Unexpected Substituent Effects in Face-to-Face π-Stacking Interactions

2003 ◽  
Vol 107 (41) ◽  
pp. 8377-8379 ◽  
Author(s):  
Mutasem Omar Sinnokrot ◽  
C. David Sherrill
Keyword(s):  
Substituent Effects ◽  
Stacking Interactions ◽  
Face To Face ◽  
Π Stacking

Synthesis and crystal structure of a novel prochiral ketoimine: (E)-acetophenoneO-diphenylphosphoryl oxime

2015 ◽  
Vol 71 (3) ◽  
pp. 181-184
Author(s):  
Sean H. Majer ◽  
Joseph M. Tanski
Keyword(s):  
Crystal Structure ◽  
Solid State ◽  
Stacking Interactions ◽  
Synthesis And Crystal Structure ◽  
X Ray ◽  
Face To Face ◽  
Π Stacking

A novel activated prochiral ketoimine, (E)-acetophenoneO-diphenylphosphoryl oxime, C20H18NO2P, with an electron-withdrawing substituent on the imine N atom similar to other prochiral ketoimines, has been synthesized and the X-ray crystal stucture determined. The molecules pack together in the solid stateviaweak intermolecular C—H...O interactions and both face-to-face and edge-to-face π-stacking interactions.

scholarly journals Substituent Effects in Parallel-Displaced π-π Stacking Interactions: Distance Matters

2017 ◽  
Vol 56 (37) ◽  
pp. 11252-11257 ◽  
Author(s):  
Leslie-Joana Riwar ◽  
Nils Trapp ◽  
Bernd Kuhn ◽  
François Diederich
Keyword(s):  
Substituent Effects ◽  
Stacking Interactions ◽  
Π Stacking

Formation of dimers of inclusion cryptand/paraquat complexes driven by dipole–dipole and face-to-face π-stacking interactions

2004 ◽  
pp. 2670-2671 ◽  
Author(s):  
Feihe Huang ◽  
Liang Zhou ◽  
Jason W. Jones ◽  
Harry W. Gibson ◽  
Mehdi Ashraf-Khorassani
Keyword(s):  
Stacking Interactions ◽  
Face To Face ◽  
Π Stacking

scholarly journals Substituent Effects in the Crystal Packing of Derivatives of 4′-Phenyl-2,2′:6′,2″-Terpyridine

Crystals ◽  
2019 ◽  
Vol 9 (2) ◽  
pp. 110 ◽  
Author(s):  
Y. Klein ◽  
Alessandro Prescimone ◽  
Mariia Karpacheva ◽  
Edwin Constable ◽  
Catherine Housecroft
Keyword(s):  
Hydrogen Bonding ◽  
Crystal Packing ◽  
Substituent Effects ◽  
Molecular Structures ◽  
Solution Nmr ◽  
X Ray Diffraction ◽  
Aromatic Rings ◽  
Face To Face ◽  
Π Stacking ◽  
Derivatives Of

We report the preparation of a series of new 4′-substituted 2,2′:6′,2″-terpyridines: 4′-(3,5-dimethylphenyl)-2,2′:6′,2″-terpyridine (2), 4′-(3-fluoro-5-methylphenyl)-2,2′:6′,2″-terpyridine (3), 4′-(3,5-difluorophenyl)-2,2′:6′,2″-terpyridine (4), and 4′-(3,5- bis(trifluoromethyl)phenyl)-2,2′:6′,2″-terpyridine (5). The compounds have been characterized by mass spectrometry, solid-state IR spectroscopy and solution NMR and absorption spectroscopies. The single-crystal X-ray diffraction structures of 3, 5 and 6·EtOH (6 = 4′-(3,5-bis(tert-butyl)phenyl)-2,2′:6′,2″-terpyridine) have been elucidated. The molecular structures of the compounds are unexceptional. Since 3 and 5 crystallize without lattice solvent, we are able to understand the influence of introducing substituents in the 4′-phenyl ring and compare the packing in the structures with that of the previously reported 4′-phenyl-2,2′:6′,2″-terpyridine (1). On going from 1 to 3, face-to-face π-stacking of pairs of 3-fluoro-5-methylphenyl rings contributes to a change in packing from a herringbone assembly in 1 with no ring π-stacking to a layer-like packing. The latter arises through a combination of π-stacking of aromatic rings and N…H–C hydrogen bonding. On going from 3 to 5, N…H–C and F…H–C hydrogen-bonding is dominant, supplemented by π-stacking interactions between pairs of pyridine rings. A comparison of the packing of molecules of 6 with that in 1, 3 and 5 is difficult because of the incorporation of solvent in 6·EtOH.

The engineering of stilbazolium/iodocuprate hybrids with optical/electrical performances by modulating inter-molecular charge transfer among H-aggregated chromophores

2020 ◽  
Vol 7 (6) ◽  
pp. 1451-1466 ◽  
Author(s):  
Wei Wu ◽  
Xiang-Ling Lin ◽  
Qian Liu ◽  
Yan He ◽  
You-Ren Huang ◽  
...  
Keyword(s):  
Charge Transfer ◽  
Stacking Interactions ◽  
Face To Face ◽  
Electrical Bistability ◽  
Π Stacking ◽  
Molecular Charge

Good electrical bistability performances in stilbazolium/iodocuprate hybrids stem from the better face-to-face π⋯π stacking interactions induced by the substituents with appropriate lengths and electronic natures.

Long-Living Emitting Electrochemical Cells Based on Supramolecular π-π Interactions

2009 ◽  
Vol 1197 ◽  
Author(s):  
Rubén D. Costa ◽  
Enrique Ortí ◽  
Stefan Graber ◽  
Markus Neuburger ◽  
Catherine E. Hausecroft ◽  
...  
Keyword(s):  
Electrochemical Cells ◽  
Stacking Interactions ◽  
Light Emitting ◽  
Stacking Interaction ◽  
Face To Face ◽  
Π Interactions ◽  
Π Stacking ◽  
Π Stacking Interaction

AbstractThe complex [Ir(ppy)2(dpbpy)][PF6] (Hppy = 2-phenylpyridine, dpbpy = 6,6'-diphenyl-2,2'-bipyridine) has been prepared and evaluated as an electroluminescent component for light-emitting electrochemical cells (LECs). The complex exhibits two intramolecular face-to-face π-stacking interactions and long-lived LECs have been constructed; the device characteristics are not significantly improved in comparison to analogous LECs with 6-phenyl-2,2'-bipyridine with only one π-stacking interaction.

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