Synthesis and evaluation of a novel pyrenyl-appended triazole-based thiacalix[4]arene as a fluorescent sensor for Ag+ ion

Xin-Long Ni; Xi Zeng; C Redshaw; Takehiko Yamato

doi:10.1016/j.tet.2011.03.008

Synthesis and evaluation of a novel pyrenyl-appended triazole-based thiacalix[4]arene as a fluorescent sensor for Ag+ ion

Xin-Long Ni, Xi Zeng, C Redshaw, Takehiko Yamato

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Abstract

New fluorescent chemosensors 1,3-alternate-1 and 2 with pyrenyl-appended triazole-based on thiacalix[4]arene were synthesized. The fluorescence spectra changes suggested that chemosensors 1 and 2 are highly selective for Ag⁺ over other metal ions by enhancing the monomer emission of pyrene in neutral solution. However, other heavy metal ions, such as Cu²⁺, and Hg²⁺ quench both the monomer and excimer emission of pyrene acutely. The ¹H NMR results indicated that Ag⁺ can be selectively recognized by the triazole moieties on the receptors 1 and 2 together with the ionophoricity cavity formed by the two inverted benzene rings and sulfur atoms of the thiacalix[4]arene.

Original language	English
Pages (from-to)	3248-3253
Number of pages	6
Journal	Tetrahedron
Volume	67
Issue number	18
DOIs	https://doi.org/10.1016/j.tet.2011.03.008
Publication status	Published - 2011

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10.1016/j.tet.2011.03.008

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title = "Synthesis and evaluation of a novel pyrenyl-appended triazole-based thiacalix[4]arene as a fluorescent sensor for Ag+ ion",

abstract = "New fluorescent chemosensors 1,3-alternate-1 and 2 with pyrenyl-appended triazole-based on thiacalix[4]arene were synthesized. The fluorescence spectra changes suggested that chemosensors 1 and 2 are highly selective for Ag+ over other metal ions by enhancing the monomer emission of pyrene in neutral solution. However, other heavy metal ions, such as Cu2+, and Hg2+ quench both the monomer and excimer emission of pyrene acutely. The 1H NMR results indicated that Ag+ can be selectively recognized by the triazole moieties on the receptors 1 and 2 together with the ionophoricity cavity formed by the two inverted benzene rings and sulfur atoms of the thiacalix[4]arene.",

author = "Xin-Long Ni and Xi Zeng and C Redshaw and Takehiko Yamato",

year = "2011",

doi = "10.1016/j.tet.2011.03.008",

language = "English",

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journal = "Tetrahedron",

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T1 - Synthesis and evaluation of a novel pyrenyl-appended triazole-based thiacalix[4]arene as a fluorescent sensor for Ag+ ion

AU - Ni, Xin-Long

AU - Zeng, Xi

AU - Redshaw, C

AU - Yamato, Takehiko

PY - 2011

Y1 - 2011

N2 - New fluorescent chemosensors 1,3-alternate-1 and 2 with pyrenyl-appended triazole-based on thiacalix[4]arene were synthesized. The fluorescence spectra changes suggested that chemosensors 1 and 2 are highly selective for Ag+ over other metal ions by enhancing the monomer emission of pyrene in neutral solution. However, other heavy metal ions, such as Cu2+, and Hg2+ quench both the monomer and excimer emission of pyrene acutely. The 1H NMR results indicated that Ag+ can be selectively recognized by the triazole moieties on the receptors 1 and 2 together with the ionophoricity cavity formed by the two inverted benzene rings and sulfur atoms of the thiacalix[4]arene.

AB - New fluorescent chemosensors 1,3-alternate-1 and 2 with pyrenyl-appended triazole-based on thiacalix[4]arene were synthesized. The fluorescence spectra changes suggested that chemosensors 1 and 2 are highly selective for Ag+ over other metal ions by enhancing the monomer emission of pyrene in neutral solution. However, other heavy metal ions, such as Cu2+, and Hg2+ quench both the monomer and excimer emission of pyrene acutely. The 1H NMR results indicated that Ag+ can be selectively recognized by the triazole moieties on the receptors 1 and 2 together with the ionophoricity cavity formed by the two inverted benzene rings and sulfur atoms of the thiacalix[4]arene.

U2 - 10.1016/j.tet.2011.03.008

DO - 10.1016/j.tet.2011.03.008

M3 - Article

VL - 67

SP - 3248

EP - 3253

JO - Tetrahedron

JF - Tetrahedron

IS - 18

ER -