Document Type

Journal Article

Department/Unit

Department of Chemistry

Title

Ratiometric pH responsive fluorescent probes operative on ESIPT

Language

English

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. © 2013 Elsevier Ltd. All rights reserved.

Keywords

ESIPT, pH sensing, Ratiometric fluorescent probe, Spirobenzopyran

Publication Date

2013

Source Publication Title

Tetrahedron

Volume

69

Issue

29

Start Page

5874

End Page

5879

Publisher

Elsevier

DOI

10.1016/j.tet.2013.05.023

Link to Publisher's Edition

http://dx.doi.org/10.1016/j.tet.2013.05.023

ISSN (print)

00404020

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