Synthesis of Calixarene-Capped Carbosilane Dendrimers

Lambert, Joseph B.; Kang, Seung-Hyun; Ma, Kuangbiao; Liu, Chunqing; Condie, Allison G.

doi:10.1021/jo802714q

Cited by 15 publications

(8 citation statements)

References 34 publications

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“…Recently a variety of functional moieties introducing carbosilane dendritic molecules has been prepared, characterized, and evaluated for the functional properties [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37]. As one of butadiene grafted hybrid dendrimers, M. Gauthier developed a divergent synthetic scheme for the preparation of high branching functionality hybrid polymers from carbosilane dendrimer substrates and polybutadiene side chains [23].…”

Section: Pt Complex-catalyzed Hydrosilylation Of Unsaturated Hydrocarmentioning

confidence: 99%

“…The first-and secondgeneration of anionic metallacarborane-containing metallodendrimers were formed by the hydrosilylation of carbosilane dendrimers functionalized with four or eight vinyl functions, by using Cs[1,1'--SiMeH-3,3'-Co(1,2-C 2 B 9 H 10 ) 2 ]. The approach involves synthesis of two components, one of which has one calixarene (calix-CH 2 CH=CH 2 ), and the other is the allylterminal carbosilane dendrimer [carbosilane(CH 2 CH=CH 2 ) n ] [27]. New type carbosilane dendrimer is prepared with peripheral multiple functionalities capable of being tied to a calix [4]arene unit, which can bind with a metal cation.…”

Section: Pt Complex-catalyzed Hydrosilylation Of Unsaturated Hydrocarmentioning

confidence: 99%

“…Hydrosilylation of G1 with 1a to give G2p with 12 Si-Cl units, then reacted with 12 allylmagnesium bromides to lead to G2 with 12 allyl groups. Dendrimers G3-G5 tipped with allyl groups reacted with n-calix-(CH 2 ) 3 -SiMe 2 -SiMe 2 -H (1c ) to give the corresponding dendritic generations with calix [4]arenas [27]. 3).…”

Section: Pt Complex-catalyzed Hydrosilylation Of Unsaturated Hydrocarmentioning

confidence: 99%

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Si-C Coupling Reaction of Hydrosilane with Activated Organic Compounds: A Facile Synthetic Route to Organosilicon Compounds

Han¹

2011

COC

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Hydrosilane undergoes useful and interesting Si-C coupling reactions with activated organic compounds such as linear and cyclic alkyl chlorides, polychloromethanes, terminal and internal alkenes, and linear and cyclic conjugated dienes to give a variety of organosilicon compounds with Si-Cl units: 1) thermal induced and Pt-catalyzed hydrosilylation reaction with unsaturated organic compounds, 2) organic salt-catalyzed dehydrochlorinative Si-C coupling reaction with alkyl chlorides, 3) double silylation with olefin, and silylene-trapped ring closure reaction with conjugated dienes. In the quaternary phosphonium chloride-catalyzed dehydrochlorinative Si-C coupling reactions of activated organic compounds with HSiCl3, the reaction with relatively activated allyl chloride and benzyl chloride proceeded at 130 °C to give the corresponding coupling products in good to excellent yields, while that of silylalkyl chlorides and primary/secondary alkyl chlorides required high reaction temperatures of 150 °C and 170 °C, respectively and long reaction times. Reaction with olefin at the high temperature of 180 °C gave double silylation product in good yield. Conjugated dienes reacted with 1a at 150 °C to afford 1,1-dichlorosilacyclopent-3-ene. This review is designed to organize the Si-C coupling reactions into categories that illustrate distinct patterns of reactivity. It is hoped that an understanding of such patterns will stimulate the use of Si-C coupling reactions in the synthesis of organosilicon compounds.

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Section: Pt Complex-catalyzed Hydrosilylation Of Unsaturated Hydrocarmentioning

confidence: 99%

Section: Pt Complex-catalyzed Hydrosilylation Of Unsaturated Hydrocarmentioning

confidence: 99%

Section: Pt Complex-catalyzed Hydrosilylation Of Unsaturated Hydrocarmentioning

confidence: 99%

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Si-C Coupling Reaction of Hydrosilane with Activated Organic Compounds: A Facile Synthetic Route to Organosilicon Compounds

Han¹

2011

COC

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“…The literature presents a limited number of publications on the synthesis of multi(thia)calix[4]arene systems [ 28 , 29 ]. Previous studies have used a wide variety of reactions for the preparation of multi(thia)calix[4]arene systems, e.g., O -alkylation [ 30 ], hydrosilylation [ 31 ], amide formation [ 32 , 33 ], and “click” reactions [ 28 , 34 ]. However, there are almost no convenient approaches to the synthesis of multi(thia)calix[4]arenes with different functional groups on the surface in existing examples of multi(thia)calix[4]arene systems.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Water-Soluble Amino Functionalized Multithiacalix[4]arene via Quaternization of Tertiary Amino Groups

et al. 2018

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A convenient approach to the synthesis of multithiacalix[4]arene derivatives containing amino groups and phthalimide fragments by the formation of quaternary ammonium salts is presented. As the initial macrocycle for the synthesis of multithiacalix[4]arenes, a differently substituted p-tert-butylthiacalix[4]arene containing bromoacetamide and three phthalimide fragments was used in a 1,3-alternate conformation. The macrocycle in cone conformation containing the tertiary amino groups was found to be a convenient core for the multithiacalix[4]arene systems. Interaction of the core multithiacalix[4]arene with monobromoacetamide derivatives of p-tert-butylthiacalix[4]arene resulted in formation in high yields of pentakisthiacalix[4]arene containing quaternary ammonium and phthalimide fragments. The removal of phthalimide groups led to the formation of amino multithiacalix[4]arene in a good yield. Based on dynamic light scattering, it was shown that the synthesized amino multithiacalix[4]arene, with pronounced hydrophobic and hydrophilic fragments, formed dendrimer-like nanoparticles in water via direct supramolecular self-assembly.

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“…Recently, the calixarenes and related macrocycles have been receiving increased attention because of their polydentate ability to bind metals, as well as its selectivity and flexibility in binding to various metals [1][2][3]. As shown in the diagram, calixarenes can change not only the R-group, but also the oxygen to ester to accommodate the different oxidation states of metals.…”

Section: Introductionmentioning

confidence: 99%

Ab Initio Investigating the Bonding and Electronic Structure in Bismuth Calixarene Complexes

Zhao¹,

Fan²

2017

dtetr

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ABSTRACT The geometric and electronic structures of calixarene bismuth(III) complexes have been investigated by ab initio method in this study. Three conformations (cone shape conformation with C 2v symmetry, 1,2-alternative conformation with C 2h symmetry and 1,3-alternative conformation) are investigated as possible binding modes between bismuth fragment and calixarene fragment. The optimized geometries are then compared with the recent reported crystal structure. Two bis-muth(III) fragments are needed to bind with calixarene ligand due to the inert-pair effect. Co-crystalized LiCl-DMSO fragment plays a crucial role in stabilizing the bismuth calixarene crystal, where the binding energy ΔH is estimated to be 55.3 kcal/mol or 56.1 kcal/mol with zero-point energy correction. The estimated ΔG is -28.2 kcal/mol for the complex, which is consistent with the strong HC 4 Bi-ClLi interactions. The trans effect is evidenced by two slight longer Bi-O bond lengths.

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Synthesis of Calixarene-Capped Carbosilane Dendrimers

Cited by 15 publications

References 34 publications

Si-C Coupling Reaction of Hydrosilane with Activated Organic Compounds: A Facile Synthetic Route to Organosilicon Compounds

Si-C Coupling Reaction of Hydrosilane with Activated Organic Compounds: A Facile Synthetic Route to Organosilicon Compounds

Synthesis of Water-Soluble Amino Functionalized Multithiacalix[4]arene via Quaternization of Tertiary Amino Groups

Ab Initio Investigating the Bonding and Electronic Structure in Bismuth Calixarene Complexes

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