ICCAS OpenIR
Synthesis of (NH)(m)(NMe)(4-m)-Bridged Calix[4]pyridines and the Effect of NH Bridge on Structure and Properties
Zhang, En-Xuan1; Wang, De-Xian1; Huang, Zhi-Tang1; Wang, Mei-Xiang1,2
2009-11-20
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
Volume74Issue:22Pages:8595-8603
AbstractThe (NH)(m)(NMe)(4-m)-bridged calix[4]pyridines (m = 1-4) 19-23 were synthesized in excellent yields from deprotection of N-allyl groups of (NAllyl)(m)(NMe)(4-m)-bridged calix[4]pyridine derivatives 8 and 15-18, which were prepared in moderate yields by macrocyclic 2+2 and 1+3 coupling reactions between simple diamino- and dibromo-substituted fragments, In the solid state, (NH)(m)(NMe)(4-m)-bridged calix[4]pyridines adopted different 1,3-alternate conformations due to mainly the formation of varied conjugation systems of bridging NH units with their neighboring pyridines. In solution, all (NH)(m)(NMe)(4-m)-bridged calix[4]pyridines were very fluxional and the rates of interconversion of various conformational structures were very rapid relative to the NMR time scale, While (NH)(4)-bridged calix[4]pyridine 23 formed the strongest conjugation system, (NH)(2)(NMe)(2)-bridged calix[4]pyridine 21 acted as a selective fluorescence probe in the recognition of zinc(II) ion in solution with the dramatic enhancement of fluorescence intensity.
DOI10.1021/jo901609u
Indexed BySCI ; IC
Language英语
WOS IDWOS:000271662500012
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:33[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/66702
Collection中国科学院化学研究所
Corresponding AuthorWang, De-Xian
Affiliation1.Chinese Acad Sci, Beijing Natl Lab Mol Sci, Inst Chem, Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China
2.Tsinghua Univ, Dept Chem, Minist Educ, Kev Lab Bioorgan Phosphorus Chem & Chem Biol, Beijing 100084, Peoples R China
Recommended Citation
GB/T 7714
Zhang, En-Xuan,Wang, De-Xian,Huang, Zhi-Tang,et al. Synthesis of (NH)(m)(NMe)(4-m)-Bridged Calix[4]pyridines and the Effect of NH Bridge on Structure and Properties[J]. JOURNAL OF ORGANIC CHEMISTRY,2009,74(22):8595-8603.
APA Zhang, En-Xuan,Wang, De-Xian,Huang, Zhi-Tang,&Wang, Mei-Xiang.(2009).Synthesis of (NH)(m)(NMe)(4-m)-Bridged Calix[4]pyridines and the Effect of NH Bridge on Structure and Properties.JOURNAL OF ORGANIC CHEMISTRY,74(22),8595-8603.
MLA Zhang, En-Xuan,et al."Synthesis of (NH)(m)(NMe)(4-m)-Bridged Calix[4]pyridines and the Effect of NH Bridge on Structure and Properties".JOURNAL OF ORGANIC CHEMISTRY 74.22(2009):8595-8603.
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