Ratiometric pH responsive fluorescent probes operative on ESIPT

Yim Pan Chan; Li Fan; Qihua You; Wing Hong Chan; Albert W.M. Lee; Shaomin Shuang

doi:10.1016/j.tet.2013.05.023

Ratiometric pH responsive fluorescent probes operative on ESIPT

Yim Pan Chan
, Li Fan
, Qihua You
, 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

38 Citations (Scopus)

Abstract

A series of C-8′-oxime-appended spirobenzopyrans 4a-4d were synthesized and developed as fluorescent pH ratiometric probes operative in HEPES/ACN (8:2, v/v) buffer solutions. Acidochromic conversion of spirobenzopyran to merocyanine open form can facilitate the subsequent enol-keto tautomerization giving dual emissive peaks via the excited state intramolecular proton transfer (ESIPT) mechanism. The pH titrations of 4a show a 68-fold increase in ratiometric intensities ratio (I_{645 nm}/I _{522 nm}) when the pH was switched from 8.0 to 4.0 with a pK _a value of 5.90.

Original language	English
Pages (from-to)	5874-5879
Number of pages	6
Journal	Tetrahedron
Volume	69
Issue number	29
DOIs	https://doi.org/10.1016/j.tet.2013.05.023
Publication status	Published - 22 Jul 2013

User-Defined Keywords

ESIPT
pH sensing
Ratiometric fluorescent probe
Spirobenzopyran

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10.1016/j.tet.2013.05.023

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@article{386189689d39472c8fd099bf9d9e2008,

title = "Ratiometric pH responsive fluorescent probes operative on ESIPT",

abstract = "A series of C-8′-oxime-appended spirobenzopyrans 4a-4d were synthesized and developed as fluorescent pH ratiometric probes operative in HEPES/ACN (8:2, v/v) buffer solutions. Acidochromic conversion of spirobenzopyran to merocyanine open form can facilitate the subsequent enol-keto tautomerization giving dual emissive peaks via the excited state intramolecular proton transfer (ESIPT) mechanism. The pH titrations of 4a show a 68-fold increase in ratiometric intensities ratio (I645 nm/I 522 nm) when the pH was switched from 8.0 to 4.0 with a pK a value of 5.90.",

keywords = "ESIPT, pH sensing, Ratiometric fluorescent probe, Spirobenzopyran",

author = "Chan, \{Yim Pan\} and Li Fan and Qihua You and Chan, \{Wing Hong\} and Lee, \{Albert W.M.\} and Shaomin Shuang",

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

year = "2013",

month = jul,

day = "22",

doi = "10.1016/j.tet.2013.05.023",

language = "English",

volume = "69",

pages = "5874--5879",

journal = "Tetrahedron",

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publisher = "Elsevier Ltd.",

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}

TY - JOUR

T1 - Ratiometric pH responsive fluorescent probes operative on ESIPT

AU - Chan, Yim Pan

AU - Fan, Li

AU - You, Qihua

AU - Chan, Wing Hong

AU - Lee, Albert W.M.

AU - Shuang, Shaomin

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

PY - 2013/7/22

Y1 - 2013/7/22

N2 - A series of C-8′-oxime-appended spirobenzopyrans 4a-4d were synthesized and developed as fluorescent pH ratiometric probes operative in HEPES/ACN (8:2, v/v) buffer solutions. Acidochromic conversion of spirobenzopyran to merocyanine open form can facilitate the subsequent enol-keto tautomerization giving dual emissive peaks via the excited state intramolecular proton transfer (ESIPT) mechanism. The pH titrations of 4a show a 68-fold increase in ratiometric intensities ratio (I645 nm/I 522 nm) when the pH was switched from 8.0 to 4.0 with a pK a value of 5.90.

AB - A series of C-8′-oxime-appended spirobenzopyrans 4a-4d were synthesized and developed as fluorescent pH ratiometric probes operative in HEPES/ACN (8:2, v/v) buffer solutions. Acidochromic conversion of spirobenzopyran to merocyanine open form can facilitate the subsequent enol-keto tautomerization giving dual emissive peaks via the excited state intramolecular proton transfer (ESIPT) mechanism. The pH titrations of 4a show a 68-fold increase in ratiometric intensities ratio (I645 nm/I 522 nm) when the pH was switched from 8.0 to 4.0 with a pK a value of 5.90.

KW - ESIPT

KW - pH sensing

KW - Ratiometric fluorescent probe

KW - Spirobenzopyran

UR - https://www.scopus.com/pages/publications/84878886089

U2 - 10.1016/j.tet.2013.05.023

DO - 10.1016/j.tet.2013.05.023

M3 - Journal article

AN - SCOPUS:84878886089

SN - 0040-4020

VL - 69

SP - 5874

EP - 5879

JO - Tetrahedron

JF - Tetrahedron

IS - 29

ER -

Ratiometric pH responsive fluorescent probes operative on ESIPT

Abstract

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