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Design, synthesis and structure of novel dendritic G-2 melamines comprising piperidine motifs as key linkers and 4-(n-octyloxy)aniline as a peripheral unit

Abstract : Starting from 4-amino-1-(tert-butoxycarbonyl)piperidine (Boc-PD-NH2), we report the synthesis of three novel meta-tri- and dimeric tetravalent N-substituted melamines with piperidin-4-yl groups. These compounds were used as central building-blocks and successfully incorporated into three new G-2 melamine dendrimers containing 4-(n-octyloxy)aniline as a peripheral unit. From a structural point of view, the challenging reactivity of Boc-PD-NH2 in comparison with 1-Boc-piperazine and cyclohexylamine, as SN2-Ar amination reagents against cyanuric chloride, was interpreted in terms of DFT (Density Functional Theory) thermodynamic and electronic computed data. Two out of the three dendrimers self-assembled in the solid state as large homogeneously packed spherical nano-aggregates (average D values ranging between 2500 and 3200 nm, TEM (Transmission Electron Microscopy) data) as a result of their “shell-to-shell” pre-associations in solution (DMF and 1,4-dioxane), promoted by chiral self-organisation, “round”- or “oval”-vaulted shapes (DFT data).
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https://hal.univ-reims.fr/hal-02490516
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Submitted on : Tuesday, February 25, 2020 - 11:36:17 AM
Last modification on : Tuesday, January 4, 2022 - 6:08:28 AM

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Carmen Sacalis, Cristina Morar, Pedro Lameiras, Alexandru Lupan, Radu Silaghi-Dumitrescu, et al.. Design, synthesis and structure of novel dendritic G-2 melamines comprising piperidine motifs as key linkers and 4-(n-octyloxy)aniline as a peripheral unit. Tetrahedron, Elsevier, 2019, 75 (35), pp.130468. ⟨10.1016/j.tet.2019.130468⟩. ⟨hal-02490516⟩

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