Complex interactions of pillar[5]arene with paraquats and bis(pyridinium) derivatives
Li, Chunju1,2; Xu, Qianqian1; Li, Jian1; Yao, Feina1; Jia, Xueshun1,3
AbstractThe complexation behavior of a series of paraquats (G1 center dot 2PF(6)-G5 center dot 2PF(6)) and bis(pyridinium) derivatives (G6 center dot 2PF(6)-G14 center dot 2PF(6)) with pillar[5] arene (P5A) host has been comprehensively investigated by (1)H NMR, ESI mass and UV-vis absorption spectroscopy. It is found that P5A forms 2 : 1 external complexes with N,N'-dialkyl-4,4'-bipyridiniums (G1-G4 center dot 2PF(6)); while it forms 1 : 1 pseudorotaxane-type inclusion complexes with methylene [-(CH(2))(n)-] linked bis(pyridinium) derivatives possessing appropriate chain lengths (n = 3-6, G7-G10 center dot 2PF(6)). Host-guest association constants in dimethyl sulfoxide (DMSO) were determined, indicating G7-G10 center dot 2PF(6) axles form stable [2]pseudorotaxanes with P5A wheel in this very high polarity solvent and 1,4-bis(pyridinium) butane (G8 center dot 2PF(6)) was the most suitable axle unit. Meanwhile, the nature of the substituents attached to 1,4-bis(pyridinium) butane dramatically affects the molecular recognition behavior. The introduction of pyridyls (G13 center dot 2PF(6)) increases not only the K(a) value (4.5 x 10(2) -> 7.4 x 10(2) M(-1)), but also the charge transfer (CT) absorption (colorless -> yellow). Furthermore, the solvent effects have also been investigated, showing they significantly influence the association strength during the course of host-guest complexation. Particularly, the K(a) value of P5A-G13 center dot 2PF(6) in 1 : 1 (v: v) acetone-d(6)/DMSO-d(6) is enhanced by a factor of 7.3 compared with pure DMSO-d(6) (7.4 x 10(2) -> 5.4 x 10(3) M(-1)).
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WOS IDWOS:000275947900011
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Cited Times:218[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Corresponding AuthorLi, Chunju
Affiliation1.Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China
2.Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
3.Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China
Recommended Citation
GB/T 7714
Li, Chunju,Xu, Qianqian,Li, Jian,et al. Complex interactions of pillar[5]arene with paraquats and bis(pyridinium) derivatives[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2010,8(7):1568-1576.
APA Li, Chunju,Xu, Qianqian,Li, Jian,Yao, Feina,&Jia, Xueshun.(2010).Complex interactions of pillar[5]arene with paraquats and bis(pyridinium) derivatives.ORGANIC & BIOMOLECULAR CHEMISTRY,8(7),1568-1576.
MLA Li, Chunju,et al."Complex interactions of pillar[5]arene with paraquats and bis(pyridinium) derivatives".ORGANIC & BIOMOLECULAR CHEMISTRY 8.7(2010):1568-1576.
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