Cyclotetrabenzoin: Facile Synthesis of a Shape‐Persistent Molecular Square and Its Assembly into Hydrogen‐Bonded Nanotubes |
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Authors: | Qing Ji Ha T M Le Dr Xiqu Wang Dr Yu‐Sheng Chen Dr Tatyana Makarenko Prof Allan J Jacobson Prof Ognjen Š Miljanić |
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Institution: | 1. Department of Chemistry, University of Houston, 112 Fleming Building, Houston, TX 77204‐5003 (USA);2. Center for Advanced Radiation Source (ChemMatCARS), The University of Chicago, c/o APS/ANL, 9700 South Cass Drive, Argonne, IL 60439 (USA) |
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Abstract: | Cyanide‐catalyzed benzoin condensation of terephthaldehyde produces a cyclic tetramer, which we propose to name cyclotetrabenzoin. Cyclotetrabenzoin is a square‐shaped macrocycle ornamented with four α‐hydroxyketone functionalities pointing away from the central cavity, the dimensions of which are 6.9×6.9 Å. In the solid state, these functional groups extensively hydrogen bond, resulting in a microporous three‐dimensional organic framework with one‐dimensional nanotube channels. This material exhibits permanent—albeit low‐porosity, with a Langmuir surface area of 52 m2 g?1. Cyclotetrabenzoin’s easy and inexpensive synthesis and purification may inspire the creation of other shape‐persistent macrocycles and porous molecular crystals by benzoin condensation. |
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Keywords: | adsorption benzoin condensation dynamic combinatorial chemistry macrocycles shape‐persistent macrocycles |
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