Substituent effects on the reaction of trityl chlorides with Grignard reagents

Oyler, Ryan E.; Ketz, Benjamin E.; Glass, Timothy E.

doi:10.1016/s0040-4039(00)01470-2

Cited by 7 publications

(2 citation statements)

References 8 publications

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“…Trityl alcohol 5 was produced in three steps from ethyl-3-aminobenzoate ( 3 ) in good yield. Chlorination of 5 followed by addition of acetylene Grignard afforded alkyne 6 . Glaser coupling of 6 produced diyne 7 in good yield.…”

Section: Resultsmentioning

confidence: 99%

Cooperative Ratiometric Chemosensors: Pinwheel Receptors with an Integrated Fluorescence System

Raker

Glass

2001

J. Org. Chem.

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The synthesis and fluorescent properties of a second generation cooperative chemical sensor are described. The sensor has two interacting binding pockets for cooperative recognition of two analytes. Cooperative binding activates a ratiometric fluorescent response via formation of an excimer. Binding was characterized by NMR, absorption, and fluorescence spectroscopy. The advantages of separating the recognition elements from the fluorescent response elements are discussed.

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Section: Resultsmentioning

confidence: 99%

Cooperative Ratiometric Chemosensors: Pinwheel Receptors with an Integrated Fluorescence System

Raker

Glass

2001

J. Org. Chem.

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“…To facilitate chromatographic separation, we chose the base stable bulky triphenyl propyne (TPP) group for bay substitution. Standard Sonogashira coupling conditions of 1,6 enriched 1 , 7/1 , 6–3 afforded the isomeric mixture of 1 , 7/1 , 6–5a in 87% combined yield (Scheme )…”

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Syntheses and Properties of 1,6 and 1,7 Perylene Diimides and Tetracarboxylic Dianhydrides

2011

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Via Sonogashira cross-coupling with different alkynes, 1,6 and 1,7 perylene diimides (PDIs) and perylene tetracarboxylic dianhydrides (PTCDs) were synthesized from the corresponding regioisomeric mixture of 1,6/1,7-dibromo precursors. Both bulky triphenyl propyne (TPP) groups and nonbulky hexyl groups allow for facile chromatographic separation. The optical properties of these compounds are discussed. Neutral bay substituents hypsochromically shift both the absorption and emission through deformation from planarity of the perylene core.

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ChemInform Abstract: Substituent Effects on the Reaction of Trityl Chlorides with Grignard Reagents.

Oyler¹,

Ketz²,

Glass³

2001

ChemInform

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Substituent effects on the reaction of trityl chlorides with Grignard reagents

Cited by 7 publications

References 8 publications

Cooperative Ratiometric Chemosensors: Pinwheel Receptors with an Integrated Fluorescence System

Cooperative Ratiometric Chemosensors: Pinwheel Receptors with an Integrated Fluorescence System

Syntheses and Properties of 1,6 and 1,7 Perylene Diimides and Tetracarboxylic Dianhydrides

ChemInform Abstract: Substituent Effects on the Reaction of Trityl Chlorides with Grignard Reagents.

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