Pentaerythritol tetrakis(4-iodo-2,3,5,6-tetrafluorophenyl) ether: a tecton for the self-assembly of double strand 1D infinite chains

Guido, Emanuela; Metrangolo, Pierangelo; Panzeri, Walter; Pilati, Tullio; Resnati, Giuseppe; Ursini, Maurizio; Logothetis, Thomas A.

doi:10.1016/j.jfluchem.2004.09.025

Cited by 20 publications

(6 citation statements)

References 119 publications

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“…The thermal behavior was determined by simultaneous DTA/TG analyses exemplarily for the coordination polymers ∞ 1 [Nd 2 Cl 6 (dpe) 2 (thz) 4 ]·dpe ( 2 ), ∞ 1 [GdCl 3 (dpe)(py) 2 ]·(dpe/py) ( 3 ), ∞ 1 [DyCl 3 (dpe)(thz) 2 ]·(dpe/thz) ( 8 ) and ∞ 1 [HoCl 3 (dpe)(thz) 2 ]·thz ( 11 ). Knowledge of melting and boiling points of dpe (mp = 150–153 °C and bp = 334 °C), thiazole (mp = −31 °C, bp = 117–118 °C) and pyridine (bp = 114 °C) allows assignment of the differential thermal analysis (DTA)/thermogravimetric (TG) signals of the compounds. All investigated compounds show rather similar thermal behavior with three defined mass losses around 150, 340, and 500 °C, indicating related transformation and decomposition processes.…”

Section: Resultsmentioning

confidence: 99%

Near-Infrared Luminescence and Inner Filter Effects of Lanthanide Coordination Polymers with 1,2-Di(4-pyridyl)ethylene

et al. 2016

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A series of 12 lanthanide coordination polymers was synthesized from anhydrous LnCl 3 and 1,2-di(4-pyridyl)ethylene (dpe) under solvothermal conditions in either thiazole (thz) or pyridine (py). The reactions yielded ∞ 1 [Ln 2 Cl 6 (dpe) 2 (thz) 4 ]•dpe with Ln = Ce (1), Nd (2), ∞ 1 [LnCl 3 (dpe)(py) 2 ]•(dpe/py) with Ln = Gd (3), Er (4), and ∞ 1 [LnCl 3 (dpe) (thz) 2 ](dpe/thz) with Ln = Sm (5), Gd (6), Tb (7), Dy (8), Er (9), Yb (10), as well as ∞ 1 [HoCl 3 (dpe)(thz) 2 ]•thz (11) and ∞ 2 [La 2 Cl 6 (dpe) 3 (py) 2 ]•dpe ( 12). One-dimensional coordination polymers (CPs) and a two-dimensional network of five different constitutions are formed by connection of LnCl 3 units via dpe molecules. As free ligand, dpe shows an excimer effect that is reduced in the coordination polymers. In addition, dipyridylethylene proves to be a suitable sensitizer for the photoluminescence of lanthanides in the near-infrared region (NIR) only. Thereby, dpe differs from the related ligand 1,2-di(4-pyridyl)ethane. For the compounds presented, four different luminescence effects were detected: luminescence based on fluorescence of the linker dpe is observed in the visible region, whereas ligand-sensitized 4f−4f NIR emission is dominating for trivalent Nd, Er, and Yb. The Er-containing CPs show an inner-filter effect of Er 3+ , which is based on reabsorption of emission of dpe triggering the erbium NIR emission.

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Section: Resultsmentioning

confidence: 99%

Near-Infrared Luminescence and Inner Filter Effects of Lanthanide Coordination Polymers with 1,2-Di(4-pyridyl)ethylene

et al. 2016

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“…It is also worth noting that the self-assembled structure of adsorbed bpe shows a surprising thermal stability, with a monolayer melting point of 414 K compared to the bulk melting point of 423-426 K [20]. This is lower than the bulk melting point by a factor of 0.97.…”

Section: Discussionmentioning

confidence: 96%

The monolayer structure of 1,2-bis(4-pyridyl)ethylene physisorbed on a graphite surface

Brewer¹,

Friščić²,

Day³

et al. 2012

Molecular Physics

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The crystalline monolayer of 1,2-bis(4-pyridyl)ethylene physisorbed on a graphite surface at 0.44 monolayers coverage has been observed and characterized by synchrotron X-ray diffraction and differential scanning calorimetry. The experimentally determined monolayer structure has p2 symmetry with lattice parameters a ¼ 17.77 Å , b ¼ 13.69 Å and ¼ 39.7 � . The unit cell contains two molecules, which are oriented in a plane parallel to the surface. It is proposed that the molecules are arranged such that they are able to form a weak C-H � � � N hydrogen bond between pyridine groups. The monolayer melts at 414 K, which is unusually close to the bulk melting point for a sub-monolayer coverage system. This molecule is chiral when adsorbed on the surface, but both isomers appear in the unit cell leading to no overall chirality in the monolayer.

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“…Among these compounds, substituted iodotetrafluorobenzenes proved to be particularly effective to orient substrates in crystal engineering by intramolecular π–π stacking interaction and intermolecular halogen bonding in supramolecular assemblies with pyridine derivatives . When employing a stoichiometric amount of the Metrangolo and Resnati's templating tecton 4 a (Figure ), the hydrogenated macrocyclic architecture 2 a was obtained in 76 % yield (Table , entry 4). This result suggests that 4 a can act as an exotemplate to orient two pyridine molecules by halogen bonding in the solution.…”

Section: Figurementioning

confidence: 99%

A Halogen‐Bond Donor Catalyst for Templated Macrocyclization

et al. 2019

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A halogen-bond templated 1:1 macrocyclization in solution is reported. Tetra(iodoperfluorophenyl) ethers were used as halogenbonded exotemplates in a substoichiometric amount (5 mol%). Pyridine-containing macrocyclic architectures were formed by ruthenium-catalyzed tandem metathesis/transfer hydrogenation sequence using sodium borohydride and methanol as nondihydrogen hydrogen source. The halogen-bonded stabilization energies were analyzed relying on density functional theory.

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Pentaerythritol tetrakis(4-iodo-2,3,5,6-tetrafluorophenyl) ether: a tecton for the self-assembly of double strand 1D infinite chains

Cited by 20 publications

References 119 publications

Near-Infrared Luminescence and Inner Filter Effects of Lanthanide Coordination Polymers with 1,2-Di(4-pyridyl)ethylene

Near-Infrared Luminescence and Inner Filter Effects of Lanthanide Coordination Polymers with 1,2-Di(4-pyridyl)ethylene

The monolayer structure of 1,2-bis(4-pyridyl)ethylene physisorbed on a graphite surface

A Halogen‐Bond Donor Catalyst for Templated Macrocyclization

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