Crystal structures of three 4-substituted-2,2'-bipyridines synthesized by Sonogashira and Suzuki-Miyaura cross-coupling reactions.

Luong Thi Thu, Thuy ORCID: 0000-0001-6597-7742, Nguyen Bich, Ngan, Nguyen, Hien and Van Meervelt, Luc ORCID: 0000-0003-2186-5209 (2017) Crystal structures of three 4-substituted-2,2'-bipyridines synthesized by Sonogashira and Suzuki-Miyaura cross-coupling reactions. Acta crystallographica. Section E, Crystallographic communications, 73 (Pt 4). pp. 610-615.

Text Crystal structures of three 4-substituted-2,2'-bipyridines synthesized by Sonogashira and Suzuki-Miyaura cross-coupling reactions.pdf - Published version Download (792kB) | Preview

Abstract

Facile synthetic routes for three 4-substituted 2,2'-bi-pyridine derivatives, 4-[2-(4-methyl-phenyl)-ethyn-yl]-2,2'-bi-pyridine, C₁₉H₁₄N₂, (I), 4-[2-(pyridin-3-yl)ethyn-yl]-2,2'-bi-pyridine, C₁₇H₁₁N₃, (II), and 4-(indol-4-yl)-2,2'-bi-pyridine, C₁₈H₁₃N₃, (III), <i>via</i> Sonogashira and Suzuki-Miyaura cross-coupling reactions, respect-ively, are described. As indicated by X-ray analysis, the 2,2'-bi-pyridine core, the ethyl-ene linkage and the substituents of (I) and (II) are almost planar [dihedral angles between the two ring systems: 8.98 (5) and 9.90 (6)° for the two mol-ecules of (I) in the asymmetric unit and 2.66 (14)° for (II)], allowing π-conjugation. On the contrary, in (III), the indole substituent ring is rotated significantly out of the bi-pyridine plane [dihedral angle = 55.82 (3)°], due to steric hindrance. The crystal packings of (I) and (II) are dominated by π-π inter-actions, resulting in layers of mol-ecules parallel to (30-2) in (I) and columns of mol-ecules along the <i>a</i> axis in (II). The packing of (III) exhibits zigzag chains of mol-ecules along the <i>c</i> axis inter-acting through N-H⋯N hydrogen bonds and π-π inter-actions. The contributions of unknown disordered solvent mol-ecules to the diffraction intensities in (II) were removed with the SQUEEZE [Spek (2015 ▸). <i>Acta Cryst.</i> C<b>71</b>, 9-18] algorithm of <i>PLATON</i>. The given chemical formula and other crystal data do not take into account these solvent mol-ecules.

Item Type:	Article
Uncontrolled Keywords:	2,2′-bi­pyridine, Sonogashira cross-coupling, Suzuki–Miyaura cross-coupling, crystal structure, dye-sensitized solar cells, palladium-catalyzed
Depositing User:	Symplectic Admin
Date Deposited:	29 May 2019 15:41
Last Modified:	19 Jan 2023 00:42
DOI:	10.1107/s2056989017004662
Related URLs:	Author Publisher
URI:	https://livrepository.liverpool.ac.uk/id/eprint/3043328