期刊
ISRAEL JOURNAL OF CHEMISTRY
卷 51, 期 5-6, 页码 578-591出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ijch.201100022
关键词
cucurbituril; host-guest systems; reaction mechanisms; step-growth polymerization; x-ray crystallography
资金
- National Science Foundation [CHE-0615049, CHE-0914745]
This article begins by describing the synthesis and recognition properties of the cucurbit[n]uril homologues CB[5], CB[6], CB[7], CB[8], and CB[10]. Subsequently, we describe the state-of-the-art in understanding the mechanism of CB[n] formation. We describe the experiments that establish that glycoluril (1 H) undergoes condensation with formaldehyde by a combination of chain-growth and step-growth polymerization processes. Chain-growth processes deliver methylene bridged glycoluril oligomers 2C-8C as intermediates that may undergo macrocyclization to nor-seco-CB[n] when the oligomer is long enough (5C-8C) and subsequently form CB[n]. Step-growth processes allow oligomers to condense to give longer oligomers connected by a single CH2-bridge that undergo macrocyclization to deliver (+/-)-bis-nor-seco-CB[6] and bis-nor-seco-CB[10]. Lastly, we describe some of the exciting new recognition processes of the newly formed members of the CB[n] family. For example, bis-nor-seco-CB[10] undergoes homotropic allostery during ternary complex formation, (+/-)-bis-nor-seco-CB[6] exhibits moderately diastereoselective recognition processes (d.r. up to 88 : 12) with chiral ammonium ions in water, and norseco-CB[6] functions as an aldehyde reactive CB[n] synthon that can control the folding of alkanediammonium ions into a backfolded conformation in water.
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