Iminocoumarin based fluorophores: Indispensable scaffolds for rapid, selective and sensitive detection of thiophenol

Dnyaneshwar Kand; Prashant Sahebrao Mandal; Avdhoot Datar; Pinaki Talukdar

doi:10.1016/j.dyepig.2014.02.001

Iminocoumarin based fluorophores: Indispensable scaffolds for rapid, selective and sensitive detection of thiophenol

Dnyaneshwar Kand, Prashant Sahebrao Mandal, Avdhoot Datar, Pinaki Talukdar^*

^*Corresponding author for this work

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

Abstract

Off-on fluorescence probes for the detection of thiophenol were designed based on the reaction mechanism to ensure rapid sensing process. 2,4-Dinitrophenylsulfonyl based probes with iminocoumarin fluorophores were validated by theoretical calculations for their off-fluorescence states. Reaction of these probes with thiophenol released strong fluorescent iminocoumarin species with good response times. These results, upon comparing with reported probes, confirmed that higher pK_aH values of the imino nitrogen of iminocoumarins are important for rapid sensing process. Reactivity of these probes was limited to only thiophenol and no reaction was observed with aliphatic thiols. The benzothiazole substituted probe displayed up to 260-fold fluorescence enhancement upon reaction with thiophenol. Sensing of the analyte by the probe was characterized by change in color from red to yellow and with appearance of the green fluorescence. A detection limit up to 6.9 × 10^-9 M was also determined for this probe.

Original language	English
Pages (from-to)	25-31
Number of pages	7
Journal	Dyes and Pigments
Volume	106
DOIs	https://doi.org/10.1016/j.dyepig.2014.02.001
State	Published - Jul 2014
Externally published	Yes

Keywords

Benzothiazole
Fast responsive
Iminocoumarin
Off-on probe
Selectivity
Thiophenol sensing

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10.1016/j.dyepig.2014.02.001

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@article{257bedbb812148e9bff28e424d30ddb5,

title = "Iminocoumarin based fluorophores: Indispensable scaffolds for rapid, selective and sensitive detection of thiophenol",

abstract = "Off-on fluorescence probes for the detection of thiophenol were designed based on the reaction mechanism to ensure rapid sensing process. 2,4-Dinitrophenylsulfonyl based probes with iminocoumarin fluorophores were validated by theoretical calculations for their off-fluorescence states. Reaction of these probes with thiophenol released strong fluorescent iminocoumarin species with good response times. These results, upon comparing with reported probes, confirmed that higher pKaH values of the imino nitrogen of iminocoumarins are important for rapid sensing process. Reactivity of these probes was limited to only thiophenol and no reaction was observed with aliphatic thiols. The benzothiazole substituted probe displayed up to 260-fold fluorescence enhancement upon reaction with thiophenol. Sensing of the analyte by the probe was characterized by change in color from red to yellow and with appearance of the green fluorescence. A detection limit up to 6.9 × 10-9 M was also determined for this probe.",

keywords = "Benzothiazole, Fast responsive, Iminocoumarin, Off-on probe, Selectivity, Thiophenol sensing",

author = "Dnyaneshwar Kand and Mandal, {Prashant Sahebrao} and Avdhoot Datar and Pinaki Talukdar",

note = "Funding Information: P.T. is grateful to the Director, IISER Pune , and DAE (Grant No. 2010/20/37C/6/BRNS/2480 ) for financial supports. We are also thankful to Dr. Anirban Hazra of IISER Pune for his valuable suggestions on theoretical calculations. D.K. thanks CSIR, P.S.M. thanks DAE and A.D. thanks IISER Pune for research fellowships. ",

year = "2014",

month = jul,

doi = "10.1016/j.dyepig.2014.02.001",

language = "אנגלית",

volume = "106",

pages = "25--31",

journal = "Dyes and Pigments",

issn = "0143-7208",

publisher = "Elsevier BV",

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T1 - Iminocoumarin based fluorophores

T2 - Indispensable scaffolds for rapid, selective and sensitive detection of thiophenol

AU - Kand, Dnyaneshwar

AU - Mandal, Prashant Sahebrao

AU - Datar, Avdhoot

AU - Talukdar, Pinaki

N1 - Funding Information: P.T. is grateful to the Director, IISER Pune , and DAE (Grant No. 2010/20/37C/6/BRNS/2480 ) for financial supports. We are also thankful to Dr. Anirban Hazra of IISER Pune for his valuable suggestions on theoretical calculations. D.K. thanks CSIR, P.S.M. thanks DAE and A.D. thanks IISER Pune for research fellowships.

PY - 2014/7

Y1 - 2014/7

N2 - Off-on fluorescence probes for the detection of thiophenol were designed based on the reaction mechanism to ensure rapid sensing process. 2,4-Dinitrophenylsulfonyl based probes with iminocoumarin fluorophores were validated by theoretical calculations for their off-fluorescence states. Reaction of these probes with thiophenol released strong fluorescent iminocoumarin species with good response times. These results, upon comparing with reported probes, confirmed that higher pKaH values of the imino nitrogen of iminocoumarins are important for rapid sensing process. Reactivity of these probes was limited to only thiophenol and no reaction was observed with aliphatic thiols. The benzothiazole substituted probe displayed up to 260-fold fluorescence enhancement upon reaction with thiophenol. Sensing of the analyte by the probe was characterized by change in color from red to yellow and with appearance of the green fluorescence. A detection limit up to 6.9 × 10-9 M was also determined for this probe.

AB - Off-on fluorescence probes for the detection of thiophenol were designed based on the reaction mechanism to ensure rapid sensing process. 2,4-Dinitrophenylsulfonyl based probes with iminocoumarin fluorophores were validated by theoretical calculations for their off-fluorescence states. Reaction of these probes with thiophenol released strong fluorescent iminocoumarin species with good response times. These results, upon comparing with reported probes, confirmed that higher pKaH values of the imino nitrogen of iminocoumarins are important for rapid sensing process. Reactivity of these probes was limited to only thiophenol and no reaction was observed with aliphatic thiols. The benzothiazole substituted probe displayed up to 260-fold fluorescence enhancement upon reaction with thiophenol. Sensing of the analyte by the probe was characterized by change in color from red to yellow and with appearance of the green fluorescence. A detection limit up to 6.9 × 10-9 M was also determined for this probe.

KW - Benzothiazole

KW - Fast responsive

KW - Iminocoumarin

KW - Off-on probe

KW - Selectivity

KW - Thiophenol sensing

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Iminocoumarin based fluorophores: Indispensable scaffolds for rapid, selective and sensitive detection of thiophenol

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Keywords

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