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

研究成果: Article査読

85 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)14081-14086
ページ数6
ジャーナルJournal of Physical Chemistry A
113
51
DOI
出版ステータスPublished - 2009 12 24

ASJC Scopus subject areas

  • 物理化学および理論化学

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