Chiral cage molecules generated by regioselective O-alkylation of a doubly-bridged calix[8]arene |
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| Institution: | 1. Clinical Pharmacokinetics Research Laboratory, Department of Biomedical and Pharmaceutical Sciences, University of Rhode Island Kingston, RI, USA;2. Section on Clinical Psychoneuroendocrinology and Neuropsychopharmacology, National Institute on Alcohol Abuse and Alcoholism Division of Intramural Clinical and Biological Research and National Institute on Drug Abuse Intramural Research Program, Bethesda, MD, USA;3. Medication Development Program, National Institute on Drug Abuse Intramural Research Program, Baltimore, MD, USA;4. Center for Alcohol and Addiction Studies, Department of Behavioral and Social Sciences, Brown University, Providence, RI, USA;1. Department of Chemistry, Faculty of Arts and Sciences, Inönü University, 44280, Malatya, Turkey;2. Dokuz Eylül University, Faculty of Sciences, Department of Physics, 35160, Buca, İzmir, Turkey;1. Molecular and Nanoelectronics Research Group (MNRG), Discipline of Electrical Engineering, IIT Indore, Indore, Madhya Pradesh, 453-552, India;2. Department of Electrical Engineering, Institute of Infrastructure Technology Research and Management, Ahmedabad, Gujarat, 380026, India;3. Laser Materials Processing Division, Raja Ramanna Centre for Advanced Technology, Indore, 452013, India;1. Department of Chemistry, Koneru Lakshmaiah Education Foundation, Vaddeswaram, Guntur (Dist), A.P, India;2. GVK Biosciences Private Limited, Medicinal Chemistry Division 28A, IDA, Nacharam, Hyderabad 500076, Telangana, India |
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| Abstract: | A calix8]arene doubly-bridged at the 1,5-phenol units and 3,7-phenol units has a cage structure with D2d symmetry. Regioselective introduction of methyl groups into the residual 2,4,6,8-phenol units affords five different cage compounds: that is, three racemic compounds, one meso compound, and one achiral compound. This paper reports systematic studies on the preparation methods of these new cage compounds and spectroscopic classification of their molecular symmetries. The results indicate that these compounds have a latent potential as a platform for designing chiral cage molecules with an ionophoric inner cavity. |
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