Experimentation and theoretic calculation of a BODIPY sensor based on photoinduced electron transfer for ions detection

Hua Lu, Shu Shu Zhang, Han Zhuang Liu, Yan Wei Wang, Zhen Shen, Chun Gen Liu, Xiao Zeng You

Research output: Contribution to journalArticlepeer-review

80 Citations (Scopus)

Abstract

A boron-dipyrromethene (BODIPY)-based fluorescence probe with a N,N′-(pyridine-2, 6-diylbis(methylene))-dianiline substituent (1) has been prepared by condensation of 2,6-pyridinedicarboxaldehyde with 8-(4-amino)-4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene and reduction by NaBH4. The sensing properties of compound 1 toward various metal ions are investigated via fluorometric titration in methanol, which show highly selective fluorescent turn-on response in the presence of Hg2+ over the other metal ions, such as Li+, Na +, K+, Ca2+, Mg2+, Pb2+, Fe2+, Co2+, Ni2+, Cu2+, Zn 2+, Cd2+, Ag+, and Mn2+. Computational approach has been carried out to investigate the mechanism why compound 1 provides different fluorescent signal for Hg2+ and other ions. Theoretic calculations of the energy levels show that the quenching of the bright green fluorescence of boradiazaindacene fluorophore is due to the reductive photoinduced electron transfer (PET) from the aniline subunit to the excited state of BODIPY fluorophore. In metal complexes, the frontier molecular orbital energy levels changes greatly. Binding Zn2+ or Cd 2+ ion leads to significant decreasing of both the HOMO and LUMO energy levels of the receptor, thus inhibit the reductive PET process, whereas an oxidative PET from the excited state fluorophore to the receptor occurs, vice versa, which also quenches the fluorescence. However, for 1-Hg2+ complex, both the reductive and oxidative PETs are prohibited; therefore, strong fluorescence emission from the fluorophore can be observed experimentally. The agreement of the experimental results and theoretic calculations suggests that our calculation method can be applicable as guidance for the design of new chemosensors for other metal ions.

Original languageEnglish
Pages (from-to)14081-14086
Number of pages6
JournalJournal of Physical Chemistry A
Volume113
Issue number51
DOIs
Publication statusPublished - 2009 Dec 24

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

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