Structure Determination of Unsolvated Potassium, Rubidium, and Cesium Carbazolates

Dinnebiér, Robert E.; Esbak, Hoda; Olbrich, and Falk; Behrens, Ulrich

doi:10.1021/om060927t

Cited by 12 publications

(13 citation statements)

References 29 publications

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“…The synthesis of monomer 2-(4-((9H-carbazole-9-yl)methyl)benzyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)dione (M) was achieved in three steps as shown in Figure 2. The first step involved the reaction of potassium carbazolate with α,α ′ -dibromo-p-xylene to produce 9-(4-(bromomethyl)benzyl)-9H-carbazole (S1) [47], while the second step afforded 3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione (S2) by the reaction of 5-norbornene-2,3-dicarboxylic anhydride with urea [48]. Finally, M was obtained in 48% yield by the reaction of S1 with S2 [49].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Ring-Opening Metathesis Polymerization of a New Norbornene Dicarboximide with a Pendant Carbazole Moiety

Pragliola

Botta

Troiano

et al. 2019

International Journal of Polymer Science

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A new norbornene dicarboximide presenting a pendant carbazole moiety linked by a p-methylene benzyl spacer is synthesized. This carbazole-functionalized monomer is polymerized via ring-opening metathesis polymerization using Grubbs third-generation catalyst. Microstructural analysis of resulting polymers performed by Nuclear Magnetic Resonance (NMR) shows that they are stereoirregular. Wide-angle X-ray diffraction (WAXD) and thermal (DSC) analysis indicate that polymers are also amorphous. With respect to the fluorescence analysis, both solution and film polymer samples exhibit only “normal structured” carbazole fluorescence, while excimer formation by overlap of carbazole groups is not detected.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Ring-Opening Metathesis Polymerization of a New Norbornene Dicarboximide with a Pendant Carbazole Moiety

Pragliola

Botta

Troiano

et al. 2019

International Journal of Polymer Science

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“…In previous literature examples, increasing alkali metal ionic radius tends to favour the adoption of a multi‐hapto binding motif through the five‐membered condensed ring of the carbazolyl ligand 5. 7, 11 The behaviour of the K + ion within dimer 2 appears to be closer to that in the powder X‐ray diffraction structure of the unsolvated caesium carbazolyl complex Cs(NC 12 H 8 ), which in the main displays a combination of η 1 ‐nitrogen and η 6 ‐arene interactions in the solid state 8…”

Section: Resultsmentioning

confidence: 94%

“…[ 5 , 7 , 11 ] The behaviour of the K + ion within dimer 2 appears to be closer to that in the powder X-ray diffraction structure of the unsolvated caesium carbazolyl complex Cs(NC 12 H 8 ), which in the main displays a combination of η 1 -nitrogen and η 6 -arene interactions in the solid state. [ 8 ]…”

Section: Resultsmentioning

confidence: 99%

Tuning Coordination in s‐Block Carbazol‐9‐yl Complexes

Ortu

Moxey

Blake

et al. 2015

Chemistry A European J

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1,3,6,8-Tetra-tert-butylcarbazol-9-yl and 1,8-diaryl-3,6-di(tert-butyl)carbazol-9-yl ligands have been utilized in the synthesis of potassium and magnesium complexes. The potassium complexes (1,3,6,8-tBu4carb)K(THF)4 (1; carb=C12H4N), [(1,8-Xyl2-3,6-tBu2carb)K(THF)]2 (2; Xyl=3,5-Me2C6H3) and (1,8-Mes2-3,6-tBu2carb)K(THF)2 (3; Mes=2,4,6-Me3C6H2) were reacted with MgI2 to give the Hauser bases 1,3,6,8-tBu4carbMgI(THF)2 (4) and 1,8-Ar2-3,6-tBu2carbMgI(THF) (Ar=Xyl 5, Ar=Mes 6). Structural investigations of the potassium and magnesium derivatives highlight significant differences in the coordination motifs, which depend on the nature of the 1- and 8-substituents: 1,8-di(tert-butyl)-substituted ligands gave π-type compounds (1 and 4), in which the carbazolyl ligand acts as a multi-hapto donor, with the metal cations positioned below the coordination plane in a half-sandwich conformation, whereas the use of 1,8-diaryl substituted ligands gave σ-type complexes (2 and 6). Space-filling diagrams and percent buried volume calculations indicated that aryl-substituted carbazolyl ligands offer a steric cleft better suited to stabilization of low-coordinate magnesium complexes.

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“…Carbazol-9-yl ligands featuring sterically demanding substituents Carbazoles are aromatic, heterocyclic compounds which consist of two benzene rings fused opposite each other on a fivemembered pyrrole ring (Fig. 58 Substituted carbazol-9-yl ligands are finding use in transition metal and lanthanide chemistry, affording compounds with potential applications such as fluorescent probes for anion detection 59 and in the catalysis of a range of reactions. This provides a rigid structure which is excellent for the introduction of functionality in particular into the 1 and 8-positions in order to increase the steric bulk around a nitrogen-coordinated element.…”

Section: Group 16 Complexesmentioning

confidence: 99%

Extremely bulky amide ligands in main group chemistry

Kays

2016

Chem. Soc. Rev.

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The search for extremely sterically demanding monodentate amide ligands to access main group complexes in low-coordination numbers and highly reactive bonding modes is an area of intense research interest. The recent development of three classes of sterically demanding, monodentate amide ligands - the m-terphenyl anilides [N(R){C6H3Ar2-2,6}](-) (Ar = aryl, R = H, methyl, silyl), substituted carbazol-9-yl and the extremely bulky amides [N(R)(Ar')](-) (Ar' = 2,6-{C(H)Ph2}-4-R'-C6H2, R = silyl, aryl, silyloxy, R' = alkyl) is facilitating the isolation of stable species with new coordination modes for the main group elements. These compounds are of fundamental importance not only from the investigation of their structure and bonding, but also the investigation of their reactivity highlights the potential for small molecule activation chemistry under mild conditions and applications in catalysis. This review reports on the recent developments for these compounds with emphasis on their synthesis, structure and reactivity.

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Structure Determination of Unsolvated Potassium, Rubidium, and Cesium Carbazolates

Cited by 12 publications

References 29 publications

Synthesis and Ring-Opening Metathesis Polymerization of a New Norbornene Dicarboximide with a Pendant Carbazole Moiety

Synthesis and Ring-Opening Metathesis Polymerization of a New Norbornene Dicarboximide with a Pendant Carbazole Moiety

Tuning Coordination in s‐Block Carbazol‐9‐yl Complexes

Extremely bulky amide ligands in main group chemistry

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