Synthesis of 9,9′‐Spirobifluorenes and 4,5‐Diaza‐9,9′‐spirobifluorenes and Their Application as Affinity Materials for Quartz Crystal Microbalances

Stobe, Caroline; Pyka, Isabella; Linke, Alexander; Müller, S.; Schnakenburg, Gregor; Waldvogel, Siegfried R.; Lützen, Arne

doi:10.1002/cplu.201700105

Cited by 5 publications

(1 citation statement)

References 85 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In previous works 4,5-diazafluoren-9-one, which is prepared from 1,10-phenanthroline, was employed as starting material. However, syntheses of substituted 4,5-diazafluorene derivatives involves many steps [7]. Recently we managed to obtain new chiral dipinodiazafluorenone 1 ((1 R ,3 R ,8 R ,10 R )-2,2,9,9-tetramethyl-3,4,7,8,9,10-hexahydro-1 H -1,3:8,10-dimethanocyclopenta [1,2- b :5,4- b ′]diquinolin-12(2 H )-one) in two steps from (+)-pinocarvone oxime [8].…”

Section: Introductionmentioning

confidence: 99%

Chiral C2-Symmetric Diimines with 4,5-Diazafluorene Units

et al. 2019

View full text Add to dashboard Cite

A synthetic approach to a new group of stable chiral C2-symmetric diimines with the 4,5-diazafluorene core has been developed based on condensation of dipinodiazafluorene with aromatic diamines. The chemical structures of new compounds were proven by spectroscopic methods and X-ray crystallography. All the compounds form solvates with organic solvents (chloroform, benzene, 1,4-dioxane) and water. Specific spectral data of the new compounds are explained using calculated data (DFT). Diimines of the pinodiazafluorene series give colored reactions with transition metal ions and can be regarded as prospective polydentate ligands with interesting luminescent and chiroptical properties.

show abstract

Section: Introductionmentioning

confidence: 99%

Chiral C2-Symmetric Diimines with 4,5-Diazafluorene Units

et al. 2019

View full text Add to dashboard Cite

show abstract

Spiro[cyclopenta[2,1‐ b :3,4‐ b′ ]dipyridine‐5,9 ′ ‐fluorene]

Asako,

Ilies

2024

Encyclopedia of Reagents for Organic Synthesis

View full text Add to dashboard Cite

image [171856‐25‐0] C 23 H 14 N 2 (MW 318.38) InChI = 1S/C23H14N2/c1‐3‐9‐17‐15(7‐1)16‐8‐2‐4‐10‐18(16)23(17)19‐11‐5‐13‐24‐21(19)22‐20(23)12‐6‐14‐25‐22/h1‐14H InChIKey = DRXUKNGBCQEAOM‐UHFFFAOYSA‐N (reagent used as a supporting ligand in metal‐catalyzed processes and as a building block for materials science) Alternative Name: 4,5‐diaza‐9,9′‐spirobifluorene, spirobipyridine, SpiroBpy. Physical Data: melting point = 254–255 °C. Solubility: soluble in acetone, toluene, chloroform, dichloromethane. Form Supplied in: colorless crystalline solid. Preparative Methods: 1–3 . Acetic acid (30 mL) and sulfuric acid (1.0 mL) were added to a 100 mL two‐neck flask containing 5‐([1,1′‐biphenyl]‐2‐yl)‐5 H ‐cyclopenta[2,1‐ b :3,4‐ b ′]dipyridin‐5‐ol (2.6 g, 7.6 mmol), prepared by reaction between 5 H ‐cyclopenta[2,1‐ b :3,4‐ b ′]dipyridin‐5‐one and [1,1′‐biphenyl]‐2‐ylmagnesium iodide, and the mixture was stirred at 90 °C for 24 h. After cooling to room temperature, a light yellow solid precipitated, and it was collected by filtration and washed with acetic acid and heptane. It was neutralized with NaOH (aq.) and extracted with CH 2 Cl 2 three times. The combined organic solution was dried over MgSO 4 , filtered, and concentrated by rotary evaporation. The resulting solid was passed through a pad of silica gel (CH 2 Cl 2 /ethyl acetate = 1:1) to afford spiro[cyclopenta[2,1‐ b :3,4‐ b ′]dipyridine‐5,9′‐fluorene] (2.1 g, 6.6 mmol, 86%) as a colorless solid. It can be further purified by recrystallization from CHCl 3 /Et 2 O/pentane to afford a colorless crystalline solid. Handling, Storage, and Precautions: store in cool, dry, and well‐ventilated area. Toxic if swallowed and in contact with skin.

show abstract

Microporous Triptycene‐Based Affinity Materials on Quartz Crystal Microbalances for Tracing of Illicit Compounds

et al. 2019

Self Cite

View full text Add to dashboard Cite

Triptycene‐based organic molecules of intrinsic microporosity (OMIMs) with extended functionalized π‐surfaces are excellent materials for gas sorption and separation. In this study, the affinities of triptycene‐based OMIM affinity materials on 195 MHz high‐fundamental‐frequency quartz crystal microbalances (HFF‐QCMs) for hazardous and illicit compounds such as piperonal and (–)‐norephedrine were determined. Both new and existing porous triptycene‐based affinity materials were investigated, resulting in very high sensitivities and selectivities that could be applied for sensing purposes. Remarkable results were found for safrole – a starting material for illicit compounds such as ecstasy. A systematic approach highlights the effects of different size of π‐surfaces of these affinity materials, allowing a classification of the properties that might be optimal for the design of future OMIM‐based affinity materials.

show abstract

Synthesis of 9,9′‐Spirobifluorenes and 4,5‐Diaza‐9,9′‐spirobifluorenes and Their Application as Affinity Materials for Quartz Crystal Microbalances

Cited by 5 publications

References 85 publications

Chiral C2-Symmetric Diimines with 4,5-Diazafluorene Units

Chiral C2-Symmetric Diimines with 4,5-Diazafluorene Units

Spiro[cyclopenta[2,1‐ b :3,4‐ b′ ]dipyridine‐5,9 ′ ‐fluorene]

Microporous Triptycene‐Based Affinity Materials on Quartz Crystal Microbalances for Tracing of Illicit Compounds

Contact Info

Product

Resources

About