Über Pyromellitsäure‐ und Cumidinsäure‐Derivate. V. Teil

Hopff, H.; Doswald, P.; Manukian, B. K.

doi:10.1002/hlca.19610440507

Cited by 12 publications

(7 citation statements)

References 12 publications

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“…The published procedure to synthesize the key building block, 1 , was simplified by combining steps and minimizing purification (Scheme , see Supporting Information for details). Durene was consecutively brominated in near quantitative yield in one pot to 1,4-dibromo-2,3,5,6-tetrakis(bromomethyl)benzene 2 , which was oxidized to the tetracarboxylic acid 3 , and then directly dehydrated/sublimed to afford dianhydride 4 .…”

Section: Resultsmentioning

confidence: 99%

Pyromellitic Diimide-Based Donor–Acceptor Poly(phenylene ethynylene)s

Guo

Watson

2011

Macromolecules

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A series of donor–acceptor poly(phenylene ethynylene)s (PPEs) with N,N′-dialkylpyromellitic diimide (PMDI) as electron acceptor and various donor units are reported. Optoelectronic properties were investigated by UV/vis absorption and electrochemical measurements, revealing constant LUMO energies (∼−3.6 eV) across the series with HOMO energy levels governed by the donor monomers and optical band gaps from 2.30 to 1.50 eV. With a high volume fraction of solubilizing side chains, the polymers are soluble in common organic solvents, but solution NMR measurements and thermochromism in solution indicate aggregation due to additive intermolecular interactions between donor and acceptor units.

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Section: Resultsmentioning

confidence: 99%

Pyromellitic Diimide-Based Donor–Acceptor Poly(phenylene ethynylene)s

Guo

Watson

2011

Macromolecules

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“…Elemental microanalyses were carried out by Dornis und Kolbe, Mikroanalytisches Laboratorium, Mülheim, Germany. The compounds C 6 H 2 (CH 2 Br) 4 -1,2,4,5, [Li{C 6 H(CH 2 NMe 2 ) 4 -2,3,5,6}] 2 ( 7 ), and C 6 Br 2 (CH 2 Br) 4 -2,3,5,6 ( 1 ) were prepared according to previously described methods.…”

Section: Methodsmentioning

confidence: 99%

Hypercoordinate Aryltrialkylsilanes and -stannanes and Their Use in the Synthesis of Homodinuclear Organometallic Complexes with a 1,4-Phenylene Bridge

Koten¹,

Steenwinkel²,

Jastrzebski³

et al. 1997

Organometallics

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New mono-and dinuclear aryltrialkylsilanes and-stannanes [Me 3 M{C 6 H 3 (CH 2 NMe 2) 2-2,6}] (M) Si (5), Sn (6)) and [(Me 3 M) 2-1,4-{C 6 (CH 2 NMe 2) 4-2,3,5,6}] (M) Si (9), Sn (10)) have been prepared from transmetalation reactions of dimeric [Li{C 6 H 3 (CH 2 NMe 2) 2-2,6}] 2 and new polymeric [Li 2-1,4-{C 6 (CH 2 NMe 2) 4-2,3,5,6}] ∞ with (trimethylsilyl)trifluoromethanesulfonate or trimethyltin chloride. The X-ray crystal structures of dinuclear 9 and 10 have been determined and in the molecular geometries found the central 1,4-phenylene dimetalated aryl ligand system provides bidentate C,N-coordination to silicon in 9 and terdentate pseudofacial N,C,N′-coordination to tin in 10. Reactions of the newly prepared silanes 5 and 9 and stannanes 6 and 10 with diverse palladium(II) and platinum(II) substrates afford organometallic products arising from both aryl and methyl group transfer. For example, the reaction of dinuclear stannane 10 (or dinuclear silane 9) with palladium(II) species gives the bimetallic complex [(PdCl) 2-1,4-{C 6 (CH 2 NMe 2) 4-2,3,5,6}] (15), whereas its reaction with [PtCl 2 (COD)] (COD) cycloocta-1,5-diene) or Me 3 SnCl gives the ionic tin(IV) species [(Me 2-Sn) 2-1,4-{C 6 (CH 2 NMe 2) 4-2,3,5,6}] 2+ (X-) 2 with X being Cl (18a) or Me 3 SnCl 2 (18b). The X-ray crystal structure of 18b has been determined and the molecular geometry found shows that the central dimetalated aryl ligand system provides terdentate meridional N,C,N′-coordination to both tin centers.

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“…The former are the main moieties involved in the binding and recognition of catecholamines. Receptor 1 was readily prepared in three steps from 1,4‐dibromo‐2,3,5,6‐tetrakis(bromomethyl)benzene 4 11 (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…Elemental analyses were taken on a Yanako MT‐6 CHN corder at the Center for Instrumental Analysis of Hokkaido University. 1,4‐Dibromo‐2,3,5,6‐tetrakis(bromomethyl)benzene ( 4 )11 and 2,3,5,6‐tetramethylterephthaloyl dichloride ( 7 )12 were prepared following the known procedures. All commercially available compounds were used without further purification unless otherwise indicated.…”

Section: Methodsmentioning

confidence: 99%

“…Tetraethyl 4,8‐dibromo‐1,2,3,5,6,7‐hexahydro ‐ s ‐indacene‐2,2,6,6‐tetracarboxylate (5) : An EtONa solution was prepared by dissolving Na metal (14.2 g, 617 mmol) in absolute EtOH (1.0 L). Diethyl malonate (49.1 g, 306 mmol) and then compound 4 11 (62.3 g, 103 mmol) were added. The reaction mixture was heated under reflux with stirring for 7 h under Ar, after which the solvent was removed under reduced pressure.…”

Section: Methodsmentioning

confidence: 99%

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Multipoint Recognition of Catecholamines by Hydrindacene‐Based Receptors Accompanied by the Complexation‐Induced Conformational Switching

Kawai

Katoono

Fujiwara

et al. 2005

Chemistry A European J

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The molecular recognition of catecholamines by hydrindacene-based receptors 1 and 2, as well as the durene-based receptor 3, and the guest-induced conformational changes are reported. These receptors selectively bind adrenaline and dopamine salts through the guests' ammonium group and 3-hydroxyl group on the aromatic ring. In the case of adrenaline, an additional hydrogen bond with a benzylic hydroxyl group is formed. In 2 % CD3CN/CDCl3, the association constants are of the order of 10(4) M(-1), which is much larger than with guests without the 3-hydroxyl groups (10(3) M(-1)). The two amide groups of receptor 1 can rotate freely around the C(aromatic)--C(amide) bond, whereas the tert-amide in 2 changes between two stable conformations at a slow enough rate to allow detection by (1)H NMR spectroscopy. In the absence of a guest molecule, the syn-conformer is less stable than the anti-conformer. On complex formation with adrenaline, the syn-conformer becomes dominant due to an intramolecular dipole-reversal effect in addition to multipoint hydrogen bonding.

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Über Pyromellitsäure‐ und Cumidinsäure‐Derivate. V. Teil

Cited by 12 publications

References 12 publications

Pyromellitic Diimide-Based Donor–Acceptor Poly(phenylene ethynylene)s

Pyromellitic Diimide-Based Donor–Acceptor Poly(phenylene ethynylene)s

Hypercoordinate Aryltrialkylsilanes and -stannanes and Their Use in the Synthesis of Homodinuclear Organometallic Complexes with a 1,4-Phenylene Bridge

Multipoint Recognition of Catecholamines by Hydrindacene‐Based Receptors Accompanied by the Complexation‐Induced Conformational Switching

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