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Complexation of 2,6-helic[6]arene and its derivatives with 1,1 '-dimethyl-4,4 '-bipyridinium salts and protonated 4,4 '-bipyridinium salts: an acid-base controllable complexation
Li, Jing; Shi, Qiang; Han, Ying; Chen, Chuan-Feng
2019-07-26
Source PublicationBEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
ISSN1860-5397
Volume15Pages:1795-1804
Abstract2,6-Helic[6]arene and its derivatives were synthesized, and their complexation with 1,1'-dimethyl-4,4'-bipyridinium and protonated 4,4'-bipyridinium salts were investigated in detail. It was found that the helic[6]arene and its derivatives could all form 1:1 complexes with both 1,1'-dimethy1-4,4'-bipyridinium salts and protonated 4,4'-bipyridinium salts in solution and in the solid state. Especially, the helic[6]arene and its derivatives containing 2-hydroxyethoxy or 2-methoxyethoxy groups exhibited stronger complexation with the guests than the other helic[6]arene derivatives for the additional multiple hydrogen bonding interactions between the hosts and the guests, which were evidenced by H-1 NMR titrations, X-ray crystal structures and DFT calculations. Moreover, it was also found that the association constants (K-a) of the complexes could be significantly enhanced with larger counteranions of the guests and in less polar solvents. Furthermore, the switchable complexation between the helic[6]arene and protonated 4,4'-bipyridinium salt could be efficiently controlled by acids and bases.
DOI10.3762/bjoc.15.173
Indexed BySCI
Language英语
WOS IDWOS:000477941500001
Citation statistics
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/82722
Collection中国科学院化学研究所
AffiliationChinese Acad Sci, Inst Chem, Beijing 100190, Peoples R China
Recommended Citation
GB/T 7714
Li, Jing,Shi, Qiang,Han, Ying,et al. Complexation of 2,6-helic[6]arene and its derivatives with 1,1 '-dimethyl-4,4 '-bipyridinium salts and protonated 4,4 '-bipyridinium salts: an acid-base controllable complexation[J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY,2019,15:1795-1804.
APA Li, Jing,Shi, Qiang,Han, Ying,&Chen, Chuan-Feng.(2019).Complexation of 2,6-helic[6]arene and its derivatives with 1,1 '-dimethyl-4,4 '-bipyridinium salts and protonated 4,4 '-bipyridinium salts: an acid-base controllable complexation.BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY,15,1795-1804.
MLA Li, Jing,et al."Complexation of 2,6-helic[6]arene and its derivatives with 1,1 '-dimethyl-4,4 '-bipyridinium salts and protonated 4,4 '-bipyridinium salts: an acid-base controllable complexation".BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 15(2019):1795-1804.
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