Chapter 5.2 Five-membered ring systems: Pyrroles and benzo derivatives

Janosik, Tomasz; Bergman, Jan; Pelkey, Erin T.

doi:10.1016/s0959-6380(05)80048-0

Cited by 5 publications

(1 citation statement)

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“…Spiropyrrolidone-3,3 0 -oxoindole is a major skeleton in a wide range of optically active natural products. [13] Jorgensen et al [14] reported an effective organocatalytic enantioselective and regioselective S N Ar reaction among reactive aryl moiety and 1,3-dicarbonyls (Scheme 1a). The phase transfer catalysis was applied under mild circumstances to give the corresponding spiropyrrolidone-3,3 0 -oxoindole derivatives in high yields.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and self‐assembly of fluorescent fluorine‐containing liquid crystals

Radwan

Makhlouf

2021

Luminescence

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S N Ar has been used to synthesize various functionalized derivatives of pentafluorobenzenes which are highly specific at the para position; and consequently are ideal for building calamitic (rod-like) liquid crystalline molecular systems. Here, we display the effectiveness of S N Ar chemistry as a convenient method toward the synthesis of fluorescent liquid crystalline perfluorinated comprising ethers and thioethers in excellent yields and high purity. In the current work, we describe the synthesis, self-assembly, and mesogenic properties of new perfluorinated para-terphenyls bearing various para-substituted alkoxy and thioalkoxy chains. The terphenyl core was prepared using Cu(I) (or Cu(I)/phenanthroline)-catalyzed decarboxylative carboncarbon (or carbon-oxygen [sulfur]) cross-coupling from the analogous aromatic iodide and fluorobenzoate potassium salt. The molecular structures of the prepared perfluorinated terphenyls were demonstrated with 1 H, 13 C, and 19 F NMR, as well as FT-IR and X-ray crystallography. The liquid crystalline properties and mesogenic phases were characterized with differential scanning calorimetry and high-resolution polarized optical microscope. Both UV-visible absorbance and emission spectra demonstrated solvatochromism. Supramolecular self-assembly of the generated perfluorinated para-terphenyls was monitored by van der Waals and π-π stacking interaction forces. The creation of nanofibrous architectures was monitored by scanning electron microscopy.

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Section: Introductionmentioning

confidence: 99%