Issue 6, 2015

BODIPY functionalized o-carborane dyads for low-energy photosensitization

Abstract

A new type of organic dyad that can induce low-energy photosensitization has been developed; electron donor and electron acceptor units are boron dipyrromethene (BODIPY) and ortho-carborane (o-Cb), respectively. The new dyads consist of a V-shaped BODIPY-(o-Cb)-BODIPY molecular array in which two BODIPY units are substituted onto two adjacent carbon atoms of the central o-Cb. In the presence of the o-Cb unit, as an electron acceptor, significant fluorescence quenching was observed which indicated that photoinduced electron transfer (PET) had occurred from the end-on BODIPY units to the central o-Cb with PET efficiencies of 63–71%. As a result, the corresponding cationic and anionic species that are responsible for the charge transfer state were detected by the serial spectroelectrochemical studies: cationic BODIPY radicals at 400 nm at the applied voltage of 1.44 V and broad absorption bands of anionic o-Cb radicals in the range of 250–490 nm at −1.84 V. Transient absorption studies further confirmed the BODIPY radical anion at 540 nm and the o-Cb radical anion at 350–475 nm with a structureless broad band.

Graphical abstract: BODIPY functionalized o-carborane dyads for low-energy photosensitization

Supplementary files

Article information

Article type
Paper
Submitted
10 Oct 2014
Accepted
27 Nov 2014
First published
28 Nov 2014

Dalton Trans., 2015,44, 2780-2787

Author version available

BODIPY functionalized o-carborane dyads for low-energy photosensitization

G. F. Jin, Y. Cho, K. Wee, S. A. Hong, I. Suh, H. Son, J. Lee, W. Han, D. W. Cho and S. O. Kang, Dalton Trans., 2015, 44, 2780 DOI: 10.1039/C4DT03123G

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