Herringbone Infinite Networks Formed by Terpyridine and Haloperfluoroarene Modules

4′-(4-Methylphenyl)-2,2′:6′,2″-terpyridine (1) self-assembles with dihaloperfluoroarenes (2). A chemo- and site-selective supramolecular synthesis occurs which preserves in the solid cocrystal the most stable s-trans, s-trans conformation of the pure terpyridine module. The single crystal X-ray structure of 3a, prepared from 1 and 1,4-diiodotetrafluorobenzene (2a) (monoclinic, a = 14.608(1), b = 13.276(1), c = 13.970(2) Å, β = 109.808(8)°, U = 2549.4 (4) Å3, T = 291 (1) K, space group C2/c Z = 4; μ(Mo-Kα) = 2.519 mm−1; d calc.: 1.890 g cm−3; 5748 reflections measured, 3715 unique (Rint = 0.024) which were used in all calculations; the final R and wR (F 2) were 0.043 and 0.069, respectively) shows the presence of infinite ribbons where the two modules alternate in a zigzag arrangement.