期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 86, 期 19, 页码 13491-13502出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01580
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资金
- Ministry of Science and Technology (Taiwan) [MOST-108-2113-M-002-016-MY3]
- National Taiwan University [NTU-109L883102]
The study demonstrates that 2,6-dimethanolpyridine shows good complementarity towards di(ethylene glycol) for complexation of Na+ ions, enabling efficient synthesis of hetero[2] catenanes, especially in branched systems with multiple isophthalaldehyde units.
In this study we found that 2,6-dimethanolpyridine displays good complementarity toward di(ethylene glycol) for the complexation of Na+ ions, allowing us to use this recognition system for the efficient synthesis of hetero[2] catenanes; indeed, it allowed us to attach multiple copies of [2]catenanes to branched systems presenting multiple isophthalaldehyde units. When we attempted to form a catenane from a preformed macrocycle featuring only a single di(ethylene glycol) unit, reacting it with a di(ethylene glycol) derivative presenting two amino termini, isophthalaldehyde, and templating Na+ ions [i.e., with the aim of using di(ethylene glycol)center dot Na+center dot di(ethylene glycol) recognition to template the formation of the interlocked imino macrocycle], the yields of the hetero[2]catenane and homo[2]catenane, comprising two imino macro- cyclic units, were both poor (14% and 7%, respectively). In contrast, when one or two 2,6-dimethanolpyridine units were present in the preformed macro-cycles, their reactions with the same diamine, dialdehyde, and Na+ ions provided the hetero[2]catenanes with high selectivity and efficiency (44% and 64% yields, respectively), with minimal formation of the competing homo[2]catenane. The high complementary of the 2,6-dimethanolpyridine center dot Na+center dot di(ethylene glycol) ligand pair allowed us to synthesize [2]catenane dimers and trimers directly from corresponding isophthalaldehyde-presenting cores, with yields, after subsequent reduction and methylation, of 42% and 31%, respectively.
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