Homochiral [2.2]Paracyclophane Self‐Assembly Promoted by Transannular Hydrogen Bonding

Autor:	Khalil A. Abboud, Michael J. Meese, Danielle E. Fagnani, Ronald K. Castellano
Rok vydání:	2016
Předmět:	Stereochemistry Hydrogen bond 010405 organic chemistry Supramolecular chemistry General Chemistry General Medicine Planar chirality 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Intramolecular force Molecule Self-assembly Chirality (chemistry) Cyclophane
Zdroj:	Angewandte Chemie. 128:10884-10889
ISSN:	1521-3757 0044-8249
DOI:	10.1002/ange.201605286
Popis:	[2.2]paracyclophane (pCp), unlike many π-building blocks, has been virtually unexplored in supramolecular constructs. Reported here is the synthesis and characterization of the first pCp derivatives capable of programmed self-assembly into extended cofacial π-stacks in solution and the solid state. The design employs transannular (intramolecular) hydrogen bonds (H-bonds), hitherto unstudied in pCps, between pseudo-ortho-positioned amides of a pCp-4,7,12,15-tetracarboxamide (pCpTA) to preorganize the molecules for intermolecular H-bonding with π-stacked neighbors. X-ray crystallography confirms the formation of homochiral, one-dimensional pCpTA stacks helically laced with two H-bond strands. The chiral sense is dictated by the planar chirality (Rp or Sp ) of the pCpTA monomers. A combination of NMR, IR, and UV/Vis studies confirms the formation of the first supramolecular pCp polymers in solution.
Databáze:	OpenAIRE
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