Triptycene-Derived Photoresponsive Fluorescent Azo-Polymer as Chemosensor for Picric Acid Detection

Mosim Ansari; Ranajit Bera; Snehasish Mondal; Neeladri Das

doi:10.1021/acsomega.9b00497

Triptycene-Derived Photoresponsive Fluorescent Azo-Polymer as Chemosensor for Picric Acid Detection

Mosim Ansari, Ranajit Bera, Snehasish Mondal, Neeladri Das^*

^*Corresponding author for this work

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

38 Scopus citations

Abstract

Two new triptycene-based azobenzene-functionalized polymers (TBAFPs) have been synthesized using the well-known Pd-catalyzed Sonogashira cross-coupling polycondensation reaction between 2,6-diethynyltriptycene and (meta or para) dibromo-azobenzenes. Enhancement of the fluorescent emission intensity was observed upon trans → cis isomerization of -N-N- linkage in TBAFPs. The cis-lifetime of TBAFP1 is rather long (greater than 2 days). The resulting materials were tested as a potential chemosensor for the detection of picric acid (PA) - a water pollutant as well as chemical constituent of explosives used in warfare. PA was found to interact strongly with TBAFPs, which led to significant quenching of the latter's fluorescence emission intensities. The binding constants are in the order of 10⁵ M^-1. TBAFPs were also able to detect PA in nanomolar concentrations.

Original language	English
Pages (from-to)	9383-9392
Number of pages	10
Journal	ACS Omega
Volume	4
Issue number	5
DOIs	https://doi.org/10.1021/acsomega.9b00497
State	Published - 29 May 2019
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2019 American Chemical Society.

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering

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10.1021/acsomega.9b00497

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title = "Triptycene-Derived Photoresponsive Fluorescent Azo-Polymer as Chemosensor for Picric Acid Detection",

abstract = "Two new triptycene-based azobenzene-functionalized polymers (TBAFPs) have been synthesized using the well-known Pd-catalyzed Sonogashira cross-coupling polycondensation reaction between 2,6-diethynyltriptycene and (meta or para) dibromo-azobenzenes. Enhancement of the fluorescent emission intensity was observed upon trans → cis isomerization of -N-N- linkage in TBAFPs. The cis-lifetime of TBAFP1 is rather long (greater than 2 days). The resulting materials were tested as a potential chemosensor for the detection of picric acid (PA) - a water pollutant as well as chemical constituent of explosives used in warfare. PA was found to interact strongly with TBAFPs, which led to significant quenching of the latter's fluorescence emission intensities. The binding constants are in the order of 105 M-1. TBAFPs were also able to detect PA in nanomolar concentrations.",

author = "Mosim Ansari and Ranajit Bera and Snehasish Mondal and Neeladri Das",

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AU - Bera, Ranajit

AU - Mondal, Snehasish

AU - Das, Neeladri

PY - 2019/5/29

Y1 - 2019/5/29

N2 - Two new triptycene-based azobenzene-functionalized polymers (TBAFPs) have been synthesized using the well-known Pd-catalyzed Sonogashira cross-coupling polycondensation reaction between 2,6-diethynyltriptycene and (meta or para) dibromo-azobenzenes. Enhancement of the fluorescent emission intensity was observed upon trans → cis isomerization of -N-N- linkage in TBAFPs. The cis-lifetime of TBAFP1 is rather long (greater than 2 days). The resulting materials were tested as a potential chemosensor for the detection of picric acid (PA) - a water pollutant as well as chemical constituent of explosives used in warfare. PA was found to interact strongly with TBAFPs, which led to significant quenching of the latter's fluorescence emission intensities. The binding constants are in the order of 105 M-1. TBAFPs were also able to detect PA in nanomolar concentrations.

AB - Two new triptycene-based azobenzene-functionalized polymers (TBAFPs) have been synthesized using the well-known Pd-catalyzed Sonogashira cross-coupling polycondensation reaction between 2,6-diethynyltriptycene and (meta or para) dibromo-azobenzenes. Enhancement of the fluorescent emission intensity was observed upon trans → cis isomerization of -N-N- linkage in TBAFPs. The cis-lifetime of TBAFP1 is rather long (greater than 2 days). The resulting materials were tested as a potential chemosensor for the detection of picric acid (PA) - a water pollutant as well as chemical constituent of explosives used in warfare. PA was found to interact strongly with TBAFPs, which led to significant quenching of the latter's fluorescence emission intensities. The binding constants are in the order of 105 M-1. TBAFPs were also able to detect PA in nanomolar concentrations.

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Triptycene-Derived Photoresponsive Fluorescent Azo-Polymer as Chemosensor for Picric Acid Detection

Abstract

Bibliographical note

ASJC Scopus subject areas

UN SDGs

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