Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance upgrade on Thursday 4th of May 2017 from 8.00am to 9.00am (BST).

During this time our websites will be offline temporarily. If you have any questions please use the feedback button on this page. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 37, 2012
Previous Article Next Article

Functionalized BODIPY with various sensory units – a versatile colorimetric and luminescent probe for pH and ions

Author affiliations

Abstract

A series of BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) derivatives containing ion- and pH-sensory units have been successfully designed and synthesized. One of the compounds was structurally characterized by X-ray crystallography. Owing to the presence of an ICT absorption band, one of the compounds was found to show pronounced solvatochromic behavior in different organic solvents. Their emission energies in various solvents show a linear dependence on the Lippert solvent parameter. The cation-binding properties of the complexes with different metal ions (alkali metal, alkaline earth metal and transition metal ions) have been studied using UV-vis and emission spectroscopies. A 1 : 1 complexation to metal ions (Li+, Na+, Mg2+, Ba2+, Zn2+, Cd2+) was found for the compound with one azacrown moiety in acetonitrile while another one with two azacrown moieties was shown to form 1 : 2 complexes with Zn2+ and Mg2+ cations. Their stability constants have been determined by both UV-vis and emission spectrophotometric methods. By introducing triarylborane moieties into the meso position and the 2-position of the BODIPY skeleton, different electronic absorption spectral changes together with an emission diminution were observed in response to fluoride ions. Ditopic binding study of 5, which was functionalized with both azacrown and triarylborane moieties, showed emission enhancement in the presence of Mg2+ and F. These findings suggest that these BODIPY derivatives are capable of serving as versatile colorimetric and luminescence probes for pH, cations and F.

Graphical abstract: Functionalized BODIPY with various sensory units – a versatile colorimetric and luminescent probe for pH and ions

Back to tab navigation
Please wait while Download options loads

Supplementary files

Publication details

The article was received on 24 Feb 2012, accepted on 13 Jul 2012 and first published on 10 Aug 2012


Article type: Paper
DOI: 10.1039/C2DT30446E
Citation: Dalton Trans., 2012,41, 11340-11350
  •   Request permissions

    Functionalized BODIPY with various sensory units – a versatile colorimetric and luminescent probe for pH and ions

    Z. Yin, A. Y. Tam, K. M. Wong, C. Tao, B. Li, C. Poon, L. Wu and V. W. Yam, Dalton Trans., 2012, 41, 11340
    DOI: 10.1039/C2DT30446E

Search articles by author