Please use this identifier to cite or link to this item: https://doi.org/10.1002/asia.201100409
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dc.titleOne-pot multimolecular macrocyclization for the expedient synthesis of macrocyclic aromatic pentamers by a chain growth mechanism
dc.contributor.authorQin, B.
dc.contributor.authorShen, S.
dc.contributor.authorSun, C.
dc.contributor.authorDu, Z.
dc.contributor.authorZhang, K.
dc.contributor.authorZeng, H.
dc.date.accessioned2014-10-16T08:35:49Z
dc.date.available2014-10-16T08:35:49Z
dc.date.issued2011-12-02
dc.identifier.citationQin, 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
dc.identifier.issn18614728
dc.identifier.urihttp://scholarbank.nus.edu.sg/handle/10635/94421
dc.description.abstractPOCl3-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.
dc.description.urihttp://libproxy1.nus.edu.sg/login?url=http://dx.doi.org/10.1002/asia.201100409
dc.sourceScopus
dc.subjectfoldamers
dc.subjecthydrogen bonds
dc.subjectmacrocycles
dc.subjectmacrocyclization mechanism
dc.subjectsupramolecular chemistry
dc.typeArticle
dc.contributor.departmentCHEMISTRY
dc.description.doi10.1002/asia.201100409
dc.description.sourcetitleChemistry - An Asian Journal
dc.description.volume6
dc.description.issue12
dc.description.page3298-3305
dc.identifier.isiut000297458900017
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