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

34 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

Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

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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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",

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

language = "English",

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journal = "Tetrahedron",

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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 - http://www.scopus.com/inward/record.url?scp=84878886089&partnerID=8YFLogxK

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

Scopus Subject Areas

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