Perfluorophenyl-phenyl interactions

In addition to hydrogen bonding, other types of noncovalent interactions, such as perfluorophenyl-phenyl interactions, are very well suited for self-assembly purposes. The perfluorinated cobalt phthalocyanine (F16Co5) molecules do not form an ordered structure when deposited on Au(lll) under UHV [131,132]. This disorder and the lack of submolecular resolution are in contrast to the behavior of the protonated complex, which is... 

Coates, G.W., Dunn, A.R., Henling, L.M., Dougherty, D.A. and Grubbs, R.H. (1997) Phenyl-perfluorophenyl stacking interactions a new strategy for supermolecule construction. Angew. 

Keywords [2+2]photodimerization, phenyl-perfluorophenyl stacking interaction... 

M. J. Marsella, Z. Q. Wang, R. J. Reid and K. Yoon, Synthesis of acetylenic cyclophanes via intramolecular self-assembly evidence of perfluorophenyl-phenyl quadrupole interactions in the solution state, Org. Lett, 3, 885-887 (2001). 

Marsella and coworkers exploited perfluorophenyl-phenyl quadrupole interactions to template the synthesis of a thiophene-containing cyclophane [44]. As shown in Scheme 6.14, when the oligomeric precursors 98-101 were treated with Sonogashira cross-coupling conditions, the mixed perfluorophenyl-phenyl cyclophane 102 was reproducibly achieved in greater yield than either of the symmetrical analogs 103 and 104. Other mixed macrocyclic derivatives were also prepared as part of this study, and their findings with these model systems supported... 

For example, Marder and co-workers [10] (among others) have studied liquid crystal mesophases induced by the presence of quadrupolar interactions between non-mesomorphic phenyl- and perfluorophenyl-containing moieties (e.g. 1). 

Analysis of the packing of the complexes (e.g. Fig. 13) also showed the absence of quadrupolar phenyl/perfluorophenyl interactions, an observation... 

The face-to-face stacking interaction between phenyl and perfluorophenyl groups was used to orient olefinic molecules and to cocrystallize them [51]. The... 

Fig. 2 The application of intramolecular substitution to control the [2 + 2] photodimerization in the solid state (a) phenyl-perfluorophenyl interactions between two stilbenes and (b) a J-shaped dicarboxylic acid that self-assembles to form a hydrogen-bonded assembly.

Vangala VR, Nangia A, Lynch VM (2002) Interplay of phenyl-perfluorophenyl stacking, C-H - F, C-F - jc and F - F interactions in some crystaUine aromatic azines. Chem Commun 1304-1305... 

Coates et al. used stacking interactions in the phenyl-perfluorophenyl system to direct co-crystal-lization of mixed stilbene and cinnamic acid co-crystals, thereby directing the formation of the mixed P-truxinic acid derivative in very high yield. Ito has recently reviewed the solid-state organic photochemistry of mixed crystals. " ... 

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