Issue 72, 2014

Synthesis of a borylated boron–dibenzopyrromethene dye enabling the visual detection of H2O2 vapor

Abstract

Given our interest in the development of reaction-based chemosensors, we developed a novel boron–dibenzopyrromethene dye with a pinacolboryl group (1), blue in color (λmax = 621 nm, ε = 8.74 × 104 M−1 cm−1) with red emission (λmax = 643 nm, λex = 550 nm) in THF. H2O2-mediated oxidation of the pinacolboryl group was found to induce a significant fluorescence decrease at 642 nm (λex = 550 nm) in EtOH/H2O (1 : 1 v/v) at 25 °C, enabling us to detect trace levels of H2O2 visually. The time-dependent response was investigated to evaluate the pseudo-first-order rate constant of 1.69 min−1 under basic conditions, meaning that its fluorescence was decreased by 80% in 2 min. Such a remarkable response capability motivated us to test the suitability of 1 for the detection of H2O2 vapor. For these experiments, a 1-coated TLC plate was fabricated by a spin-coating method and then placed in sealed bottles with H2O2 vapor. It was found that the increasing vapor concentration of H2O2 could be visually monitored by a change in red emission (ΔR value). Based on this, we estimated the detection limit of this method to be 8.43 ppb. We also found that the 1-coated TLC plate could selectively detect H2O2 vapor over common solvents tested.

Graphical abstract: Synthesis of a borylated boron–dibenzopyrromethene dye enabling the visual detection of H2O2 vapor

Supplementary files

Article information

Article type
Paper
Submitted
21 jun 2014
Accepted
13 aug 2014
First published
13 aug 2014

RSC Adv., 2014,4, 37973-37978

Synthesis of a borylated boron–dibenzopyrromethene dye enabling the visual detection of H2O2 vapor

A. Matsumoto, R. Nishiyabu and Y. Kubo, RSC Adv., 2014, 4, 37973 DOI: 10.1039/C4RA06061J

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