Synthese, Flüssigkristallinität und Photochemie von Di- und Tristyrylbenzolen mit Alkoxyseitenketten / Synthesis, Liquid Crystals and Photochemistry of Di- and Tristyrylbenzenes with Alkoxy Side Chains

Zerban, Georg; Meier, Herbert

doi:10.1515/znb-1993-0208

Cited by 38 publications

(17 citation statements)

References 5 publications

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“…14 We thus developed a convergent synthetic approach to 3 based on Wittig-Horner coupling. The total synthesis involved 12 steps with a total yield of 30% (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and ¹¹C‐labelling of (E,E)‐1‐(3′,4′‐dihydroxystyryl)‐4‐(3′‐methoxy‐4′‐hydroxystyryl) benzene for PET imaging of amyloid deposits^†

Wang

Mathis

Huang

et al. 2002

Labelled Comp Radiopharmac

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SummaryCarboxylic acid derivatives of the amyloid-binding dye Congo red do not enter the brain well and are thus unable to serve as in vivo amyloid-imaging agents. A neutral amyloid probe, (E,E)-1-(3 0 ,4 0 -dihydroxystyryl)-4-(3 0 -methoxy-4 0 -hydroxystyryl)benzene (3), devoid of any carboxylate groups has been designed and synthesized via a 12-step reaction sequence with a total yield of 30%. The unsymmetric compound 3 has also been labelled with C-11 via [11 C]methyl iodide ([ 11 C]CH 3 I) methylation of a symmetric 4,4 0 -dimesyl protected precursor followed by deprotection. Preliminary evaluation indicated that compound 3 selectively stained plaques and neurofibrillary tangles in postmortem AD brain, and exhibited good binding affinity (K i =38 AE 8 nM) for Ab(1-40) fibrils in vitro. In vivo pharmacokinetic studies indicated that [ 11 C]3 exhibited higher brain uptake than its carboxylic acid analogs and good clearance from normal control mouse brain.

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“…14 We thus developed a convergent synthetic approach to 3 based on Wittig-Horner coupling. The total synthesis involved 12 steps with a total yield of 30% (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and ¹¹C‐labelling of (E,E)‐1‐(3′,4′‐dihydroxystyryl)‐4‐(3′‐methoxy‐4′‐hydroxystyryl) benzene for PET imaging of amyloid deposits^†

Wang

Mathis

Huang

et al. 2002

Labelled Comp Radiopharmac

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“…Then KOC(CH 3 ) 3 (1.35 g, 12.0 mmol) was added to the solution and after further 10 min stirring 3.0 mmol of the benzaldimine 4a [18,19], 4b [13], 4c [20], 4d [14], or 4e [13]. After 1 h at 90 • C the reaction was stopped by dropwise addition of 150 mL of H 2 O and 100 mL of 10 % HCl.…”

Section: General Procedures For the Preparation Of The (Ee)-44 -Bis(mentioning

confidence: 99%

Comparison of Alkoxy-substituted 4,4´-Distyrylbiphenyls and the Corresponding 4,4´-Distyrylbenzenes

Meier

Lifka

Oehlhof

2008

Zeitschrift Für Naturforschung B

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Configurationally highly pure (E,E)-4,4 -bis(styryl)biphenyls 2a -e were obtained by Siegrist reactions of 4,4 -dimethylbiphenyl 3 and alkoxy-substituted benzaldimines (4a -e). DSC measurements have indicated different crystalline modifications of these conjugated compounds. The stilbenoid chromophores of 2a -e are compared to the stilbenoid chromophores in the OPV series, which have a similar length of conjugation. The intense fluorescence and the high transparency in the visible region are promising properties for an application of the donor-substituted compounds 2a -e in twophoton absorption (TPA) techniques.

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“…Consequently, the molecules with only one peripheral chain per arm organize in lamellar phases for the latter flexible type of cores due to adequate folding, whereas shape-persistent molecules commonly crystallize [22,35] and only in rare cases exhibit lamellar or columnar mesophases [21,23]. The flexibility of the core scaffold can be monitored when comparing the columnar diameters in the hexagonal phases of stilbenoid structure (2) (4.85 nm (40 C)) [58] and oligobenzoate (1) should be almost identical in size, the columnar diameter differs by 0.6 nm.…”

Section: Columnar Liquid Crystals From Star-shaped Mesogensmentioning

confidence: 99%

Polymorphism in liquid crystals from star-shaped mesogens

Gemming¹,

Popov²,

Lehmann³

2007

Philosophical Magazine Letters

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Star-shaped molecules, based on a phloroglucinol core with three oligobenzoate arms, are powerful mesogens that can be combined to columnar liquid crystalline materials and soft organic crystals. The structural properties of such modern materials exhibit polymorphism at two different length scales. On the molecular level, the mesogens are highly flexible molecules with a large variety of almost isoenergetic conformers of varying propensity towards regular stacking in the bulk phase. On the supramolecular level, polymorphic structures occur, which comprise different liquid crystalline phases with anisotropic columnar order and soft crystals with a more isotropic three-dimensional ordering. For the smallest mesogen, the present results are evidence that the two forms of polymorphism are linked. Columnar liquid crystals are formed from a low-symmetry, folded conformer, which already accounts for the nano-segregation of the planar aromatic centre and the flexible aliphatic chain parts of the mesogen, whereas the soft, more isotropic crystals are grown from the C 3 -symmetric, star-shaped conformer of a derivative with shorter alkyl chains. Molecular dynamics simulations confirm the stability of each structure at room temperature.

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Synthese, Flüssigkristallinität und Photochemie von Di- und Tristyrylbenzolen mit Alkoxyseitenketten / Synthesis, Liquid Crystals and Photochemistry of Di- and Tristyrylbenzenes with Alkoxy Side Chains

Cited by 38 publications

References 5 publications

Synthesis and ¹¹C‐labelling of (E,E)‐1‐(3′,4′‐dihydroxystyryl)‐4‐(3′‐methoxy‐4′‐hydroxystyryl) benzene for PET imaging of amyloid deposits^†

Synthesis and ¹¹C‐labelling of (E,E)‐1‐(3′,4′‐dihydroxystyryl)‐4‐(3′‐methoxy‐4′‐hydroxystyryl) benzene for PET imaging of amyloid deposits^†

Comparison of Alkoxy-substituted 4,4´-Distyrylbiphenyls and the Corresponding 4,4´-Distyrylbenzenes

Polymorphism in liquid crystals from star-shaped mesogens

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Synthese, Flüssigkristallinität und Photochemie von Di- und Tristyrylbenzolen mit Alkoxyseitenketten / Synthesis, Liquid Crystals and Photochemistry of Di- and Tristyrylbenzenes with Alkoxy Side Chains

Cited by 38 publications

References 5 publications

Synthesis and 11C‐labelling of (E,E)‐1‐(3′,4′‐dihydroxystyryl)‐4‐(3′‐methoxy‐4′‐hydroxystyryl) benzene for PET imaging of amyloid deposits†

Synthesis and 11C‐labelling of (E,E)‐1‐(3′,4′‐dihydroxystyryl)‐4‐(3′‐methoxy‐4′‐hydroxystyryl) benzene for PET imaging of amyloid deposits†

Comparison of Alkoxy-substituted 4,4´-Distyrylbiphenyls and the Corresponding 4,4´-Distyrylbenzenes

Polymorphism in liquid crystals from star-shaped mesogens

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Synthesis and ¹¹C‐labelling of (E,E)‐1‐(3′,4′‐dihydroxystyryl)‐4‐(3′‐methoxy‐4′‐hydroxystyryl) benzene for PET imaging of amyloid deposits^†

Synthesis and ¹¹C‐labelling of (E,E)‐1‐(3′,4′‐dihydroxystyryl)‐4‐(3′‐methoxy‐4′‐hydroxystyryl) benzene for PET imaging of amyloid deposits^†