Ratiometric spiropyran-based fluorescent pH probe

Qi Hua You; Li Fan; Wing Hong CHAN; Albert W M LEE; Shaomin Shuang

doi:10.1039/c3ra41456f

Ratiometric spiropyran-based fluorescent pH probe

Qi Hua You, Li Fan, Wing Hong CHAN^*, Albert W M LEE, Shaomin Shuang

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

26 Citations (Scopus)

Abstract

Spiropyran (SP) is an attractive molecular platform for the design of fluorescent OFF-ON probes for the detection of cations and anions operative on a ring-opening/closing mechanism. By incorporating a benzimidazole moiety at the ortho-position of the oxygen atom of the pyran unit, a ratiometric fluorescent probe in the NIR range for the measurement of pH change in aqueous ACN solution was designed and investigated. The ring-opening mechanism and cis-trans interconversion of the probe are also substantiated by ¹H NMR titration. The probe showed a ratiometric change in the pH range from 7.0 to 5.5 and the pK_a of the probe was calculated to be 5.9. The relative intensity ratio (I_{690 nm}/I_{517 nm}) changed from 0.08 to 2.11 with a more than 26-fold enhancement in response to the pH variation.

Original language	English
Pages (from-to)	15762-15768
Number of pages	7
Journal	RSC Advances
Volume	3
Issue number	36
DOIs	https://doi.org/10.1039/c3ra41456f
Publication status	Published - 28 Sept 2013

Scopus Subject Areas

Chemistry(all)
Chemical Engineering(all)

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title = "Ratiometric spiropyran-based fluorescent pH probe",

abstract = "Spiropyran (SP) is an attractive molecular platform for the design of fluorescent OFF-ON probes for the detection of cations and anions operative on a ring-opening/closing mechanism. By incorporating a benzimidazole moiety at the ortho-position of the oxygen atom of the pyran unit, a ratiometric fluorescent probe in the NIR range for the measurement of pH change in aqueous ACN solution was designed and investigated. The ring-opening mechanism and cis-trans interconversion of the probe are also substantiated by 1H NMR titration. The probe showed a ratiometric change in the pH range from 7.0 to 5.5 and the pKa of the probe was calculated to be 5.9. The relative intensity ratio (I690 nm/I517 nm) changed from 0.08 to 2.11 with a more than 26-fold enhancement in response to the pH variation.",

author = "You, {Qi Hua} and Li Fan and CHAN, {Wing Hong} and LEE, {Albert W M} and Shaomin Shuang",

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T1 - Ratiometric spiropyran-based fluorescent pH probe

AU - You, Qi Hua

AU - Fan, Li

AU - CHAN, Wing Hong

AU - LEE, Albert W M

AU - Shuang, Shaomin

PY - 2013/9/28

Y1 - 2013/9/28

N2 - Spiropyran (SP) is an attractive molecular platform for the design of fluorescent OFF-ON probes for the detection of cations and anions operative on a ring-opening/closing mechanism. By incorporating a benzimidazole moiety at the ortho-position of the oxygen atom of the pyran unit, a ratiometric fluorescent probe in the NIR range for the measurement of pH change in aqueous ACN solution was designed and investigated. The ring-opening mechanism and cis-trans interconversion of the probe are also substantiated by 1H NMR titration. The probe showed a ratiometric change in the pH range from 7.0 to 5.5 and the pKa of the probe was calculated to be 5.9. The relative intensity ratio (I690 nm/I517 nm) changed from 0.08 to 2.11 with a more than 26-fold enhancement in response to the pH variation.

AB - Spiropyran (SP) is an attractive molecular platform for the design of fluorescent OFF-ON probes for the detection of cations and anions operative on a ring-opening/closing mechanism. By incorporating a benzimidazole moiety at the ortho-position of the oxygen atom of the pyran unit, a ratiometric fluorescent probe in the NIR range for the measurement of pH change in aqueous ACN solution was designed and investigated. The ring-opening mechanism and cis-trans interconversion of the probe are also substantiated by 1H NMR titration. The probe showed a ratiometric change in the pH range from 7.0 to 5.5 and the pKa of the probe was calculated to be 5.9. The relative intensity ratio (I690 nm/I517 nm) changed from 0.08 to 2.11 with a more than 26-fold enhancement in response to the pH variation.

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U2 - 10.1039/c3ra41456f

DO - 10.1039/c3ra41456f

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EP - 15768

JO - RSC Advances

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ER -

Ratiometric spiropyran-based fluorescent pH probe

Abstract

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