The synthesis and spectral properties of a stimuli-responsive D-π-A charge transfer dye

Sung Hoon Kim; Seon Yeong Gwon; Jin Seok Bae; Young A. Son

doi:10.1016/j.saa.2010.09.027

The synthesis and spectral properties of a stimuli-responsive D-π-A charge transfer dye

Sung Hoon Kim
, Seon Yeong Gwon
, Jin Seok Bae
, Young A. Son

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

14 Scopus citations

Abstract

A new donor-π-acceptor (D-π-A) type isophorone dye was synthesized by the condensation reaction between 2-(3,5,5-trimethylcyclohex-2-enylidene)- malononitrile and indole-3-carboxaldehyde. The chemical structure of the dye was characterized by ¹H NMR, EA and MS. A novel, chromogenic, fluorescent dye based on indol as donor unit and isophorone as acceptor unit displayed marked UV-visible absorption changes and highly selective fluorescence quenching in the presence of fluoride ion. The dye also exhibited sizeable colour changes when used as a pH-induced molecular switch and as a detector for volatile organic compounds. The absorption and fluorescent intensity of the dye can be reversibly selected by protonation/deprotonation of the amine moiety via control of intramolecular charge transfer (ICT), leading to a molecular switch with "on" and "off" states.

Original language	English
Pages (from-to)	234-237
Number of pages	4
Journal	Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Volume	78
Issue number	1
DOIs	https://doi.org/10.1016/j.saa.2010.09.027
State	Published - Jan 2011

Keywords

Absorption changes
D-π-A
Fluorescent receptor
Fluoride ion sensing
pH stimulation
VOC

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10.1016/j.saa.2010.09.027

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title = "The synthesis and spectral properties of a stimuli-responsive D-π-A charge transfer dye",

abstract = "A new donor-π-acceptor (D-π-A) type isophorone dye was synthesized by the condensation reaction between 2-(3,5,5-trimethylcyclohex-2-enylidene)- malononitrile and indole-3-carboxaldehyde. The chemical structure of the dye was characterized by 1H NMR, EA and MS. A novel, chromogenic, fluorescent dye based on indol as donor unit and isophorone as acceptor unit displayed marked UV-visible absorption changes and highly selective fluorescence quenching in the presence of fluoride ion. The dye also exhibited sizeable colour changes when used as a pH-induced molecular switch and as a detector for volatile organic compounds. The absorption and fluorescent intensity of the dye can be reversibly selected by protonation/deprotonation of the amine moiety via control of intramolecular charge transfer (ICT), leading to a molecular switch with {"}on{"} and {"}off{"} states.",

keywords = "Absorption changes, D-π-A, Fluorescent receptor, Fluoride ion sensing, pH stimulation, VOC",

author = "Kim, \{Sung Hoon\} and Gwon, \{Seon Yeong\} and Bae, \{Jin Seok\} and Son, \{Young A.\}",

year = "2011",

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doi = "10.1016/j.saa.2010.09.027",

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volume = "78",

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journal = "Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy",

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AU - Gwon, Seon Yeong

AU - Bae, Jin Seok

AU - Son, Young A.

PY - 2011/1

Y1 - 2011/1

N2 - A new donor-π-acceptor (D-π-A) type isophorone dye was synthesized by the condensation reaction between 2-(3,5,5-trimethylcyclohex-2-enylidene)- malononitrile and indole-3-carboxaldehyde. The chemical structure of the dye was characterized by 1H NMR, EA and MS. A novel, chromogenic, fluorescent dye based on indol as donor unit and isophorone as acceptor unit displayed marked UV-visible absorption changes and highly selective fluorescence quenching in the presence of fluoride ion. The dye also exhibited sizeable colour changes when used as a pH-induced molecular switch and as a detector for volatile organic compounds. The absorption and fluorescent intensity of the dye can be reversibly selected by protonation/deprotonation of the amine moiety via control of intramolecular charge transfer (ICT), leading to a molecular switch with "on" and "off" states.

AB - A new donor-π-acceptor (D-π-A) type isophorone dye was synthesized by the condensation reaction between 2-(3,5,5-trimethylcyclohex-2-enylidene)- malononitrile and indole-3-carboxaldehyde. The chemical structure of the dye was characterized by 1H NMR, EA and MS. A novel, chromogenic, fluorescent dye based on indol as donor unit and isophorone as acceptor unit displayed marked UV-visible absorption changes and highly selective fluorescence quenching in the presence of fluoride ion. The dye also exhibited sizeable colour changes when used as a pH-induced molecular switch and as a detector for volatile organic compounds. The absorption and fluorescent intensity of the dye can be reversibly selected by protonation/deprotonation of the amine moiety via control of intramolecular charge transfer (ICT), leading to a molecular switch with "on" and "off" states.

KW - Absorption changes

KW - D-π-A

KW - Fluorescent receptor

KW - Fluoride ion sensing

KW - pH stimulation

KW - VOC

UR - https://www.scopus.com/pages/publications/78650701987

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DO - 10.1016/j.saa.2010.09.027

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AN - SCOPUS:78650701987

SN - 1386-1425

VL - 78

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JO - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

JF - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy

IS - 1

ER -

The synthesis and spectral properties of a stimuli-responsive D-π-A charge transfer dye

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