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Shaping the cavity of calixarene architecture for molecular recognition: synthesis and conformational properties of new azocalix[4]arenes
Institution:1. Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS), Departamento de Química Física, Universidade de Santiago de Compostela, 15782, Santiago de Compostela, Spain;2. LAQV-REQUIMTE, Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade NOVA de Lisboa, 2829-516, Caparica, Portugal;1. Analytical Discipline and Centralized Instrument Facility, CSIR-Central Salt and Marine Chemicals Research Institute, G.B. Marg, Bhavnagar 364002, India;2. Academy of Scientific and Innovative Research (AcSIR), CSIR-CSMCRI, G.B. Marg, Bhavnagar 364002, India;1. Analytical Discipline and Centralized Instrument Facility, CSIR-Central Salt and Marine Chemicals Research Institute, Gijubhai Badheka Marg, Bhavnagar 364002, India;2. Academy of Scientific and Innovative Research-CSMCRI, Gijubhai Badheka Marg, Bhavnagar 364002, India
Abstract:A series of new azocalix4]arenes containing one, two, three, and four free phenolic groups have been synthesized through the reaction of 4-nitro- and 2,4-dinitrophenylhydrazines with flexible calix4]arene diquinones as well as through diazocoupling reactions of calix4]arenes. Characterization of synthesized compounds by spectroscopic methods and X-ray diffraction revealed that azocalix4]arenes adopt a cone conformation if they contain at least one free phenolic group. Partial cone or 1,3-alternate conformers of azocalix4]arenes result only when they are devoid of free phenolic groups. The results can be utilized to shape calix4]arene architecture for ionic and molecular recognition.
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