A Zn2+-coordinated boronate dipyrrin as a chemodosimeter toward hydrogen peroxide. Issue 15 (10th March 2017)

• Record Type: Journal Article
• Authors: Sakakibara, Kaori; Takahashi, Yuki; Nishiyabu, Ryuhei; Kubo, Yuji
• Is Part Of: Journal of materials chemistry. Volume 5:Issue 15(2017)
• Page Start: 3684
• Page End: 3691
• Publication Date: 2017-03-10
• Subjects: Materials -- Periodicals; Chemistry, Analytic -- Periodicals; Optical materials -- Research -- Periodicals; Electronics -- Materials -- Research -- Periodicals; 543.0284
• DOI: 10.1039/c7tc00405b
• Languages: English
• ISSNs: 2050-7526

Abstract

Abstract : Dipyrrin derivative1 with 4-pinacolborylbenzyloxy groups was synthesized. When using Zn 2+ -coordinated1, a H2 O2 -triggered response was visually and selectively observed. Abstract : Driven by our motivation to develop a chemodosimeter for the visual detection of hydrogen peroxide (H2 O2 ), we synthesized for the first time a dipyrrin (1 ) with 4-pinacolborylbenzyloxy groups. An EtOH solution of Zn 2+ -coordinated1 was reddish-violet in color, with a λ max value of 538 nm. However, the addition of H2 O2 into the solution induced a remarkable color change from reddish-violet to blue. The time-dependent change in the absorption band showed two step kinetic processes in their kinetic profiles, where a new peak with λ max = 581 nm appeared within 13 min ( k 1 = 0.370 min −1 ), followed by a slower change in the spectra ( k 2 = 0.00371 min −1 ) concomitant with a further bathochromic shift of 18 nm. NMR and mass spectroscopic analyses indicated that the kinetically slower process may be responsible for a change in the coordination mode of the Zn 2+ ion through a H2 O2 -triggered self-immolative reaction in the 4-pinacolborylbenzyloxy groups. Basic conditions achieved through the addition of tetrabutylammonium hydroxide (TBAOH) led to the acceleration of not only the H2 O2 -triggered colorimetric change but also the turn-on fluorescence, thus allowing dual-mode sensing of H2 O2 . For practical applications, the related drop-cast paper strips were fabricated to visually detect H2 O2 vapor.