ICCAS OpenIR
Noncovalent Synthesis of Shape-Persistent Cyclic Hexamers from Ditopic Hydrazide-Based Supramolecular Synthons and Asymmetric Induction of Supramolecular Chirality
Yang, Yong; Xue, Min; Xiang, Jun-Feng; Chen, Chuan-Feng
2009-09-09
Source PublicationJOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN0002-7863
Volume131Issue:35Pages:12657-12663
AbstractWith properly encoded recognition sites and a well-defined algorithm for intermolecular and intramolecular interactions, the 120 degrees spacer linked ditopic hydrazide-based supramolecular synthons were found to self-assemble into shape-persistent cyclic hexamers in apolar solvents. The two hydrazide motifs displayed separate sets of signals in the NMR spectra because of the interlocked conformation. While in hydrogen bonding competitive solvent such as DMSO-d(6) the spectra were in agreement with the structures with C(2) axes Moreover, the terminative groups were found to affect the stability of the assemblies substantially. Consequently, the monomer with ureido-hydrazide terminative groups could form the most stable cyclic hexamer in solution for the attractive spectator secondary electrostatic interactions. Owing to the dynamically and kinetically stable nature of these kinds of assemblies, the assembly from the monomer with chiral auxiliary terminative groups also displayed supramolecular chirality in solution, which was confirmed by concentration-dependent CD spectra.
DOI10.1021/ja9029335
Indexed BySCI ; IC
Language英语
WOS IDWOS:000269735800040
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:29[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/66178
Collection中国科学院化学研究所
Corresponding AuthorChen, Chuan-Feng
AffiliationChinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China
Recommended Citation
GB/T 7714
Yang, Yong,Xue, Min,Xiang, Jun-Feng,et al. Noncovalent Synthesis of Shape-Persistent Cyclic Hexamers from Ditopic Hydrazide-Based Supramolecular Synthons and Asymmetric Induction of Supramolecular Chirality[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2009,131(35):12657-12663.
APA Yang, Yong,Xue, Min,Xiang, Jun-Feng,&Chen, Chuan-Feng.(2009).Noncovalent Synthesis of Shape-Persistent Cyclic Hexamers from Ditopic Hydrazide-Based Supramolecular Synthons and Asymmetric Induction of Supramolecular Chirality.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,131(35),12657-12663.
MLA Yang, Yong,et al."Noncovalent Synthesis of Shape-Persistent Cyclic Hexamers from Ditopic Hydrazide-Based Supramolecular Synthons and Asymmetric Induction of Supramolecular Chirality".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 131.35(2009):12657-12663.
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