Abstract
The preparation and characterization of 4′-(4-n-octyloxyphenyl)-3,2′:6′,3″-terpyridine (8) and 4′-(4-n-nonyloxyphenyl)-3,2′:6′,3″-terpyridine (9) are reported. The single crystal structures of 4′-(4-n-hexyloxyphenyl)-3,2′:6′,3″-terpyridine (6), 4′-(4-n-heptyloxyphenyl)-3,2′:6′,3″-terpyridine (7), and compounds 8 and 9 have been determined. The conformation of the 3,2′:6′,3″-tpy unit is trans,trans in 6 and 7, but switches to cis,trans in 8 and 9. This is associated with significant changes in the packing interactions with a more dominant role for van der Waals interactions between adjacent n-alkyloxy chains and C–Hmethylene... π interactions in 8 and 9. The solid-state structures of 6 and 7 with the n-hexyloxy and n-heptyloxy chains feature interwoven sheets of supramolecular assemblies of molecules, with pairs of n-alkyloxy chains threaded through cavities in an adjacent sheet.
Highlights
The coordination chemistry of 2,20 :60,200 -terpyridine is well established, and is dominated by tpy acting as a bis-chelating ligand [1,2,3,4,5]
The terpyridine isomers 3,20 :60,300 -tpy and 4,20 :60,400 -tpy (Scheme 1a) are growing in popularity as building blocks in coordination polymers owing to the vectorial properties of the outer pyridine N-donors, and the fact that the central pyridine ring is coordinatively innocent [6,7,8]
Considering the near-planar conformers, conformation III in Scheme 1a is ideally suited to the formation of discrete [2 + 2] metallocycles, this has only been structurally confirmed in a few cases [9,10]
Summary
The coordination chemistry of 2,20 :60 ,200 -terpyridine (tpy) is well established, and is dominated by tpy acting as a bis-chelating ligand [1,2,3,4,5]. 2020.1 [14] reveals 95 entries for the 3,20 :60 ,300 -tpy motif, both in free ligands, protonated ligands, and metal coordination compounds Leaving aside those structures in which the. The CSD contains the solid-state structures of only nine free and non-protonated 3,20 :60 ,300 -tpy ligands. Ligands we report the syntheses and conformation is influenced by the length of the 4-n-alkyloxy motivated us to look 6, at 7, the characterizations of compounds. We report the syntheses and and 9, and we discuss the factors that lead to a switch from conformation I to II as the n-alkyloxy chain characterizations of compounds 8 and 9 (Scheme 1b) and the crystal structures of compounds 6, 7, 8 increases in length.
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