Erratum to “A convenient preparation of 2,3,5,6-tetrafluoro-4-iodo-benzaldehyde and its application in porphyrin synthesis” [J. Fluorine Chem. 125 (2004) 1379–1382]

Leroy, Jacques; Schöllhorn, Bernd; Syssa-Magalé, Jean-Laurent; Boubekeur, Kamal; Palvadeau, P.

doi:10.1016/j.jfluchem.2004.09.030

Cited by 10 publications

(13 citation statements)

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“…The synthesis and characterization of 3-(2-amino-4-methylpyrimidin-6-yl)pyridine 1 , 4-(2-amino-4-methylpyrimidin-6-yl)pyridine 2 , and 1-(2-amino-4-methylpyrimidin-6-yl)-2-(3-methoxypyridin-5-yl)ethyne 3 are reported elsewhere 17,18. 2,3,5,6-Tetrafluoro-4-iodobenzaldehyde and 2,3,5,6-tetrafluoro-4-bromo-benzaldehyde were synthesized following previously published methods 19. Melting points were determined on a Fisher-Johns melting point apparatus and are uncorrected.…”

Section: Methodsmentioning

confidence: 99%

Supramolecular Synthesis Based on a Combination of Hydrogen and Halogen Bonds

Aakeröy

Schultheiss

Rajbanshi

et al. 2008

Crystal Growth & Design

151

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A family of supramolecular reagents containing two different binding sites, pyridine and aminopyrimidine, were allowed to react with iodo-or bromo-substituted benzoic acids in order to assemble individual molecules into larger architectures with precise intermolecular interactions, using a combination of hydrogen-and halogen-bonds. The hydrogen-bond based amino-pyrimidine/ carboxylic acid or amino-pyrimidinium/carboxylate synthons are responsible for the assembly of the primary structural motif in every case (7/7 times, 100% supramolecular yield), while I⋯N, Br⋯N, and I⋯O, halogen bonds play a structural supporting role by organizing these supermolecules into extended 1-D and 2-D architectures (5/7 times, 71% supramolecular yield). These results illustrate how two different non-covalent interactions can be employed side-by-side in the reliable construction of extended molecular solid-state networks with predictable connectivity and dimensionality.

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Section: Methodsmentioning

confidence: 99%

Supramolecular Synthesis Based on a Combination of Hydrogen and Halogen Bonds

Aakeröy

Schultheiss

Rajbanshi

et al. 2008

Crystal Growth & Design

151

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“…The UV spectra of the perfluorinated X-C 6 F 4 -CH CH-C 6 F 4 -CN series (25)(26)(27) as well as the partial fluorinated X-C 6 F 4 -CH CH- C 6 H 4 -CN (19)(20)(21) analogues showed a hypsochromic shift (blue shift) compared to the H-homologues X-C 6 H 4 -CH CH-C 6 H 4 -CN (16)(17)(18). In contrast, the series X-C 6 H 4 -CH CH-C 6 F 4 -CN (22)(23)(24) showed a bathochromic shift (red shift) compared to the Hhomologues (16)(17)(18).…”

Section: Heck Approach (Methods C)mentioning

confidence: 99%

“…For the preparation of 2,3,5,6-tetrafluoro-4-iodo-benzaldehyde 9, we followed the method published in a recent paper [20] (Scheme 4).…”

Section: Preparation Of Hwe Precursorsmentioning

confidence: 99%

“…Molecules form parallel chains aligned by short CNÁ Á ÁH bonds (2.499 Å ), building antiparallel 2D networks through FÁ Á ÁH bonds (2.559 Å , 2.628 Å and 2.633 Å ). All these D-HÁ Á ÁA hydrogen bonds create (see graph-set) several rings and infinite chains like R2,2(8), R2,2(20), R4,2(12), R4,4(20), C1,1(12), C2,1 (14), C2,2(10), C2,2(12), C2,2 (14), C2,2(16) and C2,2 (20). The molecular planes are stacked by short FÁ Á ÁF (2.857 Å ) and CÁ Á ÁF (3.090 Å ) and show an interplanar distance of 3.340 Å .…”

Section: (E)-4-(4-iodo-2356-tetrafluorostyryl)-benzonitrile 21mentioning

confidence: 99%

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Preparation of donor–acceptor substituted fluorostilbenes and crystal chemistry of fluorinated (E)-4-(4-halogeno-styryl)-benzonitriles

Mariaca

Labat

Behrnd

et al. 2009

Journal of Fluorine Chemistry

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“…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

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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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Erratum to “A convenient preparation of 2,3,5,6-tetrafluoro-4-iodo-benzaldehyde and its application in porphyrin synthesis” [J. Fluorine Chem. 125 (2004) 1379–1382]

Cited by 10 publications

References 0 publications

Supramolecular Synthesis Based on a Combination of Hydrogen and Halogen Bonds

Supramolecular Synthesis Based on a Combination of Hydrogen and Halogen Bonds

Preparation of donor–acceptor substituted fluorostilbenes and crystal chemistry of fluorinated (E)-4-(4-halogeno-styryl)-benzonitriles

Directed synthesis of a halogen-bonded open porphyrin network

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