Dinuclear chloride-binding foldamers based on fluorescent oligoureas

Peiju Yang; Jiamin Wang; Chuandong Jia; Xiao Juan Yang; Biao Wu

doi:10.1002/ejoc.201300043

Dinuclear chloride-binding foldamers based on fluorescent oligoureas

Peiju Yang, Jiamin Wang, Chuandong Jia, Xiao Juan Yang, Biao Wu^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

Abstract

A series of dinuclear chloride-binding foldamers - (TEA)₂[L ¹Cl₂]·Et₂O (1), (TEA)₂[L ²Cl₂] (2), (TBA)₂[L³Cl₂] (3), (TBA)₂[L⁴Cl₂] (4), [K(18-crown-6)] ₂[L⁴Cl₂]·H₂O (5), and (TBA)₂[L⁵Cl₂]·H₂O (6) - have been synthesized from naphthyl- and anthracenyl-decorated oligoureas (tetrakisurea to hexakisurea, L¹-L⁵). In the crystal structures of 1-6, the oligoureas adopt helical conformations and two chloride anions are bound inside by the urea groups. The solution binding properties of L¹-L⁵ toward chloride ion were investigated by ¹H NMR and fluorescence spectroscopy. Upon binding of the anions, characteristic downfield shifts of the NH signals and enhanced fluorescent emission relative to the free ligands were observed. In DMSO solution, the ligands each display a 1:1 binding ratio to chloride, with association constants of K = 1.16-7.58 × 10² M^-1, which contrasts with the 1:2 (host to guest) binding mode in the crystal structures. However, the formation of dinuclear foldamers in the less polar solvent CHCl₃ was indicated by the HRMS (ESI) spectra.

Original language	English
Pages (from-to)	3446-3454
Number of pages	9
Journal	European Journal of Organic Chemistry
Issue number	17
DOIs	https://doi.org/10.1002/ejoc.201300043
Publication status	Published - Jun 2013
Externally published	Yes

Keywords

Anion coordination
Anions
Foldamers
Helical structures
Host-guest systems

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10.1002/ejoc.201300043

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Yang, P., Wang, J., Jia, C., Yang, X. J., & Wu, B. (2013). Dinuclear chloride-binding foldamers based on fluorescent oligoureas. European Journal of Organic Chemistry, (17), 3446-3454. https://doi.org/10.1002/ejoc.201300043

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title = "Dinuclear chloride-binding foldamers based on fluorescent oligoureas",

abstract = "A series of dinuclear chloride-binding foldamers - (TEA)2[L 1Cl2]·Et2O (1), (TEA)2[L 2Cl2] (2), (TBA)2[L3Cl2] (3), (TBA)2[L4Cl2] (4), [K(18-crown-6)] 2[L4Cl2]·H2O (5), and (TBA)2[L5Cl2]·H2O (6) - have been synthesized from naphthyl- and anthracenyl-decorated oligoureas (tetrakisurea to hexakisurea, L1-L5). In the crystal structures of 1-6, the oligoureas adopt helical conformations and two chloride anions are bound inside by the urea groups. The solution binding properties of L1-L5 toward chloride ion were investigated by 1H NMR and fluorescence spectroscopy. Upon binding of the anions, characteristic downfield shifts of the NH signals and enhanced fluorescent emission relative to the free ligands were observed. In DMSO solution, the ligands each display a 1:1 binding ratio to chloride, with association constants of K = 1.16-7.58 × 102 M-1, which contrasts with the 1:2 (host to guest) binding mode in the crystal structures. However, the formation of dinuclear foldamers in the less polar solvent CHCl3 was indicated by the HRMS (ESI) spectra.",

keywords = "Anion coordination, Anions, Foldamers, Helical structures, Host-guest systems",

author = "Peiju Yang and Jiamin Wang and Chuandong Jia and Yang, {Xiao Juan} and Biao Wu",

year = "2013",

month = jun,

doi = "10.1002/ejoc.201300043",

language = "English",

pages = "3446--3454",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "17",

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T1 - Dinuclear chloride-binding foldamers based on fluorescent oligoureas

AU - Yang, Peiju

AU - Wang, Jiamin

AU - Jia, Chuandong

AU - Yang, Xiao Juan

AU - Wu, Biao

PY - 2013/6

Y1 - 2013/6

N2 - A series of dinuclear chloride-binding foldamers - (TEA)2[L 1Cl2]·Et2O (1), (TEA)2[L 2Cl2] (2), (TBA)2[L3Cl2] (3), (TBA)2[L4Cl2] (4), [K(18-crown-6)] 2[L4Cl2]·H2O (5), and (TBA)2[L5Cl2]·H2O (6) - have been synthesized from naphthyl- and anthracenyl-decorated oligoureas (tetrakisurea to hexakisurea, L1-L5). In the crystal structures of 1-6, the oligoureas adopt helical conformations and two chloride anions are bound inside by the urea groups. The solution binding properties of L1-L5 toward chloride ion were investigated by 1H NMR and fluorescence spectroscopy. Upon binding of the anions, characteristic downfield shifts of the NH signals and enhanced fluorescent emission relative to the free ligands were observed. In DMSO solution, the ligands each display a 1:1 binding ratio to chloride, with association constants of K = 1.16-7.58 × 102 M-1, which contrasts with the 1:2 (host to guest) binding mode in the crystal structures. However, the formation of dinuclear foldamers in the less polar solvent CHCl3 was indicated by the HRMS (ESI) spectra.

AB - A series of dinuclear chloride-binding foldamers - (TEA)2[L 1Cl2]·Et2O (1), (TEA)2[L 2Cl2] (2), (TBA)2[L3Cl2] (3), (TBA)2[L4Cl2] (4), [K(18-crown-6)] 2[L4Cl2]·H2O (5), and (TBA)2[L5Cl2]·H2O (6) - have been synthesized from naphthyl- and anthracenyl-decorated oligoureas (tetrakisurea to hexakisurea, L1-L5). In the crystal structures of 1-6, the oligoureas adopt helical conformations and two chloride anions are bound inside by the urea groups. The solution binding properties of L1-L5 toward chloride ion were investigated by 1H NMR and fluorescence spectroscopy. Upon binding of the anions, characteristic downfield shifts of the NH signals and enhanced fluorescent emission relative to the free ligands were observed. In DMSO solution, the ligands each display a 1:1 binding ratio to chloride, with association constants of K = 1.16-7.58 × 102 M-1, which contrasts with the 1:2 (host to guest) binding mode in the crystal structures. However, the formation of dinuclear foldamers in the less polar solvent CHCl3 was indicated by the HRMS (ESI) spectra.

KW - Anion coordination

KW - Anions

KW - Foldamers

KW - Helical structures

KW - Host-guest systems

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EP - 3454

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 17

ER -

Dinuclear chloride-binding foldamers based on fluorescent oligoureas

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