1,2,3‐Triaminocyclopentadienide Ions — Preparation via an Unusually Rapid Vinylcyclopropene‐Cyclopentadiene Rearrangement

Bartmann, Ekkehard; Mengel, Thomas

doi:10.1002/anie.198402252

Cited by 2 publications

(4 citation statements)

References 9 publications

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“…First, we hypothesized that CHCl 3 generates dichlorocarbene in the presence of DEA by an elimination reaction . Dichlorocarbene, as an active species, undergoes an insertion reaction with N–H and C–H. , Then substitution of DEA with chlorine, elimination of HCl, and the rearrangement reaction all happen simultaneously to generate cycloenes or alkenes. , Cycloenes or alkenes continue to react with dichlorocarbene to generate larger fused rings. , As the carbon condensation proceeds, the cores of C dots are formed and crystallized through heating. The above proposed reaction mechanism is supported by the following experiment results.…”

Section: Resultsmentioning

confidence: 99%

“…46,47 Then substitution of DEA with chlorine, 48 elimination of HCl, and the rearrangement reaction all happen simultaneously to generate cycloenes or alkenes. 49,50 Cycloenes or alkenes continue to react with dichlorocarbene to generate larger fused rings. 51,52 As the carbon condensation proceeds, the cores of C dots are formed and crystallized through heating.…”

Section: Chemistry Of Materialsmentioning

confidence: 99%

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Carbon Dots with Continuously Tunable Full-Color Emission and Their Application in Ratiometric pH Sensing

et al. 2014

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Two types of carbon dots (C dots) exhibiting respective excitation-independent blue emission and excitation-dependent full-color emissions have been synthesized via a mild one-pot process from chloroform and diethylamine. This new bottom-up synthetic strategy leads to highly stable crystalline C dots with tunable surface functionalities in high reproducibility. By detailed characterization and comparison of the two types of C dots, it is proved concretely that the surface functional groups, such as CO and CN, can efficiently introduce new energy levels for electron transitions and result in the continuously adjustable fullcolor emissions. A simplified energy level and electron transition diagram has been proposed to help understand how surface functional groups affect the emission properties. By taking advantage of the unique excitation-dependent full-color emissions, various new applications can be anticipated. Here, as an example, a ratiometric pH sensor using two emission wavelengths of the C dots as independent references has been constructed to improve the reliability and accuracy, and the pH sensor is applied to the measurement of intracellular pH values and cancer diagnosis.

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Section: Resultsmentioning

confidence: 99%

Section: Chemistry Of Materialsmentioning

confidence: 99%

Carbon Dots with Continuously Tunable Full-Color Emission and Their Application in Ratiometric pH Sensing

et al. 2014

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“…Tris(dialkylamino)cyclopropenylium perchlorate reacted with 2 equiv of vinyllithium in THF at low temperature (−40 °C); then, during warming of the reaction mixture, evolution of ethylene occurred, and there resulted formation of the 1,2,3-tris(dialkylamino)cyclopentadienide ion 190 , as observed by NMR …”

Section: Reactions With Nucleophiles With Ring Opening1 Formation Of ...mentioning

confidence: 90%

“…Tris(dialkylamino)cyclopropenylium perchlorate reacted with 2 equiv of vinyllithium in THF at low temperature (-40 °C); then, during warming of the reaction mixture, evolution of ethylene occurred, and there resulted formation of the 1,2,3-tris(dialkylamino)cyclopentadienide ion 190, as observed by NMR. 171 Upon acidification of the reaction solution, 190 was doubly protonated to give cyclic 1,2,3-tris(dialkylamino)vinamidinium perchlorates 191 in 60-70% yields (eq 109).…”

Section: Formation Of Five-membered Ringsmentioning

confidence: 99%