Please use this identifier to cite or link to this item: https://doi.org/10.1002/asia.201100409
Title: One-pot multimolecular macrocyclization for the expedient synthesis of macrocyclic aromatic pentamers by a chain growth mechanism
Authors: Qin, B.
Shen, S.
Sun, C.
Du, Z.
Zhang, K.
Zeng, H. 
Keywords: foldamers
hydrogen bonds
macrocycles
macrocyclization mechanism
supramolecular chemistry
Issue Date: 2-Dec-2011
Citation: Qin, B., Shen, S., Sun, C., Du, Z., Zhang, K., Zeng, H. (2011-12-02). One-pot multimolecular macrocyclization for the expedient synthesis of macrocyclic aromatic pentamers by a chain growth mechanism. Chemistry - An Asian Journal 6 (12) : 3298-3305. ScholarBank@NUS Repository. https://doi.org/10.1002/asia.201100409
Abstract: POCl3-mediated one-pot macrocyclization allows the highly selective formation of five-residue macrocycles that are rigidified by internally placed intramolecular hydrogen bonds. Mechanistic investigation by using tailored competition experiments and kinetic simulation provides a comprehensive model, supporting a chain-growth mechanism underlying the one-pot formation of aromatic pentamers, whereby the successive addition of a bifunctional monomer unit onto either another monomer or the growing oligomeric backbone is faster than other types of bimolecular condensations involving oligomers longer than monomers. DFT calculations at the B3LYP/6-31G* level reveal the five-residue pentamer to be the most stable with respect to alternative four-, six-, and seven-residue macrocycles. These novel mechanistic insights may become useful in analyzing other macrocyclization, oligomerization, and ploymerization reactions. Adding one by one: POCl3-mediated one-pot macrocyclization allows the highly selective formation of five-residue macrocycles that proceeds by a chain-growth mechanism in which the successive addition of a bifunctional monomer unit onto either another monomer or the growing oligomeric backbone is faster than other types of bimolecular condensations involving oligomers longer than monomers (see scheme). © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Source Title: Chemistry - An Asian Journal
URI: http://scholarbank.nus.edu.sg/handle/10635/94421
ISSN: 18614728
DOI: 10.1002/asia.201100409
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