Competition between hydrogen bonding and arene–perfluoroarene stacking. X-Ray diffraction and molecular simulation on 5,6,7,8-tetrafluoro-2-naphthoic acid and 5,6,7,8-tetrafluoro-2-naphthamide crystals

Cozzi, Franco; Bacchi, Sergio; Filippini, G.; Pilati, Tullio; Gavezzotti, Angelo

doi:10.1039/b820791g

Cited by 24 publications

(20 citation statements)

References 27 publications

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“…becomes less important, or almost optional''. 4 This means, the pure p-p F -overlap transforms into a p F -p F and p-p-overlap, which are less favourable but still energetically stabilizing. 2 However, the existence of p-p F -stacking is not generally excluded whenever hydrogen bonds are present in the crystal.…”

Section: Introductionmentioning

confidence: 99%

Organic fluorine compounds: a great opportunity for enhanced materials properties

et al. 2011

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Interactions of "organic fluorine" have gained great interest not only in the context of crystal engineering, but also in the systematic design of functional materials. The first part of this tutorial review presents an overview on interactions known by organic fluorine. This involves π-π(F), C-F···H, F···F, C-F···π(F), C-F···π, C-F···M(+), C-F···C=O and anion-π(F) interactions, as well as other halogen bonds. The effect of the exchange of H vs. F is discussed by means of several examples and a short introduction to the young field of "fluorous" chemistry is given. The second part is dedicated to numerous applications of fluorine and fluorous interactions. It is shown how application of fluorination is used to enable a number of reactions, to improve materials properties and even open up new fields of research.

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Section: Introductionmentioning

confidence: 99%

Organic fluorine compounds: a great opportunity for enhanced materials properties

et al. 2011

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“…Fluorine is the most electronegative element and can be used as an excellent hydrogenbond acceptor. A wide variety of research activities have been undertaken on fluorous compounds, which exhibit a significant role in generating different types of supramolecular structures throughstacking, C-HÁ Á ÁF-C, FÁ Á ÁF and C-FÁ Á Á intermolecular interactions (Berger et al, 2011;Cozzi et al, 2009;D'Oria & Novoa, 2008;Asensio et al, 2006). In most cases,stacking and C-HÁ Á ÁF-C interactions occur and stabilize the structures of the fluorous compounds.…”

Section: Introductionmentioning

confidence: 99%

Two cadmium(II) fluorous coordination compounds tuned by different bipyridines

et al. 2017

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Fluorine is the most electronegative element and can be used as an excellent hydrogen-bond acceptor. Fluorous coordination compounds exhibit several advantageous properties, such as enhanced high thermal and oxidative stability, low polarity, weak intermolecular interactions and a small surface tension compared to hydrocarbons. C-H...F-C interactions, although weak, play a significant role in regulating the arrangement of the organic molecules in the crystalline state and stabilizing the secondary structure. Two cadmium(II) fluorous coordination compounds formed from 2,2'-bipyridine, 4,4'-bipyridine and pentafluorobenzoate ligands, namely catena-poly[[aqua(2,2'-bipyridine-κN,N')(2,3,4,5,6-pentafluorobenzoato-κO)cadmium(II)]-μ-2,3,4,5,6-pentafluorobenzoato-κO:O'], [Cd(CFO)(CHN)(HO)], (1), and catena-poly[[diaquabis(2,3,4,5,6-pentafluorobenzoato-κO)cadmium(II)]-μ-4,4'-bipyridine-κN:N'], [Cd(CFO)(CHN)(HO)], (2), have been synthesized solvothermally and structurally characterized. Compound (1) shows a one-dimensional chain structure composed of Cd-O coordination bonds and is stabilized by π-π stacking and O-H...O hydrogen-bond interactions. Compound (2) displays a one-dimensional linear chain structure formed by Cd-N coordination interactions involving the 4,4'-bipyridine ligand. Adjacent one-dimensional chains are extended into two-dimensional sheets by O-H...O hydrogen bonds between the coordinated water molecules and adjacent carboxylate groups. Moreover, the chains are further linked by C-H...F-C interactions to afford a three-dimensional network. In both structures, hydrogen bonding involving the coordinated water molecules is a primary driving force in the formation of the supramolecular structures.

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“…A key example of a molecule that did not follow this pattern was molecule 4, in which intramolecular hydrogen bonding between the hydroxyl groups in the ortho position on the terminal phenylene rings and the carbonyl groups of the terephthalate, similar to those shown by Zhao and coworkers to promote OPE coplanairty, [68,69] out-competed the arene-perfluoroarene cofacial interactions and yielded a highly planar backbone ( Figure 10). [70] The sensitivity of conformation of this class of molecules highlighted for us that the shallow potential energy well of rotation about the PE linkage-on the order of 1 kcal/mol-allows control of conformation through balancing non-covalent interactions. [71] Along these lines, our group demonstrated reproducible and sensitive piezochromism (a change in color upon exertion of mechanical force) and mechanofluorochromism (a change in color of fluorescence upon exertion of mechanical force) of solids of 5, an analog of 3 with octyloxy terminal groups (Figure 11).…”

Section: Side Chain/main Chain Aromatic Interactions That Dictate Conmentioning

confidence: 99%

Stimuli-responsive side chains for new function from conjugated materials

Thomas

Pawle

Smith

2016

Journal of Photochemistry and Photobiology A: Chemistry

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This article describes several projects in our laboratory relating to stimuliresponsive conjugated materials using functional side chain moieties. Although side chain engineering has become increasingly important in controlling the packing of conjugated materials, these groups have typically been reserved for imparting solubility to otherwise insoluble materials. By incorporating solubilizing side chains through photocleavable nitrobenzyl linkers, new conjugated polymers behave as negative photoresists upon exposure to ultraviolet light with minimal photobleaching. Our approach enables photopatterning and solution-based fabrication of multilayer conjugated polymer films without the use of orthogonally soluble materials. Work to understand the electronic effects of the aromatic side chain substituents in these materials led to the subsequent discovery of aromatic interactions between side chains and main chains that control the conformations of solid-state phenylene-ethynylene oligomers, including highly twisted conjugated backbones. Such materials, when appropriately substituted, display reversible piezochromic and mechanofluorochromic behavior.

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Competition between hydrogen bonding and arene–perfluoroarene stacking. X-Ray diffraction and molecular simulation on 5,6,7,8-tetrafluoro-2-naphthoic acid and 5,6,7,8-tetrafluoro-2-naphthamide crystals

Cited by 24 publications

References 27 publications

Organic fluorine compounds: a great opportunity for enhanced materials properties

Organic fluorine compounds: a great opportunity for enhanced materials properties

Two cadmium(II) fluorous coordination compounds tuned by different bipyridines

Stimuli-responsive side chains for new function from conjugated materials

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