Recent developments in the coordination chemistry of bis(imino)acenaphthene (BIAN) ligands with s- and p-block elements

Hill, Nicholas J.; Vargas‐Baca, Ignacio; Cowley, Alan H.

doi:10.1039/b815079f

Cited by 149 publications

(142 citation statements)

References 132 publications

(102 reference statements)

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“…Switching from [(dppbian)MgA C H T U N G T R E N N U N G (thf) 3 ] to [(dpp-bian)Ga-GaA C H T U N G T R E N N U N G (dpp-bian)] (1) the pathway for reaction with phenylacetylene changes from acid-base interaction (Scheme 1) to 1,3-dipolar cycloadditions. [9] From a structural point of view, digallene 1 illustrates the influence of the conformational rigidity and electronic lability of the ligand on the molecular structure and chemical properties of the complex.…”

Section: Introductionmentioning

confidence: 99%

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Addition of Alkynes to a Gallium Bis‐Amido Complex: Imitation of Transition‐Metal‐Based Catalytic Systems

Fedushkin¹,

Nikipelov²,

Morozov³

et al. 2011

Chemistry A European J

100

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Acetylene, phenylacetylene, and alkylbutynoates add reversibly to (dpp-bian)Ga-Ga(dpp-bian) (dpp-bian=1,2-bis[(2,6-diisopropylphenyl)-imino]acenaphthene) to give addition products [dpp-bian(R(1)C=CR(2))]Ga-Ga[(R(2)C=CR(1))dpp-bian]. The alkyne adds across the Ga-N-C section, which results in new carbon-carbon and carbon-gallium bonds. The adducts were characterized by electron absorption, IR, and (1)H NMR spectroscopy and their molecular structures have been determined by single-crystal X-ray analysis. According to the X-ray data, a change in the coordination number of gallium from three [in (dpp-bian)Ga-Ga(dpp-bian)] to four (in the adducts) results in elongation of the metal-metal bond by approximately 0.13 Å. The adducts undergo a facile alkynes elimination at elevated temperatures. The equilibrium between [dpp-bian(PhC=CH)]Ga-Ga[(HC=CPh)dpp-bian] and [(dpp-bian)Ga-Ga(dpp-bian) + 2 PhC≡CH] in toluene solution was studied by (1)H NMR spectroscopy. The equilibrium constants at various temperatures (298≤T≤323 K) were determined, from which the thermodynamic parameters for the phenylacetylene elimination were calculated (ΔG°=2.4 kJ mol(-1), ΔH°=46.0 kJ mol(-1), ΔS°=146.0 J K(-1) mol(-1)). The reactivity of (dpp-bian)Ga-Ga(dpp-bian) towards alkynes permits use as a catalyst for carbon-nitrogen and carbon-carbon bond-forming reactions. The bisgallium complex was found to be a highly effective catalyst for the hydroamination of phenylacetylene with anilines. For instance, with [(dpp-bian)Ga-Ga(dpp-bian)] (2 mol%) in benzene more than 99% conversion of PhNH(2) and PhC≡CH into PhN=C(Ph)CH(3) was achieved in 16 h at 90 °C. Under similar conditions, the reaction of 1-aminoanthracene with PhC≡CH catalyzed by (dpp-bian)Ga-Ga(dpp-bian) formed a carbon-carbon bond to afford 1-amino-2-(1-phenylvinyl)anthracene in 99% yield.

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Section: Introductionmentioning

confidence: 99%

“…[1][2][3] Their transition-metal complexes were first reported by Elsevier and van Asselt in the early 1990s.…”

Section: Introductionmentioning

confidence: 99%

Addition of Alkynes to a Gallium Bis‐Amido Complex: Imitation of Transition‐Metal‐Based Catalytic Systems

Fedushkin¹,

Nikipelov²,

Morozov³

et al. 2011

Chemistry A European J

100

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“…41 Furthermore, the ease of preparation of BIAN complexes allows for the incorporation of a wide variety of Schiff bases. 46 Accordingly, we became interested in incorporating the BIAN motif into a known electrocatalytic system. Overall, cobaloximes exhibit three attributes that render them desirable for a study of a BIAN appendage, namely: (i) the capability for electrocatalytic activity, (ii) suitable axial binding sites for the substrates, and (iii) a ligand framework that is compatible with BIAN derivatization.…”

Section: Introductionmentioning

confidence: 99%

Structural and electronic characterization of multi-electron reduced naphthalene (BIAN) cobaloximes

2015

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“…12 Interestingly, there are only a few instances in which BIAN ligands have been used for photoluminescent applications. [13][14][15][16] However, in a recently published study from our laboratory, it was reported that the BIAN ligand can be used as a support for AIE materials.…”

Section: Introductionmentioning

confidence: 99%

Photophysical tuning of the aggregation-induced emission of a series of para-substituted aryl bis(imino)acenaphthene zinc complexes

et al. 2015

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Bis(imino)acenaphthene (BIAN) zinc complexes with para-substituted aryl groups have been synthesized and investigated from the standpoint of their photophysical properties. Each complex was found to be nonemissive in solution. However, complexes 1-6 turned out to be emissive in the solid state, while complexes 7 and 8 remained nonemissive. The emissions for complexes 1-8 displayed color tunability ranging from red-yellow. A detailed crystallographic study of the "as-synthesized" structures revealed a distinct difference in the crystal packing environments of the emissive and nonemissive complexes. Furthermore, a solvatomorphic study provided further emission tunability via changes in the crystal packing environments of each solvatomorph. Lastly, TD-DFT calculations were performed in order to investigate the effect of different para-substituents on the flanking aryl rings of the BIAN ligand.

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Recent developments in the coordination chemistry of bis(imino)acenaphthene (BIAN) ligands with s- and p-block elements

Cited by 149 publications

References 132 publications

Addition of Alkynes to a Gallium Bis‐Amido Complex: Imitation of Transition‐Metal‐Based Catalytic Systems

Addition of Alkynes to a Gallium Bis‐Amido Complex: Imitation of Transition‐Metal‐Based Catalytic Systems

Structural and electronic characterization of multi-electron reduced naphthalene (BIAN) cobaloximes

Photophysical tuning of the aggregation-induced emission of a series of para-substituted aryl bis(imino)acenaphthene zinc complexes

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