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Calix[3]arene-Analogous Metacyclophanes: Synthesis, Structures and Properties with Infinite Potential

Chemical Research Division, Bangladesh Council of Scientific and Industrial Research (BCSIR), Dhanmondi, Dhaka 1205, Bangladesh
Department of Chemistry, Memorial University of Newfoundland, St. John’s, NL A1B 3X7, Canada
Aramco Laboratory for Applied Sensing Research, King Abdullah Institute for Nanotechnology, King Saud University, Riyadh 11451, Saudi Arabia
Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-Machi 1, Saga 840-8502, Japan
Author to whom correspondence should be addressed.
Academic Editors: Mario Berberan-Santos and Paula M. Marcos
Molecules 2020, 25(18), 4202;
Received: 24 August 2020 / Revised: 9 September 2020 / Accepted: 10 September 2020 / Published: 14 September 2020
(This article belongs to the Special Issue Calixarene Complexes: Synthesis, Properties and Applications)
Calixarene-analogous metacyclophanes (CAMs) are a special class of cyclophanes that are cyclic polyaromatic hydrocarbons containing three or more aromatic rings linked by one or more methylene bridging groups. They can be considered to be analogues of calixarenes, since, in both types of molecules, the component aromatic rings are linked by methylene groups, which are meta to each other. Since the prototype or classical calix[4]arene consists of four benzene rings each linked by methylene bridges, which are also meta to each other, it can be considered to be an example of a functionalized []metacyclophane. A metacyclophane (MCP) that consists of three individual hydroxyl-group functionalized aromatic rings linked by methylene groups, e.g., a trihydroxy[1.1.1]MCP may therefore, by analogy, be termed in the broadest sense as a “calix[3]arene” or a “calix[3]arene-analogous metacyclophane”. Most of the CAMs reported have been synthesized by fragment coupling approaches. The design, synthesis and development of functionalized CAMs, MCPs, calixarenes and calixarene analogues has been an area of great activity in the past few decades, due their potential applications as molecular receptors, sensors and ligands for metal binding, and for theoretical studies, etc. In this review article, we focus mainly on the synthesis, structure and conformational properties of [1.1.1]CAMs, i.e., “calix[3]arenes” and their analogues, which contain three functionalized aromatic rings and which provide new scaffolds for further explorations in supramolecular and sensor chemistry. View Full-Text
Keywords: calix[3]arenes; metacyclophanes; calixarene-analogous metacyclophanes; inherent chirality; host-guest chemistry calix[3]arenes; metacyclophanes; calixarene-analogous metacyclophanes; inherent chirality; host-guest chemistry
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Islam, M.M.; Georghiou, P.E.; Rahman, S.; Yamato, T. Calix[3]arene-Analogous Metacyclophanes: Synthesis, Structures and Properties with Infinite Potential. Molecules 2020, 25, 4202.

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