Self-assembly via (N⋯I) non-covalent bonds between 1,4-diiodo-tetrafluoro-benzene and a tetra-imino ferrocenophane

Syssa-Magalé, Jean-Laurent; Boubekeur, Kamal; Palvadeau, P.; Meerschaut, A.; Schöllhorn, Bernd

doi:10.1016/j.molstruc.2003.11.031

Cited by 23 publications

(16 citation statements)

References 15 publications

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“…Also the imine functionality attractively interacts with electrophilic halogens, and the XB is formed along the expected axis of the nitrogen lone pair. 180 …”

Section: Nature Of the Halogen Bondmentioning

confidence: 99%

“… 172 − 174 When carbonyl groups act as XB acceptors, the oxygen may function as both a monodentate 175 and a bidentate 176 site, and the XB donor(s) are pinned in a trigonal planar geometry. Sulfonyl 177 , 178 and phosphoryl 179 groups behave similarly to carbonyl moieties, and also imines 180 form XBs along the respective n-pair axis. XBs around ethers, 56 , 181 thioethers, 182 , 183 and amines 184 , 185 usually adopt a tetrahedral arrangement with preferential axial directions for the XBs around hexacyclic amines 186 and equatorial directions for hexacyclic thioethers 64 ( Figure 14 ).…”

Section: Introductionmentioning

confidence: 99%

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The Halogen Bond

et al. 2016

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The halogen bond occurs when there is evidence of a net attractive interaction between an electrophilic region associated with a halogen atom in a molecular entity and a nucleophilic region in another, or the same, molecular entity. In this fairly extensive review, after a brief history of the interaction, we will provide the reader with a snapshot of where the research on the halogen bond is now, and, perhaps, where it is going. The specific advantages brought up by a design based on the use of the halogen bond will be demonstrated in quite different fields spanning from material sciences to biomolecular recognition and drug design.

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“…Also the imine functionality attractively interacts with electrophilic halogens, and the XB is formed along the expected axis of the nitrogen lone pair. 180 …”

Section: Nature Of the Halogen Bondmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

The Halogen Bond

et al. 2016

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“…[29][30][31][32][33][34] Various useful crystal materials can be designed using XB including temperature-sensitive, magnetic, or optically crystalline materials. [35][36][37][38][39][40][41][42][43][44] XB has also a vast potential in the design of soft materials such as liquid crystals, [45][46][47][48] polymers, 38,49 and gels. 50 In the present article, the possibility of finding minima in gas phase for halogen bonded systems with the same sign has been explored in both cation-cation and anion-anion clusters.…”

Section: Introductionmentioning

confidence: 99%

Cation–cation and anion–anion complexes stabilized by halogen bonds

Quiñonero

Alkorta

Elguero

2016

Phys. Chem. Chem. Phys.

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Stable minima showing halogen bonds between charged molecules with the same sign have been explored by means of theoretical calculations. The dissociation transition states and their corresponding barriers have also been characterized. In all cases, the results indicate that the complexes are thermodynamically unstable but kinetically stable with respect to the isolated monomers in gas phase. A corrected binding energy profile by removing the charge-charge repulsion of the monomers shows a profile similar to the one observed for the dissociation of analogous neutral systems. The nature of the interaction in the minima and TSs has been analyzed using the symmetry adapted perturbation theory (SAPT) method. The results indicate the presence of local favorable electrostatic interactions in the minima that vanish in the TSs. Natural bond orbital (NBO) and "atoms-in-molecules" (AIM) theories were used to analyze the complexes, obtaining good correlations between Laplacian and electron density values with both bond distances and charge-transfer energy contributions E(2). The largest E(2) orbital interaction energies for cation-cation and anion-anion complexes are 561.2 and 197.9 kJ mol, respectively.

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“…In previous work we have also used less rigid ferrocenophanes for the self-assembly directed by XB. 12 Neither our structure nor the more recently published study by Goldberg 3c,13 on halogen-bonded porphyrin assemblies have revealed any porous inclusion compounds. Taking into account these results, we chose a more directed approach for the present study.…”

mentioning

confidence: 54%

“…4c-e Among other groups, we have been studying in the past the self-assembly of I 2 -PFB and various nitrogen-and oxygen-containing XB acceptors. 12,15 We extended the nature of the XB donor by a tritopic (I 3 -PFB) 16 and a tetratopic (I 4 -PFTPP) 17 derivative, the latter being a porphyrin carrying four iodo-perfluorophenyl groups in the meso positions. The respective donor and acceptor molecules have been co-crystallized and the resulting adduct structures were resolved by single-crystal X-ray diffraction as described in the footnote (Table S1 †).…”

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confidence: 99%

Directed synthesis of a halogen-bonded open porphyrin network

et al. 2014

Self Cite

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A strategy for the elaboration of a halogen-bonded porphyrin network is reported. The progressive introduction of geometric constraints via the modulation of building blocks and self-assembly via strong and directional halogen bonding led successfully to the construction of an open porphyrin network with nano-sized tubular channels.Based on the chemical and structural diversity of molecular building blocks one can nowadays control to a certain degree the self-assembly process in order to systematically alter the composition, topology and functionality of molecular materials. However, the search for porous solids remains an important topic and new strategies for the construction of extended framework architectures are longed for. 1,2 Porphyrins and their metal complexes are particularly useful building blocks because of their thermal and chemical stability and their square planar geometry and multidentate functionality. Since 1990, many groups have been working successfully on the development of porphyrin framework solids. 3 These assemblies are mainly based on thermodynamically labile interactions such as metal coordination, hydrogen bonding or π-π stacking. More recently, non-covalent halogen bonding (XB) has proven to be an alternative powerful tool in crystal engineering. 4,5 The resulting materials promise interesting potential applications in shape-and size-selective sorption (storage and molecular sieves), chemical sensing or catalysis. 4 A recent IUPAC recommendation 6 defines XB, a special case of σ-hole bonding, 7 as a non-covalent attractive interaction involving halogens as electron density acceptors. In analogy to hydrogen bonding, the halogenated binding partner is designated the XB donor, and the involved Lewis base the corresponding XB acceptor. A striking characteristic of this particular interaction is its unambiguous unidirectionality rendering crystal engineering more predictable in the absence of other competitive strong interactions. Only a few examples of porous supramolecular materials are known that are based on XB as the predominant interaction. Besides cage structures, 8 particularly interesting and challenging is certainly the elaboration of open networks containing channels accessible to solvents. Relatively weak type II XB between halogen atoms (C-X⋯X-C) afforded hexagonal channel clathrates. 8a,9 In more recent approaches the self-assembly process was mainly governed by strong and linear C-X⋯A interactions (A = Lewis base). 10,11 The strategy of Rissanen and Metrangolo 11 involved the alignment of cyclophane cavities capable of complexing small solvent molecules such as chloroform or methanol. In previous work we have also used less rigid ferrocenophanes for the self-assembly directed by XB. 12 Neither our structure nor the more recently published study by Goldberg 3c,13 on halogen-bonded porphyrin assemblies have revealed any porous inclusion compounds. Taking into account these results, we chose a more directed approach for the present study. 14 We systematically varied the topicit...

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Self-assembly via (N⋯I) non-covalent bonds between 1,4-diiodo-tetrafluoro-benzene and a tetra-imino ferrocenophane

Cited by 23 publications

References 15 publications

The Halogen Bond

The Halogen Bond

Cation–cation and anion–anion complexes stabilized by halogen bonds

Directed synthesis of a halogen-bonded open porphyrin network

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