125065-63-6Relevant academic research and scientific papers
The synthesis of diquinone and dihydroquinone derivatives of calix[4]arene and electrochemical characterization on Au(111) surface
Genorio, Bo?tjan
, p. 496 - 508 (2016/10/19)
Several new electroactive diquinone and dihydroquinone derivatives of calix[4]arene bearing anchor functional groups were designed, synthesized and characterized. A method for selective protection of the hydroquinone-OH groups with trimethylsilyl groups (TMS) either on lower-rim or on upper-rim was developed. Four selected molecules - with sulfide anchor groups and carboxylic anchor groups - were adsorbed onto Au(111) single crystal surface using ex-situ and insitu self-assembly methods. Adsorbed molecules were then electrochemically probed with cyclic voltammetry. All adsorbed molecules showed redox response which changed during cycling. After conditioning CVs stabilized and showed two distinct current peaks for all molecules. Synthesized and electrochemically probed molecules are of interest to: Li-ion batteries (as cathode materials and overcharge protection), beyond Li-ion batteries and redox-flow batteries.
Di-ionizable calix[4]arene-1,3-crown-4 ligands in 1,3-alternate, cone, and partial-cone conformations: Synthesis and metal ion extractions
Yang, Yanfei,Cao, Xiaodan,Purkiss, David W.,Cannon, John F.,Bartsch, Richard A.
experimental part, p. 2233 - 2244 (2012/04/10)
Di-ionizable calix[4]arene-1,3-crown-4 compounds locked in 1,3-alternate, cone, and partial-cone conformations are synthesized for evaluation in metal ion separations. The ionizable functions include carboxylic acid and N-(X)sulfonyl carboxamide groups in which the acidity is tuned by variation of the electron-withdrawing ability of X. Similar synthetic routes were employed for preparation of the cone and 1,3-alternate ligand series. A different preparative route utilizing protection and deprotection was required to obtain the partial-cone analogues. Ligand conformations were confirmed by their proton and/or carbon NMR spectra. X-ray diffraction verified an unusual 1,2-alternate conformation in the solid-state for one synthetic intermediate. Effects of ligand conformation and ionizable group variations on competitive solvent extractions of alkali and alkaline earth metal cations from aqueous solutions into chloroform were assessed. Single species solvent extractions of Hg 2+ and Pb2+ were also performed.
Microwave-assisted synthesis of 1,3-dialkyl ethers of calix[4]arenes: Application to the synthesis of cesium selective calix[4]crown-6 ionophores
Nayak, Sandip K.,Choudhary, Manoj K.
supporting information; experimental part, p. 141 - 144 (2012/01/17)
Partial etherification of phenolic-OH groups of calix[4]arenes with various alkyl halides/tosylates and K2CO3 under microwave irradiation afforded 1,3-dialkoxycalix[4]arenes in their cone conformation only as predominant/sole product
Synthesis and metal ion extraction of calix[4]arene mono- and diacids with 2-methoxyethoxy pendant groups
Yang, Yanfei,Lee, Eun Kyung,Zhou, Hui,Surowiec, Kazimierz,Bartsch, Richard A.
scheme or table, p. 197 - 204 (2012/03/27)
A mono-ionizable calix[4]arene-based ligand with three 2-methoxyethoxy pendant groups is synthesized. A di-ionizable analogue with two 2-methoxyethoxy pendant groups is also prepared. Competitive solvent extractions of alkali metal cations and of alkaline
25,26-Dialkoxycalix[4]arenes. Part 1: 25-Alkoxy-26,27-diacetoxy route
Wu, Fung-Ying,Chang, Kai-Fu,Kuo, Cheng-Han,Chen, Kuan-Chih,Lee, Kuo-Chang,Huang, Chiun-Shiang,Chiang, Yung-Sheng,Lin, Lee-Gin
, p. 3238 - 3247 (2011/05/17)
Acetylation of calix[4]arene 1,3-dialkyl ethers yielded the corresponding monoacetates. The 1H NMR spectral analysis indicated that the products' alkoxy moieties were 'rotation restricted'. Acylation of calix[4]arene monoalkyl ethers with acety
Calix[4]arene-dithiacrown ethers: synthesis and potentiometric membrane sensing of Hg2+
Yang, Yanfei,Cao, Xiaodan,Surowiec, Malgorzata,Bartsch, Richard A.
experimental part, p. 447 - 454 (2010/03/03)
A series of calix[4]arene-dithiacrown-5 and -dithiacrown-6 compounds in cone and 1,3-alternate conformations has been synthesized. Responses of these ionophores to Hg2+ and competing metal ions were determined in solvent polymeric membrane electrodes. High potentiometric selectivity for Hg2+ over Na+ and a variety of transition and heavy metal ions was obtained.
Selective etherification of calix[4]arenes
Wang, Wen-Guang,Zheng, Qi-Yu,Huang, Zhi-Tang
, p. 3711 - 3718 (2007/10/03)
Calix[4]arenes 1 or 2 react with alkyl halides and aqueous potassium hydroxide in the presence of PEG as phase transfer catalyst at room temperature to give the selectively distally dietherified product 3 or 4 in excellent yields. While at the same reacti
p-Triallylcalix[4]arene: The final member of the p-allylcalix[4]arenes
Ho, Zong-Chia,Ku, Ming-Chung,Shu, Chun-Mei,Lin, Lee-Gin
, p. 13189 - 13200 (2007/10/03)
The heat-induced Claisen rearrangement of calix[4]arene triallyl ether 6a produced the title compound, p-triallylcalix[4]arene (7). The triallyl ether 6a was prepared from calix[4]arene 1,3-diallyl ether (1a) in a three-step process. Benzoylation of 1,3-diallyl ether 1a, und separate reaction conditions, resulted in the formation of either one of the isomeric pair of monobenzoates 2 or 3a. The allylation of 3a and subsequent debenzoylation yielded calix[4]arene triallyl ether 6a. The synthesis and structural assignment of these calix[4]arene derivatives are discussed. Further study of this four-step conversion for other calix[4]arene trialkyl ether derivatives is also presented.
Selective Functionalization of Calixarenes at the Upper Rim
Loon, Jan-Dirk van,Arduini, Arturo,Coppi, Laura,Verboom, Willem,Pochini, Andrea,et al.
, p. 5639 - 5646 (2007/10/02)
Methods are described for the selective diametrical functionalization of calixarenes at the upper rim, either by the selective removal of the p-tert-butyl groups and subsequent substitution at the free phenol rings or by selective reactions at the phenol rings of dialkoxycalixarenes without the tert-butyl groups.This includes selective mercuration and the synthesis of 5,17-di-tert-butyl-26,28-dimethoxy-11,23-diphenylcalixarene (13), of which the crystal structure is described.The first synthesis of macrocyclic diquinones derived from calixarenes (calixdiquinones) is described.
