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Synthesis and Functionalization of Heteroatom-Bridged Bicyclocalixaromatics, Large Molecular Triangular Prisms with Electron-Rich and -Deficient Aromatic Interiors
Naseer, Muhammad Moazzam1; Wang, De-Xian1; Zhao, Liang2; Huang, Zhi-Tang1; Wang, Mei-Xiang1,2
2011-03-18
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
Volume76Issue:6Pages:1804-1813
AbstractThe synthesis and functionalization of oxygen and nitrogen atom bridged bicyclocalixaromatics of triangular prism structures are reported. By means of a fragment coupling approach, molecular triangular prisms of electron-rich and electron-deficient aromatic interiors were prepared using 1,3 5-tri(p-hydroxyphenyl)benzene and 2,4,6-tri(p-aminophenyl)triazine as base units and chlorotriazines as pillars. Aromatic nucleophilic substitution reaction of chlorotriazine moieties with functionalized amines led to triangular prisms with functionalizations on the peripheral edge positions, while functionalized triangular prisms on the vertex nitrogen positions were obtained using 2,4,6-tri[(p-allylamino)phenyl]triazine derivative as a starting material. Symmetrical and distorted molecular triangular prisms in the solid state were revealed by X-ray crystallography. As evidenced by NMR spectroscopic data, however, all cage molecules synthesized most probably adopted highly symmetric triangular prism structures in solution phase. The functionalized shape-persistent triangular prism structures might find applications in molecular recognition and in the construction of higher and more sophisticated molecular architectures in supramolecular chemistry.
DOI10.1021/jo102483x
Indexed BySCI ; IC
Language英语
WOS IDWOS:000288142800033
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:41[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/72798
Collection中国科学院化学研究所
Corresponding AuthorWang, Mei-Xiang
Affiliation1.Chinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China
2.Tsinghua Univ, Dept Chem, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Minist Educ, Beijing 100084, Peoples R China
Recommended Citation
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Naseer, Muhammad Moazzam,Wang, De-Xian,Zhao, Liang,et al. Synthesis and Functionalization of Heteroatom-Bridged Bicyclocalixaromatics, Large Molecular Triangular Prisms with Electron-Rich and -Deficient Aromatic Interiors[J]. JOURNAL OF ORGANIC CHEMISTRY,2011,76(6):1804-1813.
APA Naseer, Muhammad Moazzam,Wang, De-Xian,Zhao, Liang,Huang, Zhi-Tang,&Wang, Mei-Xiang.(2011).Synthesis and Functionalization of Heteroatom-Bridged Bicyclocalixaromatics, Large Molecular Triangular Prisms with Electron-Rich and -Deficient Aromatic Interiors.JOURNAL OF ORGANIC CHEMISTRY,76(6),1804-1813.
MLA Naseer, Muhammad Moazzam,et al."Synthesis and Functionalization of Heteroatom-Bridged Bicyclocalixaromatics, Large Molecular Triangular Prisms with Electron-Rich and -Deficient Aromatic Interiors".JOURNAL OF ORGANIC CHEMISTRY 76.6(2011):1804-1813.
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