An expedient methodology to synthesize macrocyclic compounds in one step based on the Nicholas reaction is disclosed. The key step features two intermolecular reactions followed by an intramolecular reaction from the starting dicobalt hexacarbonyl-propargylic complex. The macrocycles obtained were modified through [2 + 2 + 2] cycloaddition, generating two new C3-symmetric hexasubstituted benzene structures suitable for molecular recognition purposes.
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http://dx.doi.org/10.1021/ol403428p | DOI Listing |
Angew Chem Int Ed Engl
August 2015
Institut of Organic Chemistry, University of Würzburg, Am Hubland, 97074 Würzburg (Germany).
Hexasubstituted C3 -symmetric benzenes with three oligophenylenevinylene (OPV) arms and three pyridyl or phenyl substituents are shape-persistent star mesogens that are sterically crowded in the center. Such molecular structures possess large void spaces between their arms, which have to be filled in condensed phases. For the neat materials, this is accomplished by an exceptional formation of dimers and short-range helical packing in columnar mesophases.
View Article and Find Full Text PDFOrg Lett
January 2014
Instituto de Productos Naturales y Agrobiología , Consejo Superior de Investigaciones Científicas (CSIC), Avda. Francisco Sánchez 3, 38206 La Laguna, Tenerife, Spain.
An expedient methodology to synthesize macrocyclic compounds in one step based on the Nicholas reaction is disclosed. The key step features two intermolecular reactions followed by an intramolecular reaction from the starting dicobalt hexacarbonyl-propargylic complex. The macrocycles obtained were modified through [2 + 2 + 2] cycloaddition, generating two new C3-symmetric hexasubstituted benzene structures suitable for molecular recognition purposes.
View Article and Find Full Text PDFJ Am Chem Soc
April 2008
Laboratoire de Synthèse Supramoléculaire, Département de Chimie, Institut de Pharmacologie, Université de Sherbrooke, 3001, 12e avenue nord, Sherbrooke Québec J1H 5N4, Canada.
A novel very simple C3-symmetric lactam has been rationally designed to self-assemble as dimers or larger platonic solid capsules. Its core flat benzene ring bears three seven-membered lactams, resulting in tripod molecules that aggregate into robust tetrameric capsules. The self-assembly process was templated by tetraethylammonium cations and proven to be reversible by ESI spectroscopy in various solvents.
View Article and Find Full Text PDFChemistry
May 2002
Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, TX 78712-1167, USA.
The conversion of 1,3,5-substituted benzene and mesitylene by electrophilic aromatic substitution and Sonogashira cross-coupling, respectively, furnished the C3-symmetric, hexasubstituted benzene derivatives 1 and 2 with an alternating substitution pattern. Based on the molecular scaffolds obtained, the two systems serve as model compounds for novel receptor molecules with distinct geometric features. X-ray structures have been obtained for 1 and 2, which are discussed in regard to their aptitude as receptor platforms or supramolecular building blocks.
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