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

28 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

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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",

note = "The work was supported by a grant from the Research Committee of Hong Kong Baptist University (FRG2/11-12/121).",

year = "2013",

month = sep,

day = "28",

doi = "10.1039/c3ra41456f",

language = "English",

volume = "3",

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journal = "RSC Advances",

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TY - JOUR

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

N1 - The work was supported by a grant from the Research Committee of Hong Kong Baptist University (FRG2/11-12/121).

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.

UR - https://www.scopus.com/pages/publications/84882616347

U2 - 10.1039/c3ra41456f

DO - 10.1039/c3ra41456f

M3 - Journal article

AN - SCOPUS:84882616347

SN - 2046-2069

VL - 3

SP - 15762

EP - 15768

JO - RSC Advances

JF - RSC Advances

IS - 36

ER -

Ratiometric spiropyran-based fluorescent pH probe

Abstract

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