Synthesis of Polydiacetylene Charge-Transfer Complexes

Phelps, Dustin; Crihfield, April; Hartwell, Joshua; Hanks, Timothy W.; Pennington, William T.; Bailey, Rosa D.

doi:10.1080/10587250008023646

Cited by 8 publications

(6 citation statements)

References 7 publications

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“…[16,31] Also, this alkene has been cocrystallized with various diacetylenic molecules in the hope of obtaining host-guest complexes in which the diacetylenic fragments are suitably oriented for topochemical polymerization. [32,33] Halogen bonding involving haloalkynes has been studied in both the solid state and solution. Various complexes between 1-halo-2-phenylacetylenes and halide ions have been prepared, and the structures and stoichiometries of these complexes were found to depend on the nature of the halide ion and type of organic cation.…”

Section: Introductionmentioning

confidence: 99%

“…[11] The I···N distance reported herein is slightly shorter than those observed previously in complexes of TIE with nitrogen bases. [16,32,33] The only exceptions are 1,2-bis(4-pyridyl)ethylene·TIE (2.840 ) [16] and 1,4-bis(3-quinolyl)-1,3-butadiyne·TIE (2.884 ). [33] The centroid···cent-roid distance between two adjacent imidazole rings in one stack is 4.795 , and the angle between the centroid···cent-roid vector and the ring normal is 50.18.…”

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confidence: 97%

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Molecular Assemblies from Imidazolyl‐Containing Haloalkenes and Haloalkynes: Competition between Halogen and Hydrogen Bonding

Bouchmella

Boury

Dutremez

et al. 2007

Chemistry A European J

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The structural characterization of molecular assemblies constructed from imidazolyl-containing haloalkenes and haloalkynes is reported. 1-(3-Iodopropargyl)imidazole (2) and 1-(2,3,3-triiodoallyl)imidazole (5) were synthesized from 1-propargylimidazole (1). In the solid state, these wholly organic modules self-assemble through N...I halogen-bonding interactions, thus giving rise to polymeric chains. The N...I interaction observed in 2 (d(N...I)=2.717 A, angle-spherical C(sp)-I...N=175.8 degrees) is quite strong relative to previously reported data. The N...I interaction in 5 (d(N...I)=2.901 A, angle-spherical C(sp2)-I...N=173.6 degrees) is weaker, in accordance with the order C(sp)-X<--base>C(sp2)-X<--base. Compound 5 was found to give a 1:1 cocrystal 4 with morpholinium iodide (6). In the X-ray crystal studies of 4, N...I halogen-bonding interactions similar to those observed in 5 were shown not to be present, as the arrangement of the molecules is governed by two interwoven hydrogen-bonding networks. The first network involves N-H...O interactions between nearby morpholinium cations, and the second network is based on N-H...N hydrogen bonding between morpholinium cations and imidazolyl groups. Both hydrogen-bonding schemes are charge-assisted. Halogen bonding is not completely wiped out, however, as the triiodoalkene fragment forms a halogen bond with an iodide anion in its vicinity (d(I...I)=3.470 A, angle-spherical C(sp2)-I...I=170.7 degrees). X-ray crystal studies of 6 show a completely different arrangement from that observed in 4, namely, N-H...O interactions are not present. In crystalline 6, morpholinium cations are interconnected through C-H...O bridges (d(H...O)=2.521 and 2.676 A), and the NH2+ groups interact with nearby iodide anions (d(H...I)=2.633 and 2.698 A).

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Section: Introductionmentioning

confidence: 99%

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confidence: 97%

Molecular Assemblies from Imidazolyl‐Containing Haloalkenes and Haloalkynes: Competition between Halogen and Hydrogen Bonding

Bouchmella

Boury

Dutremez

et al. 2007

Chemistry A European J

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“…[84][85][86][87] In contrast, the supramolecular chemistry of 2,6-bis(arylethynyl)pyridines has received little attention, perhaps in part due to the scarcity of uniting the fields of molecule/ion recognition with the synthesis of highly-conjugated, carbon-rich materials. Most of the host/guest studies reported have focused on exploiting the pyridine lone pair to bind metal ion, 88 or organoiodides. 85 Alternatively, we hypothesized that the unique absorption/ emission properties of arylethynylpyridines in tandem with their structural rigidity aptly position them to function as small molecule or ion receptors.…”

Section: 6-bis(arylethynyl)pyridine-based Receptorsmentioning

confidence: 99%

Arylethynyl receptors for neutral molecules and anions: emerging applications in cellular imaging

et al. 2010

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This critical review will focus on the application of shape-persistent receptors for anions that derive their rigidity and optoelectronic properties from the inclusion of arylethynyl linkages. It will highlight a few of the design strategies involved in engineering selective and sensitive fluorescent probes and how arylacetylenes can offer a design pathway to some of the more desirable properties of a selective sensor. Additionally, knowledge gained in the study of these receptors in organic media often leads to improved receptor design and the production of chromogenic and fluorogenic probes capable of detecting specific substrates among the multitude of ions present in biological systems. In this ocean of potential targets exists a large number of geometrically distinct anions, which present their own problems to the design of receptors with complementary binding for each preferred coordination geometry. Our interest in targeting charged substrates, specifically how previous work on receptors for cations or neutral guests can be adapted to anions, will be addressed. Additionally, we will focus on the design and development of supramolecular arylethynyl systems, their shape-persistence and fluorogenic or chromogenic optoelectronic responses to complexation. We will also examine briefly how the “chemistry in the cuvet” translates into biological media.

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“…Our studies of halogen bonding have focused on cataloging supramolecular synthons involving a wide variety of halogen bonding acceptors, including nitrogen, − sulfur, , selenium, iodide, and more recently triiodide anions . Phosphorus should also be a good candidate as a halogen-bonding acceptor due to the softness of the phosphorus atom .…”

Section: Introductionmentioning

confidence: 99%

Phosphorus···Iodine Halogen Bonding in Cocrystals of Bis(diphenylphosphino)ethane (dppe) and p-Diiodotetrafluorobenzene (p-F₄DIB)

Siegfried

Arman

Kobra

et al. 2020

Crystal Growth & Design

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Three new cocrystals of bis(diphenylphosphino)ethane (dppe) and p-diiodotetrafluorobenzene (p-F4DIB) were studied using single-crystal X-ray crystallography. Two polymorphs containing a 1:1 dppe:p-F4DIB ratio were obtained, each displaying strong P···I halogen bonding along steplike chains. Additionally, a cocrystal with a 1:3 dppe:p-F4DIB ratio was studied. This cocrystal displays a similar main steplike chain to the 1:1 cocrystals, with pendant p-F4DIB molecules along the chain. In all three of the cocrystals, face-to-face and face-to-edge interactions involving both the phenyl rings and the perfluorobenzene rings contribute to the packing of the halogen bonded chains. Computational studies, including Hirshfeld surface analysis and ab initio calculations, were conducted to further elucidate the varying factors contributing to the packing of the cocrystals and the resulting structural stability.

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Synthesis of Polydiacetylene Charge-Transfer Complexes

Cited by 8 publications

References 7 publications

Molecular Assemblies from Imidazolyl‐Containing Haloalkenes and Haloalkynes: Competition between Halogen and Hydrogen Bonding

Molecular Assemblies from Imidazolyl‐Containing Haloalkenes and Haloalkynes: Competition between Halogen and Hydrogen Bonding

Arylethynyl receptors for neutral molecules and anions: emerging applications in cellular imaging

Phosphorus···Iodine Halogen Bonding in Cocrystals of Bis(diphenylphosphino)ethane (dppe) and p-Diiodotetrafluorobenzene (p-F₄DIB)

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Synthesis of Polydiacetylene Charge-Transfer Complexes

Cited by 8 publications

References 7 publications

Molecular Assemblies from Imidazolyl‐Containing Haloalkenes and Haloalkynes: Competition between Halogen and Hydrogen Bonding

Molecular Assemblies from Imidazolyl‐Containing Haloalkenes and Haloalkynes: Competition between Halogen and Hydrogen Bonding

Arylethynyl receptors for neutral molecules and anions: emerging applications in cellular imaging

Phosphorus···Iodine Halogen Bonding in Cocrystals of Bis(diphenylphosphino)ethane (dppe) and p-Diiodotetrafluorobenzene (p-F4DIB)

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Phosphorus···Iodine Halogen Bonding in Cocrystals of Bis(diphenylphosphino)ethane (dppe) and p-Diiodotetrafluorobenzene (p-F₄DIB)