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Cyclotetrabenzoin: Facile Synthesis of a Shape‐Persistent Molecular Square and Its Assembly into Hydrogen‐Bonded Nanotubes
Author(s) -
Ji Qing,
Le Ha T. M.,
Wang Xiqu,
Chen YuSheng,
Makarenko Tatyana,
Jacobson Allan J.,
Miljanić Ognjen Š.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201503851
Subject(s) - tetramer , microporous material , hydrogen bond , condensation , materials science , nanotube , nanotechnology , chemical engineering , crystallography , chemistry , molecule , organic chemistry , composite material , physics , thermodynamics , carbon nanotube , engineering , enzyme
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 m 2 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.