of graphene layers with pyrrole compounds

Facile and sustainable functionalization of graphene layers with pyrrole compounds

Polyether from a biobased Janus molecule as surfactant for carbon nanotubes

A Janus Molecule for Screen‐Printable Conductive Carbon Ink for Composites with Superior Stretchability

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