Synthesis of Pyrrolo[2,3- c ]isoquinolines via the Cycloaddition of Benzyne with Arylideneaminopyrroles: Photophysical and Crystallographic Study - Aix-Marseille Université Accéder directement au contenu
Article Dans Une Revue ACS Omega Année : 2019

Synthesis of Pyrrolo[2,3- c ]isoquinolines via the Cycloaddition of Benzyne with Arylideneaminopyrroles: Photophysical and Crystallographic Study

Résumé

An efficient and quick access toward a series of (E)-2-arylideneaminopyrroles 6 and to their benzyne-promoted aza-Diels−Alder cycloaddition products is provided. These products are three pyrrolo[2,3-c]isoquinolines 8a−c substituted in position 5 with different electron-acceptor (A) or electron-donor (D) aryl groups. Intermediates and products were obtained in good yields (up to 78 and 84%, respectively), and their structures were determined on the basis of NMR measurements and HRMS analysis. Photophysical properties of 8a−c were investigated, finding good Stokes shift in different solvents, but only the product 8c showed appreciable fluorescence intensity since its 5-aryl group (2,4-Cl 2 Ph) could favor the twisted intramolecular charge transfer effect. In addition, a riveting relationship between solvent viscosity and fluorescence intensity was found. Structures of 6 and 8 were studied and confirmed by single-crystal X-ray diffraction, observing that their electronic distributions effect the supramolecular assembly but with only long-distance hydrophobic interactions. A CE-B3LYP model was used to study the energetic topology and understand the crystal architecture of compounds as well as find a connection with both the synthetic and photophysical results.

Domaines

Chimie organique
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Dates et versions

hal-02354816 , version 1 (07-11-2019)

Identifiants

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Juan-Carlos Castillo, Alexis Tigreros, Yoann Coquerel, Jean Rodriguez, Mario Macías, et al.. Synthesis of Pyrrolo[2,3- c ]isoquinolines via the Cycloaddition of Benzyne with Arylideneaminopyrroles: Photophysical and Crystallographic Study. ACS Omega, 2019, 4 (17), pp.17326-17339. ⟨10.1021/acsomega.9b02043⟩. ⟨hal-02354816⟩

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