Synthesis of 1-amino-12-hydroxyl-perylene tetra-(alkoxycarbonyl) for selective sensing of fluoride

Ran Wang; Jiaofu Li; Gang Li; Chong Hao; Yunxin Zhang; Shuaihua Wang; Jianfeng Zhao; Qingyun Liu; Zhiqiang Shi

doi:10.1016/j.dyepig.2018.04.012

Synthesis of 1-amino-12-hydroxyl-perylene tetra-(alkoxycarbonyl) for selective sensing of fluoride

Ran Wang, Jiaofu Li, Gang Li, Chong Hao, Yunxin Zhang, Shuaihua Wang, Jianfeng Zhao, Qingyun Liu, Zhiqiang Shi

SCHOOL OF FLEXIBLE ELECTRONICS(FUTURE TECHNOLOGIES)|INSTITUTE OF ADVANCED MATERIALS(IAM)

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

13 Scopus citations

Abstract

A perylene tetra-(alkoxycarbonyl) derivative (compound 2) substituted with amino and hydroxyl at the same side was synthesized through an intramolecular rearrangement mechanism. Its chemical structure was fully confirmed by NMR, FT-IR, HRMS spectra and was further confirmed by a cyclic condensation reaction to yield a seven membered heterocycle annulated compound 3. The properties of them were detected by absorption, fluorescence spectra and electrochemical response. Compound 2 was used as colorimetric and fluorescent probe for fluoride ion detection with remarkable selectivity owing to the intermolecular proton transfer (IPT) process between hydroxyl group and the fluoride ion.

Original language	English
Pages (from-to)	225-232
Number of pages	8
Journal	Dyes and Pigments
Volume	156
DOIs	https://doi.org/10.1016/j.dyepig.2018.04.012
State	Published - Sep 2018

Keywords

Fluorescent probe
Fluoride ion
Intermolecular proton transfer
Intramolecular rearrangement
Perylene

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10.1016/j.dyepig.2018.04.012

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title = "Synthesis of 1-amino-12-hydroxyl-perylene tetra-(alkoxycarbonyl) for selective sensing of fluoride",

abstract = "A perylene tetra-(alkoxycarbonyl) derivative (compound 2) substituted with amino and hydroxyl at the same side was synthesized through an intramolecular rearrangement mechanism. Its chemical structure was fully confirmed by NMR, FT-IR, HRMS spectra and was further confirmed by a cyclic condensation reaction to yield a seven membered heterocycle annulated compound 3. The properties of them were detected by absorption, fluorescence spectra and electrochemical response. Compound 2 was used as colorimetric and fluorescent probe for fluoride ion detection with remarkable selectivity owing to the intermolecular proton transfer (IPT) process between hydroxyl group and the fluoride ion.",

keywords = "Fluorescent probe, Fluoride ion, Intermolecular proton transfer, Intramolecular rearrangement, Perylene",

author = "Ran Wang and Jiaofu Li and Gang Li and Chong Hao and Yunxin Zhang and Shuaihua Wang and Jianfeng Zhao and Qingyun Liu and Zhiqiang Shi",

note = "Publisher Copyright: {\textcopyright} 2018",

year = "2018",

month = sep,

doi = "10.1016/j.dyepig.2018.04.012",

language = "英语",

volume = "156",

pages = "225--232",

journal = "Dyes and Pigments",

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TY - JOUR

T1 - Synthesis of 1-amino-12-hydroxyl-perylene tetra-(alkoxycarbonyl) for selective sensing of fluoride

AU - Wang, Ran

AU - Li, Jiaofu

AU - Li, Gang

AU - Hao, Chong

AU - Zhang, Yunxin

AU - Wang, Shuaihua

AU - Zhao, Jianfeng

AU - Liu, Qingyun

AU - Shi, Zhiqiang

PY - 2018/9

Y1 - 2018/9

N2 - A perylene tetra-(alkoxycarbonyl) derivative (compound 2) substituted with amino and hydroxyl at the same side was synthesized through an intramolecular rearrangement mechanism. Its chemical structure was fully confirmed by NMR, FT-IR, HRMS spectra and was further confirmed by a cyclic condensation reaction to yield a seven membered heterocycle annulated compound 3. The properties of them were detected by absorption, fluorescence spectra and electrochemical response. Compound 2 was used as colorimetric and fluorescent probe for fluoride ion detection with remarkable selectivity owing to the intermolecular proton transfer (IPT) process between hydroxyl group and the fluoride ion.

AB - A perylene tetra-(alkoxycarbonyl) derivative (compound 2) substituted with amino and hydroxyl at the same side was synthesized through an intramolecular rearrangement mechanism. Its chemical structure was fully confirmed by NMR, FT-IR, HRMS spectra and was further confirmed by a cyclic condensation reaction to yield a seven membered heterocycle annulated compound 3. The properties of them were detected by absorption, fluorescence spectra and electrochemical response. Compound 2 was used as colorimetric and fluorescent probe for fluoride ion detection with remarkable selectivity owing to the intermolecular proton transfer (IPT) process between hydroxyl group and the fluoride ion.

KW - Fluorescent probe

KW - Fluoride ion

KW - Intermolecular proton transfer

KW - Intramolecular rearrangement

KW - Perylene

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U2 - 10.1016/j.dyepig.2018.04.012

DO - 10.1016/j.dyepig.2018.04.012

M3 - 文章

AN - SCOPUS:85045376614

SN - 0143-7208

VL - 156

SP - 225

EP - 232

JO - Dyes and Pigments

JF - Dyes and Pigments

ER -

Synthesis of 1-amino-12-hydroxyl-perylene tetra-(alkoxycarbonyl) for selective sensing of fluoride

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