Halogen bonding and isostructurality in 2,4,6‐tris(2‐halophenoxy)‐1,3,5‐triazines

Abstract

Crystal structures of 2,4,3, chloro, bromo, iodo;

Ab initio calculations on halogen‐bonded complexes and comparison with density functional methods

“…Indeed, most of the energetic and structural features found in hydrogen‐bonded complexes are reproduced in halogen‐bonded complexes as well. Owing to its strength, selectivity, and directivity, halogen bonding has led to a number of applications in fields, as diverse as molecular recognition, enantiomers's separation, crystal engineering, and supramolecular architectures 2–28. In particular, the utilization of this specific interaction in the context of drug design is nowadays coming to light clearly 3, 29–35.…”

Symmetry-controlled rearrangements in Piedfort Units (PU) of 2,4,6-triaryloxy-1,3,5-triazines

“…In 3-IPOT, they stabilise the molecular stacking around the C 3 axes like iron hoops, while with ortho-substitution exemplified by 2-FPOT (LIKKUM) [25], the six F atoms would be crammed in the 'inward' diads. To avoid collision, they generate such a repulsion which separates the 'outward' PUs parallel to the 1,3,5-triazine rings by D = 4.78 Å .…”

“…In the course of our study on semirigid 2,4,6-triaryloxy-1,3,5-triazines [18] (Scheme 1) (nR-POT; n = 2, 3, 4 and R = F, Cl, Br, I, Me) found in the literature [19][20][21][22][23][24][25], we recognised [26] a mistake in the assignment of D 3 symmetry to POT confused with relaxed form of C 3(g) found in 4-BrPOT [21]. Thus, three PU-diads (the stacked diads formed by 2,4,6-triaryloxy-1,3,5-triazines in crystalline state are called Piedfort Units [27]) can be distinguished according to their symmetries C 3(g) , C 3i and D 3 ( (ii) 4-BrPOT has a hexagonal dimorph (HEXWIQ); (iii) it is isostructural with 2,4,6-tris(4-chlorophenoxy)-1,3,5-triazine (4-ClPOT, VALQEE), common space group P6 3 /m; and (iv) in clathrates via two real ncr's (180°, 60°), induced by the guest molecules, it assumes space group R 3 (Fig.…”

Novel Host–Guest Structures of 2,4,6-Tris(4-Halophenoxy)-1,3,5-Triazines(XPOT): Inclusion of C60 and Pyridine

“…The para-substituted 2,4,6-tris(4-halophenoxy)-1,3,5-triazines (4-XPOT, X = Cl, Br, I; or XPOT for short) are known to form many types of host-guest structures which may be classified as either channel or cavity architectures: For co-crystals with ClPOT as host molecule only channels structures are known, IPOT provides cavities and BrPOT forms both channels and cavities. In contrast, the ortho and meta-substituted analogues form closed packed structures without guests [1]. More recently, the meta-fluorination of 4-BrPOT has produced an alternative channel architecture enclosing various guest molecules [2].…”